Jim

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	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 First Paleto Crisis The Yakuza Crisis The Great Breakup Return of the Smuggler And others
Miscellaneous
Writer	Qocean

Background/History

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.