A main character in Carla Conti's book Chained Birds: A Crimemoir, befriends famed Boston crime boss Whitey Bulger in the Florida prison where the two men served for four years before Bulger was murdered behind bars.

A main character in Carla Conti's book Chained Birds: A Crimemoir, befriends famed Boston crime boss Whitey Bulger in the Florida prison where the two men served for four years before Bulger was murdered behind bars.

In 2014, inmate Kevin Sanders stepped off a ConAir flight from Pennsylvania to a tarmac in Orlando, where he met an “old timer” similarly dressed in an orange jumpsuit and belly chain. The ornery felon with a sharp tongue and Southie Boston accent turned out to be the notorious Boston mobster Whitey Bulger. Kevin and Whitey were slated for the same prison bus going to the same federal penitentiary, and that moment sparked a friendship between the two convicts that lasted for four years — right up to Whitey’s transfer and murder in a West Virginia medical prison in 2018.

Whitey is by no means a central character in my upcoming book Chained Birds: A Crimemoir, but he does appear in four chapters as a confident and fellow convict to one of my main characters, inmate Kevin Sanders. Why do I mention this here and across my social platform? Because it’s freaking fascinating, right? That there are new Whitey Bulger stories that no one else has heard of — until my book is published — is worth touting. It’s also one of my main hooks to get Chained Birds: A Crimemoir on the radar of lit agents and editors as I tread the yellow brick road into traditional publishing. Go ahead and judge, but it’s a cutthroat world out there (like it is in prison), and a girl’s gotta do what a girl’s gotta do to get noticed and survive.

Whitey Bulger Alcatraz 1959 Mugshots - Wikimedia Commons
Whitey Bulger claims he was given LSD as an “experiment” while at Alcatraz Prison, inducing lifelong night terrors (Whitey Bulger Alcatraz 1959 Mugshots – Wikimedia Commons)

Some teasers about Whitey in my upcoming book include:

  • How Kevin and Whitey sized each other up on the hour-long bus ride, with Kevin teaching Whitey how to escape their belly chains and Kevin offering his friendship and “assistance” at their new facility.
  • How Whitey described being given LSD as an “experiment” in his early days of incarceration at Alcatraz Prison, which left him with lifelong night terrors and the inability to sleep without a light on.
  • How Whitey described his years on the run with girlfriend Catherine Greig and begged Boston prosecutors to give her a more lenient sentence in exchange for his death penalty.

Let me be clear: even in his old age and locked up after 16 years on the lam, Whitey Bulger stirs no sympathy. It’s not my intention to glorify a vicious mobster who was finally convicted of multiple murders. I do, however, portray Whitey the way his fellow inmate Kevin Sanders saw and interacted with him … proving once again the adage that truth really is stranger than fiction.

**Photo credits in feature image:
Whitey Bulger 1953 Mug Shots – Boston Police via Boston Globe
Whitey Bulger 2011 Mug Shots – US Marshals Service
Whitey Bulger 2011 custody transport photo credit – Stuart Cahill/The Boston Herald, via Associated Press

Carla Conti is a true crime journalist, storyteller, and prison reform advocate. Look for Chained Birds: A Crimemoir, her true crime memoir and exposé on federal prison abuse, corruption, and prison gang culture in 2024.

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