James Joseph Bulger, Jr was born September 3, 1929, to James Joseph and Jane Veronica “Jean” Bulger. He was their first of three children. His father hailed from Newfoundland. The senior Bulger’s parents had both been Irish. Jean was a first-generation Irish immigrant. The younger Bulger’s blood ran green.

James Senior worked as a longshoreman but lost his arm in an industrial accident. There were not quite so many lawyers back then as is the case today. Though the man survived, his family was left destitute. They moved into the Mary Ellen McCormack housing project in South Boston in 1938.

James had two younger brothers, both of whom did well in school. By contrast, James Bulger Jr seemed drawn to the streets at a young age. The kid was a born thug.

To his friends, James went by “Jim”, “Jimmy”, or “Boots.” The latter appellation stemmed from his tendency to wear cowboy boots in which he hid his switchblade knife. When he was young the kid’s hair was blonde to the point of being white. As a result, his chums took to calling him “Whitey.” Though the young man despised the nickname, it nonetheless stuck.

Whitey Bulger’s first arrest was at age 14 for larceny. He ran with a South Boston street gang called the Shamrocks. While with this crew Bulger was eventually arrested for assault, forgery, and armed robbery. He spent time in the juvenile reformatory, but everybody wants kids to succeed. Soon after his release in 1948, Whitey was allowed to join the US Air Force in hopes that a little time in uniform might straighten him out.

Airman Bulger did not thrive in the service. He spent time in a military prison for multiple assaults and also went AWOL. By 1952 Uncle Sam had given up on Whitey and sent him packing, albeit with an honorable discharge. Four years later Bulger was remanded to federal prison for armed robbery and hijacking. Apparently, the kid just couldn’t help it.

As we mentioned earlier, this was a different time with very different rules. While serving time in prison Bulger was used as a test subject for the CIA’s Project MK-ULTRA. This enterprise was pitched as an effort to cure schizophrenia. In reality, the CIA was trying to develop a mind control drug. While Bulger and the eighteen other participants in the program had indeed volunteered in exchange for reduced sentences, they had no idea of the true nature of the program. They received heavy doses of LSD along with several other hallucinogens. Bulger later admitted that the experience was horrifying. He began hearing voices afterward as a result.

Bulger was later transferred from Atlanta to Alcatraz and then on to Leavenworth. In 1963 he was sent to Lewisburg Federal Penitentiary. On his third try, Whitey Bulger was paroled in 1965. He had served a total of nine years. The career criminal would not see the inside of a prison again for another nearly half-century. However, that wasn’t for lack of trying.

As an ex-con, solid work was tough to find. Bulger toiled as a janitor and construction worker before returning to the only thing he had ever been good at. Under a mob boss named Donald Killeen, Whitey Bulger began working as a loan shark and bookmaker. The Killeen Gang had been a fixture in South Boston for more than two decades.

The Killeen Gang was led by three brothers—Donnie, Eddie, and Kenny. Kenny Killeen purportedly shot and injured Michael “Mickey” Dwyer, a player in the rival Mullen Gang, during a fight at the café the Killeens used as a headquarters. There resulted a sprawling gang war that swept across Boston stacking up quite the body count. The Killeens soon found themselves outgunned by the younger, more agile Mullens mob. As part of this fight, Whitey was dispatched to liquidate a Mullens Gang member named Paul McGonagle. In a tragic case of mistaken identity, Whitey accidentally killed Paul’s fraternal twin brother Donald. This was Whitey Bulger’s first proper murder. It would not be his last.

One of the players named Kevin Weeks later said, “Although [McGonagle] never did anything, he kept on stirring everything up with his mouth. So (Whitey) decided to kill him…(Whitey) shot him right between the eyes. Only…it wasn’t Paulie. It was Donald…(Whitey) drove straight to his mentor Billy O’Sullivan’s house (who was cooking at the stove top at the time)…and told O’Sullivan…’I shot the wrong one. I shot Donald.’ Billy…said, ‘Don’t worry about it. He wasn’t healthy anyway. He smoked. He would have gotten lung cancer. How do you want your pork chops?”

Sensing that time was running out on the Killeens, Bulger supposedly approached Howie Winter, another mob boss who led the Winter Hill Gang, and offered to end the war. In May of 1972, the eldest Killeen was gunned down outside his home. While there remains some controversy, Bulger was rumored to have been the triggerman. The remnants of both the Killeen and Mullens gangs were subsequently absorbed into the Winter Hill mob.

Bulger was a cold-hearted murderer, but he was also smart. In this chaotic world, his steady leadership and ruthless demeanor brought him great success. Kevin Weeks also had this to say, “As a criminal, he made a point of only preying upon criminals…And when things couldn’t be worked out to his satisfaction with these people, after all the other options had been explored, he wouldn’t hesitate to use violence…Tommy King, in 1975, was one example…Tommy, who was a Mullens, made a fist…(Whitey) saw it…A week later, Tommy was dead. Tommy’s second and last mistake had been getting into the car with (Whitey), Stevie, and Johnny Martorano…Later that same night, (Whitey) killed Buddy Leonard and left him in Tommy’s car on Pilsudski Way in the Old Colony projects to confuse the authorities.”

Whitey’s allegiances shifted with the winds to his maximum advantage. Along the way, he worked as an informant for the FBI while continuing his overt criminal enterprise. In September of 2006, federal judge Reginald Lindsey ruled that the FBI’s botched management of Bulger as an informant had contributed materially to the 1984 death of a government snitch named John McIntyre. The judge awarded McIntyre’s family $3.1 million in damages as a result.

In 1982 Bulger and an associate approached a well-known local cocaine dealer with the street name of “Balloonhead” while he was traveling in a car with a friend. Bulger packed an M1 carbine, while his fellow hitter was armed with a full auto sound-suppressed MAC-10. The two men liberally sprayed the coke dealer’s vehicle at close range. Balloonhead and his buddy died on the spot.

Whitey thrived throughout by threatening and killing competitors and turned enormous profits through his sundry criminal enterprises. It was estimated that he made some $30 million solely by charging local drug dealers fees for operating on his turf. Bulger and his buddies also shipped, “91 rifles, 8 submachine guns, 13 shotguns, 51 handguns, 11 bullet-proof vests, 70,000 rounds of ammunition, plus an array of hand grenades and rocket heads,” along with substantial quantities of C4 plastic explosive to IRA terrorists in Northern Ireland.

With the Law Enforcement heat becoming unbearable, Bulger fled Boston in 1995. He traveled widely in the US and Europe before finally being arrested in Santa Monica, California, in 2011 at age 81. He had been on the run for sixteen years and had been on the FBI’s Ten Most Wanted Fugitives list for twelve of those. The details of those years as a fugitive would require another couple of columns to fully explore. At the time of his arrest, Bulger had 30 firearms, several fake IDs, and $800,000 in cash in his apartment.

What spawned this project was a photograph of Bulger’s arsenal that was released after his capture. Bulger apparently had an affinity for 1911 pistols as there were several in attendance. He also had half a dozen fully automatic weapons. Dissecting his arsenal lends insight into the man and the brutal nature of his crimes.

Bulger’s handguns included a Walther P38, a Ruger .22 pistol, and a variety of revolvers. In addition to his weapons, police seized Law Enforcement badges and assorted carry gear along with fighting knives. However, it was the machine guns that were the most fascinating.

Bulger had a .45ACP MAC M-10 with an original WerBell-designed two-stage sound suppressor. There was also an M1 carbine with a civilian sliding “paratrooper” stock. His SP1-style AR15 included the original 20-inch rifle barrel and triangular handguards but had been fitted with a collapsible CAR-15 buttstock.

Whitey had a fascinating M3 Grease Gun that appeared to include an original GI OSS sound suppressor. These customized Grease Guns were some of the first operational sound-suppressed SMGs to see service alongside the Mk IIS suppressed Sten. We can only imagine where that particular weapon had been. The stash also included three well-worn 9mm German MP40 submachine guns.

Bulger was convicted in short order. He had been charged with a total of nineteen different murders. His first prison stop was the US Penitentiary in Tucson. Soon after his arrival a fellow prisoner nicknamed “Retro” stabbed the elderly criminal in the head and neck with a homemade knife, putting him in the prison infirmary for a month.

Bulger was subsequently moved to the US Penitentiary in Hazelton, West Virginia, on October 29, 2018. By this point, he was wheelchair-bound. The following day Whitey Bulger was beaten to death by multiple inmates armed with a padlock wrapped in a sock and a homemade blade. His eyes were all but gouged out and his tongue was nearly severed. In August of 2022 three inmates named Paul DeCologero, Sean McKinnon, and Fotios Geas were indicted for Bulger’s death. Their cases are winding through the legal system as I type these words.