Fascinating handwritten letter (8.5x10.75") and matching envelope (4.13x9.38") from infamous gang leader, incarcerated Whitey Bulger. Contains many candid comments to Bulger's good friend concerning Bulger's criminal activities, his life on the run, and his troubles in prison. James "Whitey" Bulger was an Irish-American crime boss and FBI informant. He was the boss of the infamous Winter Hill Gang, from the Winston Hill district of Somerville, Massachusetts. According to the FBI, he started cooperating with the FBI in 1975, an allegation Bulger denied. In exchange for his status as a FBI informant, apparently the FBI overlooked many of the actions of Bulger's gang because Bulger was informing on his rival Patriarca Gang. When the media got wind of Bulger's criminal actions, Bulger disappeared for 16 years and was finally captured in Santa Monica, California, with his long term girlfriend Catherine Greig. This letter is to his old pal, Chris Duett, in Brockton, Massachusetts. Mailed from Plymouth County Correctional Facility in Plymouth, Massachusetts. Bulger discusses his deteriorating health and states, " ...came in here healthy, but isolation from people, little (being) up on feet, etc. is slowly wearing me down. Also affecting my mind - in time I give it a year, it's over. By then the family can accept it easier....But I'll never kill myself." Bulger also writes to his friend, "Want you to know - I never killed any women." Bulger also writes, "Any one who testified against me was given "deals" 14 years ago and lied. Bulger also states that when he was on the run, he and Catherine 'lived like normal elderly couple - went out for walks every day - never looking over shoulder. Live till you die - and that's the story." Bulger was killed by other inmates when he was transferred to the United States Penitentiary Hazelton, near Bruceton, West Virginia, in October 2018. The letter is written on lined paper with blue ballpoint pen and is neatly written. Closing and signature read. Sincerely, Jim Bulger. PSA authenticated and comes with an LOA.