McCollum has been interested in trains from an early age, frequently riding the New York Subway for days at a time. His fixation with trains has led McCollum to frequently impersonate MTA employees or a related entity, for which he has been jailed numerous times. McCollum has been rejected for employment by MTA on numerous occasions, although he is reported to know more about the trains, schedules, procedures and rail operations than any current employee.
A prison psychiatrist who did an evaluation diagnosed him with Asperger syndrome. McCollum is said to have memorized the New York City Subway map by age 8.
It can be noted that Darius McCollum may have been inspired by the antics of Willie Henry Collins, known to the NYPD and Port Authority Officials as "Bus Willie", who was first arrested in 1973 for "borrowing" Greyhound and Trailways buses.
According to McCollum's mother, his interest with the New York City Subway system started in his youth, when subway motormen permitted him to drive trains. McCollum was first arrested in 1980, at age 15, when he drove an in-service New York City Subway E train for six stops. While he was in jail at Rikers Island, he wrote to the New York City Department of Correction and asked if he could drive one of their buses. By the mid-1990s, McCollum "had become a minor cult figure", particularly after the MTA posted thousands of wanted posters in trains and stations so that riders could report sightings. Occasionally, McCollum would appear as transit employees named "Morning" or "Manning", who riders invariably experienced as friendly and helpful.
By 2000, McCollum had been jailed 19 times for transit-related crimes. That year he pleaded guilty to charges of forgery and burglary for signing out a train according to proper MTA procedure to perform customary duties (extinguishing track fires, supervising maintenance), and then signing it back in. He was sentenced to a minimum of 2 1⁄2 to 5 years in prison. In 2005, McCollum was apprehended at a Long Island Rail Road yard with the keys to an M-7 railcar in his pocket. They had been given to him by his MTA friends who had given him their shifts, but he pleaded guilty to attempting to steal a locomotive and was sentenced to three years in prison. Although he was released from Sing Sing in 2006, he was reimprisoned for breaking parole after he was found in possession of railroad property.
On June 13, 2008, McCollum, now 43, was arrested again. He was wearing a hardhat and carrying a knapsack, flashlight and gloves with an MTA logo. He was dressed in the blue T-shirt and work pants typically worn by track workers and was arrested as he tried to enter a restricted area of a midtown station. McCollum was charged with criminal impersonation, criminal trespass and possession of burglary tools—a hammer and screwdriver tucked in his backpack. These "burglary tools" are also the typical repair equipment that all MTA maintenance workers carry. When his mother was interviewed over the telephone, she said, "Any time Darius wears anything remotely resembling the transit uniform, he gets arrested."
McCollum was released from the Downstate Correctional Facility on July 3, 2007—nine months after his arrest for violating parole by returning to the city from Winston-Salem, North Carolina. He was arrested at Penn Station on October 5, 2008, for impersonating a Long Island Rail Road employee and answering passengers' questions.
On August 31, 2010, McCollum was arrested for the 27th time and charged with grand larceny and possession of stolen property in connection with the theft of a private bus from a Trailways of New York terminal in Hoboken, New Jersey According to police, McCollum allegedly boarded the bus at approximately 6:30 a.m. that morning and discovered the keys left in the ignition. McCollum is accused of then commandeering the bus, with the theft reportedly going unnoticed for two hours as McCollum drove around John F. Kennedy International Airport and Jamaica, Queens. McCollum was taken into custody without incident. Police stated McCullom is "very smart, he's not a dumb guy" and that he was a "gentleman" during arrest and processing. At the time of his arrest, he had spent 18 years—more than a third of his life—in jail for transit-related offenses. In 2013, McCollum pleaded guilty to stealing the Trailways bus. On December 24 of that year, McCollum was released on parole and was to voluntarily enter cognitive behavioral therapy. The terms of the parole, which lasted until August 24, 2015, required that he does not operate a motor vehicle.
On November 11, 2015, McCollum was arrested for stealing a Greyhound bus from the Port Authority Bus Terminal in Manhattan. He drove the GPS-equipped bus for approximately 2 hours until his arrest at approximately 4 p.m. in Gowanus, Brooklyn. According to The New York Times, McCollum said, “I’m stealing a plane next” after his arrest.
Although his parents, who moved to Winston-Salem, North Carolina, believe McCollum should leave New York to avoid the temptation of the trains, parole conditions have until recently repeatedly restricted McCollum to remain in New York City. Suggestions from his parents and autism advocates that the MTA find a way to hire McCollum in some capacity, in the manner of Frank Abagnale, are rejected by transit officials, who fear legal liability and anti-disability stigma.
After McCollum used an insanity defense based on Asperger’s, he became a folk hero to people with Asperger diagnoses, especially children, celebrated for his “rebellion against what autistics often call the dreary world of the 'neurotypicals'”. In spite of his diagnosis from several psychiatrists, during at least two criminal proceedings, this defense was denied as the judge ruled he was “capable of controlling his impulses”.
A Harper’s Magazine article on McCollum by Jeff Tietz was a finalist in profile writing for the 2003 American Society of Magazine Editors awards. At the 2003 Edinburgh Fringe, Paperhat Productions of New York mounted a play by Director Jude Domski called Boy Steals Train, based on McCollum’s life and letters McCollum wrote to Domski, and described as “pointing a shaming collective finger at a judiciary that refuses to recognize Darius's condition”. The play was awarded a Fringe First by The Scotsman and the troupe won a Best Ensemble Acting Award. His story was also made into a BBC radio play, broadcast on BBC Radio 4 in August 2005.
McCollum appears in Episode 2 of “The Dark End of The Spectrum,” a two-hour, two-part, radio documentary that aired on CBC’s radio show Ideas on June 2, 2008 and again on July 24 (Part 1) and July 31 (Part 2), 2009.
A documentary film about McCollum, Off the Rails: The Darius McCollum Story, directed by Adam Irving, premiered on April 7, 2016 at the Full Frame Documentary Film Festival in Durham, North Carolina.