James Callahan
Biographical information

Jimmy C
Cadillac Jim
Jimmy the Suppressor




December 21th, 1946.

Physical description

Caucasian (Irish descent)



Hair color

Black, graying

Eye color


Skin color


Familial and political information
Known family

Pauline Callahan (Mother)
Patrick Callahan (Father)


The Callahan Mob

Miscellaneous information

Irish mob boss

Owned vehicles


"James Callahan" (born December 21st, 1946) and better known as "Jim" or "Jimmy C" amongst the neighborhood of Ocean Flats, San Fierro, is an infamous Irish-American mobster recognized by the Federal Bureau of Investigation as the leader of the Callahan Mob. Beside his close friend and criminal associate, Gerald Sullivan, the two had rised to the top of the food chain in the San Fierro area. Both heavilly influencing the neighborhood with crime ranging from extortion, murder, and armed robbery.

Early LifeEdit

James had grown up in the 1950s during the near-end of Seamus Fitzgerald's control of the Irish mob within San Fierro. His father, Patrick, had been inducted into life of crime while raising young Henry and caring for his wife whom he loved deeply. Upon loansharking for Fitzgerald, Patrick was shot and killed by an unknown hitman of an Italian crew in the Ocean Flats area. James, only the age of 4 years old was left with his mother. Growing up fatherless was a hard task for James, due to the jealousy of his friends with their fathers. Often he would be seen playing baseball in the street with fellow Irish-American children such as, Gerald Sullivan, and David Flanagan. Although he had no father a new figure appeared in James' life, Henry Fitzgerald. James would often sneak out late at night through his house window in order to climb down the storm drain and run off to Harold's bar. He'd serve drinks even though he was under aged and only about 12 or 13 years old at the time. The following year Henry Fitzgerald was also gunned down by suspected to be the same hitman that had killed James' father.


Young Irish-Americans playing in Bayside.


Young Callahan executing an associate of his.


After the death of Henry Fitzgerald and his father, James had been diagnosed with depression. Upon so, he thought of suicide several times in his late teens although not attempting it due to the thought of his friends and family. Though Fitzgerald was dead, many hoodlums of the neighborhood attempted keeping the mob tightly knit and together, no ranking structure, just a crime organization based off of respect. When James had his his late twenties he began working for the crew in the 60s. While doing so he had been deeply involved in crime with old friends such as Gerald and David. Running rackets together, the three were respected men among others. Not too long after many had looked up to the three and named them their leaders. James being the top dog, followed by Gerald, and David. Although they never had ranks he had named Gerald his "Right Hand" and David his "Enforcer". When becoming leader James felt it was necessary to clean out the mob of any rebellious young men. Upon doing so 17 murders were committed by the hands of the three men leading the mob. Several of the hits were done in the middle of the day, on the streets. Although the murders committed so openly, no one had testified to court due to the fact that they were deeply intimidated by Callahan and his associates. As no one would testify, James had felt very comfortable with his new position as a crime boss. He let the fact sink in that he was one of the most feared men in San Fierro. Although Callahan and Sullivan were untouched, was named a serial killer by cops. Yet no police department had any information on said murders. News companies had interviewed Flanagan several times where he had just ignored them completely. Upon this happening James was outraged and rumored to have car bombed a news van and hiring men to sabotage a helicopter used by the certain company. The three were crowned heroes by the criminals in San Fierro, although tensions with the Italians were still heated.

The 90sEdit

Aging with close friends Sullivan and Flanagan brought great honor to the three names. The fact that the three were there along with younger men to enforce the neighborhood with safety in exchange of extorting several businesses with the area had made neighbors feel secure in the area. No longer would anyone be taunted by other races or gunshots going off in the area hourly. The area had become somewhat peaceful with a twist of some organized crime within the area.