Chapman’s first felony conviction came days before his 18th birthday in November 1993. Chapman and an accomplice pleaded guilty to a pair of felony robbery charges, according to Texas court records.
Chapman, Houston police charged, pointed a firearm at two victims and demanded money. Though he was only brandishing a pellet gun, Chapman warned, “This is a .44 Magnum. Give me your money or I will shoot you.”
During a 2009 prison evaluation, Chapman told a psychologist that he had been “booted out” of high school “due to disciplinary problems.” Chapman said he joined the Navy in 1993, but never served due to the robbery arrest. He also told the prison doctor that, as a juvenile, he abused alcohol and used LSD and marijuana. But his "substance of choice," Chapman added, was Scotchgard fabric spray, which he huffed.
Sentenced to five years in prison, Chapman served a combined 30 months in custody before being paroled in 1996. During his incarceration, Chapman said, he was repeatedly assaulted by fellow inmates.
Chapman eventually moved to California, where he worked as a bouncer at various San Diego-area strip clubs. During his 2009 psych exam, Chapman said that he stopped drinking while on parole in Texas, but resumed imbibing in California.
Chapman’s next felony conviction came in June 2001, when he pleaded guilty to grand theft. According to Superior Court records, he stole in excess of $400 worth of merchandise from a Macy’s in San Diego. Chapman was sentenced to four years in prison--three years on the grand theft rap and a one-year “enhancement” due to his prior conviction for robbery.
Chapman served a total of two-and-a-half years in custody, according to California court and corrections records. He was twice sent back to prison for violating terms of his parole, resulting in an additional five months behind bars.
After his release from prison, Chapman was under psychiatric care and was prescribed multiple medications for depression and anxiety. When his parole term expired, Chapman later told a psychologist, he “stopped all medication.” But he continued to drink heavily and was abusing the painkiller Vicodin (taking upwards of 30 pills daily). Chapman also acknowledged smoking pot and using cocaine “once in a while.” [The psych report notes that Chapman used methamphetamine as an adult, but it does not specify a time frame.]
Chapman’s most recent felony conviction came as a result of an undercover operation launched by Bureau of Alcohol, Tobacco, Firearms and Explosives agents and the San Diego Police Department’s street gang unit.
With the help of a confidential informant, investigators determined that an owner of a San Diego tattoo shop was illegally selling guns from the business. Agents suspected that some of the weapons ended up in the hands of local Hispanic street gang members.
On two occasions, Chapman provided the tattoo shop owner with weapons--a shotgun and an assault rifle--that were then immediately resold to the informant. One evening, as Chapman drove from his home to the tattoo shop to deliver the assault rifle, a San Diego Police Department surveillance helicopter followed Chapman's Lexus on the six-mile trip.
Chapman was named in a July 2008 indictment charging him with two counts of being a felon in possession of a firearm. Chapman was arrested at his San Diego home, which was simultaneously searched by cops and ATF agents. According to a search warrant inventory, investigators seized body armor, a Ruger pistol, two throwing knives, a bag of "suspected marijuana," metal knuckles, two glass pipes, assorted ammo and shotgun shells, clips, and magazines.
In a plea agreement, Chapman copped to the felony charge related to his possession of the assault weapon.
While free on $35,000 bond posted by his girlfriend (who is now his wife), Chapman went on the lam before his February 2009 sentencing. During his one month as a fugitive, Chapman was “living as a homeless person in river beds,” according to a court filing by his lawyer, who claimed that his client “has severe psychological problems” and suffered from auditory and visual hallucinations and “delusions of persecution.”
After Chapman surrendered to federal agents, a U.S. District Court judge ordered a psychological evaluation to determine whether the felon was “suffering from a mental disease.” A Bureau of Prisons psychologist subsequently concluded that Chapman was not “substantially impaired by a mental disease or defect” and had not exhibited “any symptoms of serious mental illness” while being held in San Diego’s Metropolitan Correctional Center. Regarding a personality test that purported to show that Chapman was “psychologically disturbed,” Dr. Gordon Zilberman found that Chapman likely was “exaggerating or manufacturing symptoms when completing this test.”
In June 2009, Chapman was sentenced to 63 months in federal prison to be followed by a three-year probation term. Among the character references sent to the judge by Chapman’s family and friends was a letter from Chapman’s brother Derek. Sent a day before Chapman became a fugitive, the letter described the defendant as a “generally law abiding person.” Jeff Kugel, who met Chapman in 2007, wrote that “Kyle is very knowledgeable about history and the struggles of mankind against central power structures.” Kugel added that, “It is easy to come across as a little paranoid to the uninitiated when broaching this subject.”
After five years behind bars, Chapman was released from Bureau of Prisons custody in January 2014, at which time his probation sentence began. The terms of his supervised release included periodic drug testing and substance abuse treatment. He was also barred from consuming alcohol, attending gun shows, and possessing body armor, firearms, and ammunition. Chapman was also directed to participate in a mental health treatment program as directed by his probation officer.
Chapman’s federal supervision ended less than two months before the shield-carrying “Alt-Knight” made his March debut on the Berkeley streets. Court records contain no indication that Chapman’s federal probation was violated at any time.