Why Did Whitey Bulger Go To Alcatraz? 'Black Mass' Hints At The Gangster's Stay At The Infamous Prison

Black Mass has the difficult duty of packaging the highlights (or lowlights, as it were) of the life of notorious organized crime boss Whitey Bulger into a feature-length film. In the decades that Bulger was active in racketeering, drug running, and his other bad-guy pastimes, a lot went down that the Johnny Depp movie doesn't have time to touch on. The main focus of the narrative is the "devil's deal" between the gangster and the FBI; details of his life that aren't relevant to that understandably are glossed over. Among those details is Bulger's stint in the Alcatraz, the world-famous maximum-security prison that sits in the San Francisco Bay, which is mentioned but not explored. So, why did Whitey Bulger go to Alcatraz, and when did it happen?

Bulger served four years of time in Alcatraz beginning in 1959. The career criminal was 30 when he was transferred to that prison, though the time he spent there was only part of a nine-year sentence. The crimes that predicated this incarceration were several counts of hijacking and armed robbery. After his trial, Bulger was first sent to the Atlanta Penitentiary where he was a part of the CIA-sponsored MK-ULTRA program that used inmates as guinea pigs to test the effects of LSD and similar hallucinogens. The men volunteered for the study, but some allege that they were misled as to what they were really signing up for and how their participation would be recognized.

After authorities learned that he was planning an escape from that institution, Bulger was transferred to Alcatraz. CNN interviewed self-proclaimed Alcatraz historian Michael Esslinger, who has written two books on the defunct correctional facility — Letters From Alcatraz and Alcatraz: A Definitive History Of The Penitentiary Years — about his correspondence with Bulger on the topic. The author estimated that he received over 1,000 pages of handwritten letters from the gangster, and many of those include nostalgic words about his time there. He even missed the view, which he described to Esslinger as "the best view from any prison in the world."

If I could choose my epitaph on my tombstone, it would be: "I'd rather be in Alcatraz. 1428AZ." [His inmate number] All that remains on Alcatraz today are our ghosts.

Whitey Bulger and his fellow Alcatraz inmates were a "band of brothers," Esslinger wrote. The gangster forged a particularly strong friendship with a young Native American man named Clarence Carnes and treasured that relationship so much that he ordered Carnes's body exhumed and re-interned on Choctaw burial ground. He also foot the bill.

In 1962, Bulger was transferred again, and eventually released on parole in 1965. But he always remembered his years at Alcatraz fondly. The proof is in a fairly unbelievable photo of Bulger and then-girlfriend Teresa Stanley playing tourists at the prison in 1995. Clad in borrowed black-and-white, the pair smile for the camera at the site where Bulger's quarters were barely wide enough to raise his arms and his days were spent laundering uniforms for the Navy. The shot is a visual example of Bulger's strange detachment from his own crimes, and everything that makes him a fascinating subject for a film.

Image: Warner Bros. Pictures