Jim

Background/History

Jim
Biography
Full Name	Jim Henderson
Alias(es)	The Cowboy
Gender	Male
Nationality / Ethnicity	American (South Texas)
Date of Birth / Age	1988
Place of Birth	San Antonio, Texas
Status	Alive, left Los Santos
Related to	None by blood
Affiliations
Associated Characters	Yue (girlfriend) Alexa Morrison Edward McHaggis Billy McBardigael Joey Hunt Giuseppe Marcano
Faction(s)	Lone Spurs MC
Role in Faction	President (Lone Spurs), Member (The Big Four)
Faction Status	Former leader
Timeline
First Appearance	Rise of the Syndicates
Last Appearance	The First Biker War
Key Arcs	First Paleto Crisis The Yakuza Crisis The Great Breakup Return of the Smuggler And others
Miscellaneous
Writer	User:Qocean

Jim Henderson, but always referred to as Jim, known by his nickname as "The Cowboy" and by very few as Jim Armstrong IV, is a rugged man, known for his stoic demeanour, loyalty, emotional past and rare sense of justice. He was born in 1988, in South Texas. Jim was the only son of Jim Armstrong III, who was a famous moonshiner like his father before him. The family was notorious for their expert marksmanship and their uncanny ability of deadeye shooting, something Jim learned later in his life with relative ease. His mother died during childbirth, and he never knew her. When Jim was around the age of four, his father died, possibly murdered, but Jim never discovered the truth. The only heirloom Jim got was an old outfit of his father and his signature Navy Revolver.

Upbringing with the Hendersons

His mother died during childbirth, and he never knew her. When Jim was around the age of four, his father died, possibly murdered, but Jim never discovered the truth. The only heirloom Jim got was an old outfit of his father and his signature Navy Revolver. He was placed in an orphanage and eventually adopted by the Henderson family, a cowboy clan of alcoholics who took him in primarily for the financial support. He moved to San Antonio in Texas and despite their excessive drinking, Jim embraced their lifestyle. Rodeo and firearms were a central part of their world, and Jim took to them naturally. Over time, he became part of their culture, and the Henderson family—including his cousins, aunts, and uncles—saw him as one of their own. To them, he was a true Henderson.

Despite the good relationship with his family, Jim always felt like an outsider. According to himself, he was never a true Henderson and always felt different to his family. Jim was bullied in school, as he was the only guy in his class with ginger hair. When he was young, Jim was living in his own world—he preferred reading books and practicing his gun skills with his foster father's revolver, shooting bottles and birds in the backyard when he was just eight years old, despite their pleads not to.

When he was ten years old, a new girl joined his class, Hanae Yamamoto, the daughter of a powerful Yakuza family, sent abroad to receive a better education. At first, Jim wasn’t smitten by her. But since Hanae didn’t know anyone, she approached him. It was the beginning of an unexpected and lasting friendship.

As they grew closer, the contrast in their backgrounds became more apparent. Hanae came from an above-middle-class household, living in comfort and surrounded by the elegance afforded by her father's influence. Jim, on the other hand, was living on the lower rungs of society, often fending for himself. Yet, this difference never impacted their bond. If anything, it drew them closer. Hanae's father, however, watched with growing discomfort as his daughter embraced a freer, more American lifestyle influenced by Jim.

After three years of friendship, they eventually began dating. Hanae's father disapproved, wishing she would pursue a relationship with a traditional Japanese man. Still, he believed their relationship would be short-lived. But as Hanae continued to Americanize through their relationship, her rapport with her father deteriorated.

Moving to Los Santos

At eighteen, the couple graduated high school. Jim, eager to leave his past behind, wanted to move west to Los Santos. He asked Hanae to come with him. She hesitated, afraid of defying her father. Jim reminded her firmly that it was her life—not her father's. After a heavy argument, Hanae made the choice to break contact with her family and followed Jim to Los Santos.

In the city, they bought a modest house on Sustancia Road. Jim found work as a garbage collector to support them financially while Hanae studied to become a primary school teacher. A year later, they got married.

Their wedding was very modest, attended only by a few of Jim’s colleagues and a handful of Hanae’s friends. Over the following years, Jim switched jobs frequently, working as an electrician, plumber, taxi driver, construction worker, and bike mechanic to keep their household afloat. Hanae graduated when Jim was 23, and during the period between the ages of 23 and 27, the couple tried to conceive a child.

At 25, Jim and Hanae were overjoyed to learn she was pregnant. Their daughter was born healthy, but tragedy struck three months later—she died suddenly from crib death. The loss devastated the couple. Though they never blamed each other, Jim, deep in his heart, always carried a sense of guilt over the loss. It was a wound that never fully healed.

When Jim was 28, he was working as an IT-helpdesk employee. One night, a group of masked men raided their home and violently abducted Hanae. Jim was pinned to the ground and brutally beaten. Despite the assault, he managed to fight back—kicking one of the assailants in the groin and shooting him with lightning reflexes using his pistol. He quickly shot two more intruders before rushing outside, but the van carrying Hanae had already sped off into the night.

Defeated but not broken, Jim returned inside to grab more weapons, including his signature Navy Revolver. There, he found one of the masked men still breathing. Under gunpoint and through gritted teeth, he interrogated him, eventually learning that the "target"—his wife—was being taken to a warehouse on South Shambles Street. Jim jumped into his grey Übermacht Sentinel and raced toward the location.

When he arrived, he found the warehouse, guarded by several Yakuza members already under attack by a local biker gang known as the Lost MC. Rage consumed him. Without hesitation, Jim stormed the building and shot down every armed man he encountered. Blood and chaos surrounded him, but when he finally reached the back room—it was too late. His wife, Hanae, lay dying, a gunshot wound in her abdomen. She died in his arms. Jim was heartbroken. Something inside him snapped. A vengeance-fuelled instinct emerged. He vowed to take revenge on everyone responsible for Hanae's kidnapping and murder. He buried her at the Los Santos cemetery.

Joining Lone Spurs MC

After he buried his wife, Jim left his job and fell into a deep depression that lasted for a year. He isolated himself, spending days alone and nights haunted by what had happened. The guilt consumed him. He kept replaying the events in his head—what if he had moved faster? What if he had done more? Could it all have been avoided?

One night, Jim was quietly drinking in a dimly lit bar on the east side of Los Santos when a group of cowboy-bikers walked in. They were members of a local biker gang known as the Lone Spurs MC. Jim, already cautious and guarded, tried to ignore them.

Not long after, a Vagos gang member at the bar began harassing a woman who was trying to enjoy her drink alone. When it became clear that no one else was going to intervene, Jim stood up. With a quiet fury, he grabbed the Vagos thug by the back of the head and slammed it into the bar counter, drawing the attention of everyone in the room. Before the thug could react, Jim threw him out of the bar. The woman fled, shaken but unharmed.

The bar fell silent. Jim sat back down, expecting backlash—but instead, he caught the eye of the Lone Spurs MC president, an older man with a gravelled voice and a steady gaze. The president called him over. Jim, reluctant but intrigued, joined their table. They talked—about loss, anger, justice.

Jim shared pieces of his story, not everything, but enough. The president listened and then extended an offer. He invited Jim to visit the Lone Spurs clubhouse, to see the kind of brotherhood they offered. Jim, with nowhere else to turn and still burning with silent rage, accepted.

Not long after visiting them, Jim officially joined the Lone Spurs MC, based on Popular Street near the Olympic Freeway. His skills—especially with firearms, bike mechanics, and quick improvisation—quickly drew attention from higher-ranked members. He was soon promoted to Enforcer, tasked with upholding the club’s internal Code of Honor. This code would later evolve into the foundation of Jim's own personal code.

Jim embraced the brotherhood. For the first time in a long while, he felt like he belonged. As the years passed, he marked his skin with tattoos that reflected his journey—symbols of pain, loyalty, and transformation. He grew more rugged, more self-reliant, hardened by the road.

Four years later, Jim rose to become the President of Lone Spurs MC. The club remained small and relatively insignificant in the grand scheme of Los Santos’s criminal scene. But Jim had no ambitions of turning it into a criminal powerhouse. It was his club—his sanctuary—and he kept it clean of major criminal enterprise. He was content.

Stepping into the underworld

It was during this period that Jim met Billy McBardigael, a Dutch construction contractor with subtle but deep ties to the criminal underworld. The two became fast friends. One day, Billy offered Jim a chance to do some "zwart werk"—illegal work, off the books, within his construction business. Jim hesitated. The weight of the decision pressed down on him. He knew once he crossed that line, there was no turning back. But the law had failed him too many times, dismissing Hanae's case as too complicated and without leads. If he was going to find out what really happened, it would have to be through the criminal underworld itself. With a heavy but resolute heart, Jim accepted Billy’s offer.

Jim’s slow descent into the criminal world began here. He helped Billy move illegal goods, carefully and quietly. It was through Billy that Jim was introduced to Alexa Morrison—the CEO of Liberty Exports, a logistics and property management company based in Hawick. Though legitimate on the surface, Liberty Exports was the operational front for a sophisticated underground network. Alexa was no ordinary executive; she was a syndicate leader.

Together, Jim, Alexa, and Billy formed a regional alliance called the Locals. Operating primarily from a hub on Route 68, the Locals coordinated smuggling runs and protection activities across San Andreas. As business expanded, Jim’s wealth grew. With it came smarts investment—into both criminal and legal enterprises.

He purchased and renovated the Videogeddon Arcade in La Mesa, outfitting it with a hidden basement used for heist planning. He also acquired a salvage yard in Murrieta Heights and a custom auto shop on Popular Street. But his biggest investment—and eventual pride—was The Palace, a luxurious nightclub in Del Perro.

The Palace quickly became one of the most popular nightspots in Los Santos, attracting youth, middle-class partygoers, and even the elite. Its most frequent DJ was the Blessed Madonna, a celebrated icon who elevated the club’s reputation. Jim operated primarily from this location, while continuing to live in his house on Sustancia Road, on the other side of the city. The Palace was more than a business—it was a symbol. A monument to everything Jim had built, and everything he had survived.

In late 2023, Edward McHaggis arrived in Los Santos, summoned by his cousin Billy McBardigael. He showed up with a half-packed duffel bag, casually clothed, seemingly ready for a party and carrying a head full of ideas. Jim and Alexa were already waiting for him at a private house in Vinewood Hills, where the introduction was made. Jim immediately offered him a drink—an act Edward instantly appreciated. The gesture sparked an immediate liking for Jim. Despite the good vibes, the atmosphere in the room remained skeptical and tense—who was Edward really, and what were his intentions? Edward cleared the air by revealing that he had previously been a member of both the Yakuza and the Cosa Nostra. He wasn’t a rookie, and it showed. While Alexa remained reserved, Jim stayed quiet but attentive, feeling a kind of familiarity in Edward’s ambitions. Edward had moved to Los Santos to build a better life for his wife—a hope Jim once carried, but now could no longer offer.

Edward soon joined the Locals and began building his own businesses. Jim got along with everyone, largely due to his neutral stance. He never passed judgment without reason and often acted as a stabilizing force, bridging the gaps between differing perspectives within the group.

Just as the Locals began growing into a real presence, tragedy struck—Billy passed away from terminal lung cancer. His death left a deep void. Jim mourned his friend but chose to honour his legacy through work. He closely supported Billy’s longtime business partner, Tony, who stepped in to continue what Billy had started.

With Edward, Alexa, and Tony, Jim helped formalize their collective operations into a structured alliance. This new collaboration became known as the Big Four. Jim believed in its necessity—if they were going to grow and influence the region, they would need to do it together, united in purpose.

Event of GTA RP

First Paleto Crisis

During the First Paleto Crisis, Jim played a pivotal role in the interrogation of Damian Morrison, the leader of the upcoming Bay Rebels. Jim, along with Edward and Tony, kidnapped Damian and subjected him to a brutal interrogation in an alley on Mutiny Road. Damian, despite his inexperience in the criminal world at the time, held a deep-seated grudge against Jim from the very moment he met him. Jim, seeing potential in Damian but unwilling to let weakness persist, played the 'bad cop' role, ensuring Damian understood the stakes of his involvement in the criminal world. Though Jim was far from being the most ruthless of the group, he made it clear that any sign of weakness would be exploited. The events of the interrogation left Damian scarred, fueling his later vendetta against Jim and the syndicates in the city.

As time passed, Jim found himself reflecting on that night more often than he cared to admit. What had once seemed like a necessary show of force now felt like a reckless act, a mistake born out of the syndicates' need to assert dominance. He realized that torturing Damian had been unnecessary. It hadn't deterred the kid, it had only given him more reason to fight back. Jim regretted it, not because he feared retribution, but because it had been avoidable. Damian could have been handled differently, and now, Jim had no doubt that the grudge Damian carried would one day come back to haunt them all.

After the interrogation, Edward and Tony saw Damian as a loose end that needed to be dealt with, but Jim wasn’t convinced. Killing him seemed unnecessary, and when he learned Damian was Alexa Morrison’s twin brother, it became clear that eliminating him would cause more problems than it solved. Alexa made it clear that she wouldn’t stand idly by if Damian was killed, and Jim knew better than to push her on it.

Rather than escalate an internal war, Jim chose neutrality, refusing to take part in Damian’s execution. Edward saw this as disloyalty, while Alexa took note of Jim’s restraint. In the end, Jim had no regrets, killing Damian would have only ignited a conflict they weren’t ready for (a conflict with Alexa). Sometimes, knowing when not to act was the smartest move.

The Interbellum

Following the First Paleto Crisis, a tense period of uncertainty settled over the syndicates. The city’s criminal underworld was shifting, alliances were becoming strained, and Jim found himself caught between growing tensions. With Damian out of the picture, at least for the moment, the focus shifted toward consolidating power and fortifying existing operations.

During this time, Giuseppe Marcano entered the scene and introduced the concept of the Commission—a structured criminal network meant to regulate disputes and maintain order among the major syndicates. While Edward saw this as a way to strengthen his own influence and Alexa carefully analyzed its potential, Jim remained skeptical. He had never been one for rigid hierarchies and wasn’t sure if Giuseppe could be trusted, but he and the others decided to give the Commission a shot anyway. Still, he saw it as just another bureaucracy that would eventually crumble under the weight of competing egos.

Jim used the Interbellum period to further reinforce his own operations, by buying new businesses and equipment, ensuring that whatever happened with the Commission, he wouldn’t be left vulnerable. He maintained his neutrality, avoiding unnecessary entanglements while keeping a close eye on how things unfolded. Edward, eager to establish his power, pushed for aggressive expansion, while Alexa worked quietly in the background, securing her own position. Jim, however, stayed the course, choosing patience over ambition.

As the dust settled from the Interbellum, Tony abruptly left, distancing himself from the syndicate conflicts entirely. Meanwhile, in a bizarre turn of events, Billy McBardigael was resurrected through an unconventional ritual, returning to the criminal world as if he had never left. Jim, ever the pragmatist, didn’t waste time questioning the how or why—Billy was back, and that meant another unpredictable force in the underworld. While Edward welcomed Billy’s return, Jim remained cautious, recognizing that this development would inevitably shift the balance of power once again.

Second Paleto Crisis

As tensions continued to rise, Damian Morrison returned to San Andreas, re-establishing the Bay Rebels with a newfound sense of purpose. His return reignited old conflicts, and the syndicates once again found themselves at odds over how to deal with him. Edward and Tony, still holding onto their grudge, wanted Damian eliminated once and for all, while Alexa remained distant but watchful.

Jim, as before, refused to be drawn into the blood feud. He saw the conflict brewing and understood that jumping into the fight would only destabilize the fragile balance that had been maintained. Instead, he focused on protecting his interests, ensuring that his businesses and supply lines remained untouched by the chaos in Paleto Bay.

However, luck wasn’t on Jim’s side, as Damian developed a personal grudge against him, believing that Jim and Alexa shared a romantic interest, which was never the case. Fueled by misplaced resentment, Damian targeted Jim’s operations in Grapeseed, launching attacks on his supply lines and forcing him into defensive skirmishes despite his initial efforts to stay neutral.

While Jim still avoided taking an offensive role in the conflict, he had no choice but to defend what was his. Rather than escalating the situation further, he reinforced security and ensured that his operations in Grapeseed could withstand the attacks. His neutral stance was now compromised, but he remained focused on keeping the war from directly consuming his business interests.

The conflict reached its peak when the syndicates, excluding Alexa, launched an assault on Paleto Bay to put an end to Damian’s rebellion. Jim played a supporting role, handling logistics for the others while personally ensuring that Damian wouldn’t escape. When Damian attempted to flee by air, Jim took part in shooting down his plane, ensuring the conflict was decisively ended. Though his involvement had been limited, it was clear that Jim could no longer rely on neutrality alone in the shifting underworld of San Andreas.

After the conflict ended in a stalemate, Damian and Cash recognised their disadvantage and disagreed the Bay Rebels. They both flew to Vice City for pastures new.

The Yakuza Crisis

Following the events of the Second Paleto Crisis, the balance of power in the criminal underworld once again shifted. This time, the focus was primarily on Edward, as the Yakuza placed a financial burden on him, because of his history with the Yakuza and refusing to cut off his finger. This eventually caused a disruption in all syndicate operations rather than engaging in open conflict. Their resurgence came in the form of an economic stranglehold—seizing shipments, blocking trade routes, and imposing an embargo on all syndicate-controlled goods.

For Jim, this conflict was far more personal. His past with the Yakuza, tied to the murder of his wife, had never truly been put to rest. Unlike Edward, who was focused on resolving the financial strain, Jim had a deep-rooted hatred for the organization. While others viewed the crisis as a logistical challenge, Jim saw it as an opportunity to take the fight directly to them. However, the other syndicates were more cautious, knowing that direct confrontation with the Yakuza could be disastrous.

With the embargo tightening, the syndicates held a meeting to discuss a solution. The proposal on the table was hiring Hans Naumann, a skilled smuggler with the expertise to bypass the Yakuza blockade. The price: 5% of all syndicate income. Jim strongly opposed the idea, believing that taking aggressive action against the Yakuza was the only way to break their hold. However, he was ultimately outvoted 3-1, and Hans was brought in to handle smuggling operations.

Despite his reluctance, Jim had no choice but to work with Hans as the syndicates adapted to the new circumstances. While he disliked relying on an outsider, the smuggler proved effective, ensuring that essential goods continued to flow despite the Yakuza’s efforts. However, Hans’s lack of professionalism became evident when the Yakuza managed to steal a USB stick containing sensitive data on the syndicates and their customers from his safehouse in Bay City Avenue. Jim openly called out Hans for his failure to encrypt the data, considering it a reckless mistake that put everyone at risk.

The crisis came to a brutal end when Billy McBardigael, acting alone, drilled into the Land Act Reservoir facility, the Yakuza's headquarters in Los Santos, and massacred hundreds in a single night. Their leadership wiped out, the Yakuza’s influence crumbled instantly. Edward was relieved, while Jim found the outcome both unexpected and satisfying, though not the strategic fight he had envisioned. Still, he knew such reckless actions rarely came without consequences.

During the chaos, Alexa secretly retrieved the stolen USB stick, copying its contents to a hard drive in her agency before returning it to Hans. Jim, unaware of her actions, was already frustrated with Hans’s incompetence and how the syndicates had handled the situation.

The Revelation and Confrontation with Hans

After Alexa returned the USB stick to Hans, she took the time to analyze the data she had copied. What she found disturbed her, hidden within the files was evidence that Hans had been involved in the kidnapping of Jim’s wife years ago. He had accepted a contract for the operation from the father of Jim’s wife, to deliver her to the warehouse where she met her fate.

Alexa called Jim and told him that he needed to see something at her agency. There, she revealed everything with proof. The revelation shook Jim to his core. He had despised the Yakuza for years, holding them responsible for his wife’s death, but now he learned that Hans had played a direct role in her suffering. Jim wasted no time and arranged a meeting with Hans, under the cover of a 'concluding business meeting', at the Galileo Observatory.

At the meeting, Jim confronted Hans, leveling his classic Navy Revolver at him. Hans immediately recognized the weapon as the heirloom of the famous Armstrong family and tried to ask about its significance, but Jim cut him off, making it clear that this was not a conversation, this was judgment. Hans, sensing his fate, spoke calmly, asking Jim if it was worth killing off another family, reminding him of the cycle of violence he had been trapped in for years.

Jim hesitated. Everything in him told him to pull the trigger, to avenge his wife. But as he stared Hans down, he realized that revenge had never brought him peace before, and it wouldn’t now. In the end, Jim lowered his revolver and spared Hans, warning him never to return to Los Santos. Hans, understanding the gravity of the situation, left without another word.

Though Jim had let him live, the encounter left him unsettled. He had spent years chasing ghosts, seeking retribution, but for the first time, he had chosen restraint. Whether it was wisdom or weakness, only time would tell.

The Ron and Archie Plot

With the Yakuza and Hans gone, the Big Four resumed business. However, law enforcement in Blaine County became an unexpected obstacle. Two new officers, Sergeant Ron Milliken, a former coworker of Jim’s from their days as mechanics, and Deputy Archie Calloway, joined the Sheriff’s Department in Sandy Shores. Their highlight was the capture and subsequent death of the infamous Slasher, earning them a promotion.

Sometime later, Ron and Archie began investigating Pixel Pete’s, Damian Morrison’s former arcade in Paleto Bay, and stumbled upon a case file on the syndicates. Recognizing the scale of the criminal network, they decided to pursue the case further, without informing the Sheriff, whom they suspected of corruption.

The syndicates quickly caught wind of the investigation and saw the danger it posed. Seeing Jim as the least likely suspect, they pressured him into handling the situation. Jim was reluctant, knowing that killing law enforcement would escalate tensions, but in fear of losing support from the others in their already shaky relationship, he ultimately agreed. Rather than risk prolonged exposure, they devised a trap to eliminate the threat before it could grow. The plan was set in motion near the Yellowjack Bar, where a staged gang shootout was used as bait. When Ron exited his car to investigate, Jim remotely detonated a car bomb planted in the vehicle, instantly killing Archie. As Ron reeled from the explosion, severely wounded and barely able to move, he looked up and saw Jim approaching. Through gritted teeth, he muttered, "You? I didn't expect you to be one of them." Coughing blood, he stared at Jim, his voice weak but resolute. "Justice will catch up with you... one day."

Jim stood over him, silent for a moment, before raising his gun. Knowing there was no saving Ron, Jim aimed and pulled the trigger, delivering a mercy kill to end his suffering.

Afterward, as the dust settled, a heavy sense of regret crept over Jim. He had killed many men before, but this was different. Ron had not been corrupt for personal gain, he had bent the law to fight true corruption, to protect the people of Blaine County. Though they had never been friends, Jim couldn’t shake the feeling that he had just ended the life of a good man, someone who had once worked beside him in a different life. The weight of that decision lingered, another ghost to haunt him in a city where sins were never truly buried.

The Great Breakup

Jim had known for a while that the Big Four was coming apart. The Ron and Archie incident had only widened the cracks, and there was no trust left between them. He had tried to keep things balanced, but diplomacy no longer worked.

After the deaths of the Blaine County officers, there was a brief period of peace, but Jim knew it wouldn’t last. When Giuseppe returned to Los Santos on October 27, 2024, he seemed done with syndicate politics. Edward tried to pull him back in, but Giuseppe refused.

Edward was struggling to hold onto Claymore MC. Members were leaving, and when Billy and Edward brought in a newcomer, Jeff Cooper, an ambush at an abandoned government facility confirmed that defectors had turned against them. These defectors formed their own motorcycle club; the Alamo Hellraisers. Tensions escalated further when Claymore MC and Billy retaliated against the Alamo Hellraisers, a move Jim watched from the sidelines, knowing it was leading toward something worse.

On November 8, Edward called a Big Four meeting. Alexa doubted his ability to control the situation, and Edward, already unstable, lashed out. Later that night, Jim met with Edward at Videogeddon and suggested Alexa was trying to stop another war. But Edward had already made up his mind—diplomacy was over.

Billy, meanwhile, had his own revelation. That night, he met the Alamo Hellraisers’ leaders and learned that Edward had abandoned two of his own men. To Billy, betrayal was unforgivable. He called for a meeting, and Jim already knew what was coming. Billy declared that money had destroyed their friendship and left the Big Four. Edward followed. Jim sat there for a moment, taking it all in. Then, without a word, he stood and walked away. Alexa, the last one at the table, eventually did the same. This marked the end of the formal alliance between the four. Despite the collapse, Jim remained on good terms with everyone, and while the others suffered heavy losses in the fallout, the breakup hit him minimally. His neutrality ensured he walked away with his businesses intact and his influence unshaken.

In the aftermath, Claymore MC fell apart. Edward’s business empire crumbled in a mutiny, and only Jeff and Jim stayed with him. Jim helped where needed but kept his distance, refusing to be pulled into the wreckage.

Giuseppe returned shortly after and quietly reclaimed Paleto Bay. His silent takeover angered Alexa, who saw it as opportunism, but Jim only watched. The fractures between them all had only grown wider.

Jim, however, did what he had always done best; he adapted. The Big Four were gone, but he was still standing. While others fought for dominance, he secured his businesses, cutting ties where necessary and ensuring that whatever came next, he would not be caught off guard.

The underworld of Los Santos had changed, but Jim knew one thing for certain; this was far from over. The city never stayed quiet for long, and sooner or later, the past would come knocking once again.

Return of the Smuggler

On March 5th, Jim was returning to his residence on Sustancia Road when he was contacted by Alexa Morrison and instructed to meet her immediately in Del Perro. The urgency in her request stood out, as she provided no context beyond the location and insisted on haste. Jim complied without delay.

Upon arrival at the coast, Jim was transported by helicopter to a yacht anchored offshore. There, Alexa presented him with an audio recording delivered earlier by an anonymous courier. The recording featured a distorted voice identifying itself as "the Phantom" and contained clear evidence that Marty Marcano had been abducted and was being actively tortured. The contents of the tape confirmed that the situation was ongoing and severe.

The revelation marked a notable shift in Alexa’s composure. For the first time since Jim had known her, she lacked clear control over the situation. Jim assessed the circumstances with visible restraint. Only two weeks earlier, his own residence had been attacked in an incident involving Marty and an associate named Morgan, leaving him disinclined to intervene on Marty’s behalf.

Despite his reservations, Jim ultimately agreed to assist in locating Marty. His decision was pragmatic rather than sympathetic, driven by the understanding that unresolved instability surrounding the Marcano family and the Phantom posed a broader threat. After leaving the yacht, Jim contacted Edward McHaggis to brief him on the situation. Edward, who had already returned to San Andreas on February 20th following the failure of the First Scottish Revolution, agreed to assist.

Jim then returned home, minimized contact, and prepared for what he anticipated would be a prolonged and dangerous operation.

Looking for Marty

On the morning following the meeting with Alexa, Jim met Edward at an airfield in San Andreas. Edward had already been back in the country for several weeks, though this marked his first direct involvement in Jim’s affairs since his return from Scotland. The effects of his time abroad were evident. While he remained composed and deliberate, his demeanor reflected the consequences of defeat and prolonged conflict.

Jim arrived using his modified Terrorbyte, outfitted with surveillance systems, drone support, defensive countermeasures, and long-range operational equipment. From there, the two proceeded toward the Darnell Brothers Garment Factory in La Mesa, which had recently been acquired by Marty Marcano and served as a logical starting point for reconstructing his recent activities.

During transit, Jim and Edward reviewed developments within the criminal landscape of Los Santos, including the dissolution of former alliances and the growing instability tied to the Marcano family. Edward provided limited insight into the failed Scottish Revolution, framing it as a decisive loss that carried lasting personal and strategic consequences. Jim noted that the experience had altered Edward’s outlook, though the precise nature of that change remained unclear.

As they approached La Mesa, both men understood that any information uncovered at the garment factory would likely extend beyond Marty himself. The investigation was not limited to a disappearance, but to the emergence of a wider and more dangerous network operating in the background. Over the following days, Jim committed to methodically retracing Marty Marcano’s actions, contacts, and financial movements, anticipating that the search would draw him further into an escalating conflict tied to the Phantom and the broader power shifts within San Andreas.

Escalation at McKenzie Airfield

Roughly five days after Jim and Edward began retracing Marty Marcano’s movements, the effects of outside interference became increasingly visible. Syndicate-controlled drug markets began to falter, with sales dropping sharply and distribution routes showing signs of disruption. The pattern suggested deliberate manipulation rather than coincidence.

Information relayed by Alexa Morrison pointed toward a growing presence in Grapeseed, centered around McKenzie Airfield. Given their history with the region, Jim and Edward initially suspected the Alamo Hellraisers. Early surveillance, however, failed to substantiate that assumption.

Operating independently, Jim drove the Terrorbyte to the airfield while Edward conducted aerial reconnaissance using a drone. It was Edward who made the identification. He observed Hans Naumann at the field, actively preparing a Duster 300-H aircraft, and immediately relayed this to Jim. The confirmation came as a shock. Hans’s presence marked a direct violation of Jim’s earlier warning and confirmed that he had returned to San Andreas without restraint.

Jim reacted instinctively. Despite Edward urging him to slow down and reassess the situation, Jim exited the vehicle and attempted to stop the aircraft before takeoff. His response was uncharacteristically impulsive, driven by a surge of anger tied to Hans’s past involvement in his life and the growing suspicion that Hans was once again destabilizing everything around him. Hans responded with speed and precision, getting the aircraft airborne under fire and escaping the airfield before meaningful damage could be inflicted.

Jim immediately informed Alexa of Hans’s return and escape. Alexa’s concern shifted sharply toward Marty Marcano, and she voiced her belief that Hans was directly connected to his disappearance.

Three days later, Jim and Edward returned to McKenzie Airfield to continue their pursuit. This time, the situation escalated further. Edward detected a heavily armed cargo aircraft on radar, indicating that Hans had significantly expanded his operational capabilities. Jim engaged using the Terrorbyte’s missile systems, while the opposing aircraft returned fire with a mounted 40mm weapon. After sustaining damage, Hans withdrew toward Fort Zancudo rather than risk destruction.

Not long after disengaging, Jim and Edward were attacked by a B-11 Strikeforce. Based on the timing and the nature of the engagement, both believed Hans himself was piloting the jet. The pursuit carried over the Alamo Sea before ending without a decisive outcome.

In the aftermath, Jim and Edward encountered one of Hans’s operatives on the ground. The man was detained at gunpoint and admitted to working for Hans Naumann. When pressed for further information regarding Hans’s return and Marty Marcano’s location, the operative refused continued cooperation and ultimately took his own life, leaving Jim and Edward without additional intelligence.

Jim reported the engagements and developments to Alexa. Recognizing the severity of the situation, she advised Jim to contact Giuseppe Marcano directly. Jim informed Giuseppe that his son had been abducted and that Hans Naumann was involved. Giuseppe reacted with immediate fury and pledged his full support in recovering Marty and dealing with Hans by whatever means were necessary.

For Jim, these events marked a turning point. What had begun as a controlled investigation gave way to open confrontation. His brief loss of restraint at McKenzie stood in contrast to his usual discipline, underscoring how deeply Hans’s return—and Marty’s disappearance—had cut into his carefully maintained control.

The Observatory Confrontation and Market Collapse

In the days following the confrontations around McKenzie Airfield, Hans Naumann executed what was widely regarded as the largest smuggling operation in the history of San Andreas. The deal generated millions in profit and flooded the market with narcotics, driving prices to an unprecedented low. The sudden collapse destabilized existing supply chains and undercut nearly every major distributor in the region, including Jim’s own operations. The disruption caused widespread frustration among criminal factions, with many viewing Hans’s actions as having deliberately thrown roet in het eten for an already fragile balance.

For Jim, the impact was immediate and severe. Years spent cultivating controlled distribution routes and stable pricing were undone in a matter of days. While the financial loss was significant, what angered him more was the recklessness of the act. The move reinforced his belief that Hans operated without regard for long-term consequences, driven solely by personal gain.

Unbeknownst to Jim at the time, the smuggling operation had been carried out in secret collaboration with Edward. Edward, facing mounting financial pressure related to plans for a second revolutionary effort abroad, had agreed to assist Hans in exchange for funding. On the morning of March 30, Hans and Edward met privately at Thomson Scrapyard in the Grand Senora Desert. During this meeting, Edward assured Hans that his life would be spared. In return, Hans committed to supplying Edward with weapons and logistical support as a form of repayment.

Only hours later, Alexa independently tracked Hans’s movements and determined that he was visiting the Observatory. Recognizing the opportunity, she immediately contacted Jim. Jim, in turn, reached out to Edward, and both men moved to intercept Hans.

At approximately 16:00, Jim and Edward confronted Hans at the Observatory. Hans appeared unsurprised by their arrival. Jim confronted him at gunpoint, his intent clear. The encounter escalated rapidly when Hans revealed that he possessed leverage: Marty Marcano was alive and being held safely by his employer. The revelation stalled Jim long enough for the situation to shift.

As Jim prepared to act, Edward turned his weapon on Jim instead, revealing the agreement he had made with Hans earlier that day. Edward insisted that Hans be kept alive in order to preserve the weapons deal tied to his revolutionary plans. The disclosure marked a profound rupture for Jim. In that moment, he was forced to confront not only Hans’s survival, but Edward’s direct involvement in both the market collapse and Hans’s continued freedom.

Hans, emboldened by the situation, openly acknowledged Edward’s role in the smuggling operation and implied that Jim’s conflict with him should be considered resolved after nearly nine years. He used the moment to undermine Jim’s trust, suggesting that loyalty within their circle had always been conditional.

With neither Jim nor Edward acting further, Hans departed the Observatory, escaping by motorcycle and disappearing into the city. The encounter, later referred to by those involved as the Observatory Incident, left Jim deeply disillusioned. What had begun as a pursuit of a common enemy ended with the realization that betrayal had come from within.

For Jim, the incident solidified a lasting shift in perspective. The collapse of the narcotics market, Edward’s duplicity, and Hans’s continued survival reinforced his growing distrust of alliances built on convenience rather than principle. From that point forward, Jim became increasingly guarded, more selective in his cooperation, and far less willing to compromise his code for the ambitions of others.

Aftermath and Dissolution of Trust

In the immediate aftermath of the Observatory Incident, Jim confronted Edward privately and demanded an explanation for the arrangement with Hans Naumann. Edward admitted that the decision had been driven by desperation. He required substantial funds and access to weapons in order to finance and supply a second revolutionary effort abroad, and viewed the deal with Hans as a necessary compromise. The explanation did little to ease the damage. Jim made it clear that Edward’s actions had irreparably undermined his trust and friendship, not only by protecting Hans, but by involving Jim—unwittingly—in the consequences of the deal.

Following the confrontation, Jim withdrew entirely. He returned alone to his home on Sustancia Road, where he spent the night drinking heavily. The incident forced him into prolonged introspection. For the first time, he fully accepted that he would never be able to avenge his wife’s death. Hans’s survival had closed that path permanently. As the night wore on, Jim questioned not only Edward’s motives, but his own decisions. He repeatedly revisited the moment at the Observatory, wondering whether Edward’s actions had been calculated from the beginning and what the outcome might have been had he chosen to pull the trigger.

In the early hours of the morning, Alexa arrived at Jim’s home unannounced. Jim, visibly exhausted and in poor condition, allowed her inside. She immediately pressed for answers, asking whether Hans was dead. Jim confirmed that Hans was still alive, that Marty Marcano remained in captivity under Hans’s employer, and that Edward had effectively sided with Hans in exchange for an arms deal. The revelation stunned Alexa, though it did not entirely surprise her. Her concern remained focused on Marty’s safety and the uncertainty of what would follow.

As the conversation continued, Jim reached again for a bottle of whiskey, prompting Alexa to confront him directly. She criticized his withdrawal and warned him against allowing loss and regret to consume him. With no further discussion, she left for her office, leaving Jim alone with the consequences of the night.

The Yakuza Resurgence

In the period following Hans Naumann’s departure, Jim became increasingly aware that a new and more methodical threat was forming beneath the surface of Los Santos. Intelligence later confirmed that a Yakuza cell had re-entered San Andreas with the explicit objective of weakening the remaining syndicates and, ultimately, eliminating Edward McHaggis. While much of their early movement occurred outside Jim’s direct awareness, several of their actions intersected with his life and operations in significant ways.

During the initial phase of the resurgence, Yakuza operatives conducted reconnaissance across the city, identifying key locations tied to syndicate leadership and infrastructure. Among the sites observed were Jim’s residence on Sustancia Road and his arcade and auto shop operations, placing him firmly within their operational scope. Though Jim was not confronted directly at this stage, he later recognized that the surveillance had been deliberate and thorough.

Jim’s first direct interaction with the resurgent Yakuza came through a woman operating under the alias “Yeorum,” who encountered him at the Yellowjack Inn after his Übermacht Sentinel experienced mechanical issues. Presenting herself as a recent arrival to San Andreas, she assisted Jim with repairs while covertly installing a tracking device on the vehicle. Jim, already suspicious of her presence and timing, chose not to confront her. Instead, he played along and invited her to assist with routine work at his auto shop the following day, allowing him to observe her more closely.

At the auto shop, Jim spent several hours with “Yeorum” while completing client deliveries. During this time, he spoke openly about his upbringing with the Henderson family, his history of manual labor, and the circumstances surrounding his late wife. Though his manner remained calm and accommodating, Jim did not fully trust her. After parting ways, he became increasingly convinced that her interest in him was professional rather than personal.

As events unfolded, Jim learned that the Yakuza cell had fractured internally. Acting against direct orders from their leadership in Japan, elements within the group prioritized pursuing Edward independently. When Edward was later approached by Yakuza representatives and offered protection in exchange for cooperation, he contacted Jim to inform him of the encounter. The conversation was strained and unresolved. Edward made it clear that he no longer intended to involve himself in syndicate affairs, leaving Jim with the growing certainty that Edward was no longer an ally—and perhaps never truly had been.

Concerned by the narrowing space around the syndicates, Jim sought out Giuseppe Marcano at the headquarters of Giuseppe & Co. in Rockford Hills. The two exchanged information regarding Marty’s kidnapping, the Yakuza’s movements, and Edward’s increasingly erratic behavior. Giuseppe openly expressed disappointment in Edward, describing him as fractured and unrecognizable following his failed revolution abroad. Jim and Giuseppe agreed to keep one another informed, recognizing that cooperation was now a matter of survival rather than ambition.

The turning point came when “Yeorum” appeared unannounced at Jim’s home. Visibly distressed, she confessed her true identity as Yue, a Yakuza operative tasked with gathering intelligence on Jim and Alexa Morrison. She revealed the internal collapse of the cell, including the murder of one of her own by its acting leader, and disclosed the location of a Yakuza submarine stationed off the coast near Chumash.

Jim listened without interruption. He felt genuine sympathy for Yue, not only because of her honesty, but because he recognized the fear and isolation behind it. He became aware that Yue harbored a quiet affection for him—something she never stated outright, but which was evident in her behavior and willingness to risk her own life by coming to him. Despite the danger her presence represented, Jim chose to offer her temporary protection, insisting on full honesty going forward. Before leaving, she provided her real name, confirming Jim’s suspicions.

Jim immediately relayed the information to Alexa and met with her the following morning at her office in Maze Bank Tower. From Alexa’s perspective, Yue represented an unacceptable risk. She viewed Yue not as a defector, but as a compromised operative whose previous actions had already endangered her organization. Alexa ordered Jim to eliminate her without hesitation.

Jim refused. He argued that Yue’s defection, combined with the intelligence she had provided, outweighed her past allegiance and made her more valuable alive than dead. Alexa interpreted his refusal as weakness. "Is this because she spread her legs for you?" She openly accused Jim of allowing personal sentiment and his moral code to interfere with sound judgment, questioning whether his stance was influenced by Yue’s proximity to him rather than strategic reasoning. The accusation was blunt, hostile, and deliberately confrontational.

The exchange escalated sharply. Jim reminded Alexa that he had remained loyal when others had betrayed her, fractured under pressure, or abandoned their responsibilities entirely. He framed his refusal not as defiance, but as consistency—an extension of the principles that had made him reliable when others were not.

After several tense moments, Alexa relented, but only partially. She allowed Yue to live on the condition that she never appear in Alexa’s presence again. Alexa made her position unmistakably clear: if Yue ever crossed that boundary, she would be killed without discussion or hesitation.

With the intelligence secured, Jim assisted in planning the next phase, which culminated in an assault on the Yakuza submarine. While Jim did not participate directly in the final operation, he remained involved in coordination and information flow. The raid resulted in the recovery of Marty Marcano and the effective collapse of the Yakuza cell’s local operations.

For Jim, the Yakuza Resurgence reinforced several hard-earned lessons. Trust, once broken, could not be easily repaired. Alliances built on desperation inevitably failed. Most importantly, restraint and judgment mattered more than vengeance. As the immediate threat subsided, Jim emerged more isolated but also more certain of his principles, aware that the city was entering yet another cycle of violence—and that he would need to navigate it carefully.

Aftermath and Withdrawal

With the elimination of Yorinobu and the dismantling of the remaining Yakuza presence in San Andreas, the immediate crisis came to an end. Marty Marcano was recovered, and the coordinated threat against the syndicates dissolved. In the days that followed, Los Santos gradually returned to its familiar rhythm, though the consequences of the conflict lingered beneath the surface.

Three days after Marty’s liberation, on a stormy evening, Jim was alone at his home on Sustancia Road when the doorbell rang. Standing outside was Yue, soaked from the rain and wearing a bright yellow raincoat. She sought warmth, shelter, and reassurance after weeks spent in fear and uncertainty. Jim allowed her inside without hesitation.

Yue settled near the fireplace to warm herself. Once Jim secured the house, she removed her raincoat, revealing how vulnerable she truly was. In that moment, the emotional distance Jim had maintained for nearly a decade collapsed. He had not been intimate with anyone since the death of his wife nine years earlier, and the combination of exhaustion, relief, and long-suppressed desire overcame his restraint. The two shared an intimate encounter by the fire, marking a decisive emotional break from Jim’s long period of isolation.

In the weeks that followed, Jim and Yue began seeing one another in secret. Their relationship remained deliberately out of sight, though it did not go unnoticed forever. Alexa eventually became aware of it. The development did not surprise her; it merely confirmed her earlier assessment of Jim’s weaknesses and priorities. She made no effort to intervene, but the knowledge further widened the distance between them.

Jim leaving Los Santos with Yue

Over the following months, Jim’s motivation to maintain a criminal empire steadily eroded. The cycles of betrayal, violence, and compromise no longer held purpose for him. His focus shifted toward preserving the fragile stability he had found with Yue and distancing himself from a world that had taken far more than it had ever given back.

On July 17, after months of quiet preparation, Jim executed a plan he had been developing in isolation. Without informing Alexa or any of his former associates, he sold off all remaining business interests and severed his operational ties in a single afternoon. By the time news of the transactions began to circulate, Jim was already gone.

He left San Andreas with Yue and relocated to Oregon, settling in a remote cabin surrounded by forest. There, Jim withdrew almost entirely from the criminal world, spending his days walking the land, living quietly, and embracing a life defined by simplicity rather than control.

In a city where few ever truly escaped the consequences of their choices, Jim’s departure stood out. Whether by resolve, restraint, or sheer circumstance, he was among the rare individuals who managed to leave the underworld largely intact.

Personality and morality

Jim is a pragmatic, calculating figure in the San Andreas underworld, embodying the resilience and independence of a lone gunslinger. While others seek power or domination, Jim operates under a strict personal code, one that values loyalty, honesty, restraint and necessity over recklessness. Though feared for his skills, Jim is not defined by a thirst for violence. He sees killing as a last resort, a tool rather than a desire, and prefers to handle conflicts through strategy and preparation rather than brute force. While many in the underworld view his moral compass as a weakness, Jim sees it as his anchor, the one thing keeping him from losing himself entirely to the chaos and bloodshed that surround him.

Despite his hardened exterior, Jim is not entirely emotionless. He is known to be welcoming to those around him, often playing the role of a mediator in tense situations. No matter how rough the day gets, Jim always has a plate of food left over for someone who needs it, a small but significant gesture that reflects his belief in loyalty and camaraderie. He harbours a deep sense of justice, one that does not always align with traditional morality but exists nonetheless. Those who cross a line, betray trust, or exploit the weak will find themselves facing his quiet but deadly resolve. At the same time, Jim is fiercely protective of those he considers family, even if his way of showing it is through action rather than words.

Unlike his peers, Jim does not seek total control. He values independence above all else and dislikes the bureaucracy and politics that come with large criminal syndicates. However, above all, Jim values loyalty and honesty, believing that trust is the foundation of any meaningful alliance. These values are highly regarded by other syndicates, especially by Alexa, who finds Jim's unwavering loyalty and honesty both refreshing and rare. This has often placed him in the role of mediator, never fully committing to one side but ensuring that balance is maintained. His neutrality, however, has been tested time and again, especially when personal stakes are involved.

Jim's past continues to haunt him, particularly the murder of his wife, an event that shaped his approach to the criminal world. Yet, it is not the only ghost he carries. He feels deep regret for the brutal interrogation of Damian Morrison and the killing of Ron Milliken, both moments where he crossed lines he never intended to. While he no longer acts out of blind vengeance, he has never fully let go of the weight of his decisions. His restraint is not just a tactic, it is a form of survival, a way to keep from becoming just another monster in a world full of them.

In a city where power-hungry syndicates rise and fall, Jim remains an enigma, a man who plays by his own rules, refusing to be controlled yet always watching, waiting, and prepared for whatever comes next.

Jim's Code of Honor

1. Don't kill in cold blood.
2. Show mercy whenever you can.
3. Don't kill or hurt unarmed women.
4. Never betray those who have earned your trust, and always remain loyal to what truly matters: alliances, friends, and family.
5. Protect the innocent when possible, but never at the cost of those he considers family.