Sean Hicks is a former Boston criminal and author who publicly ties himself to the Winter Hill Gang, claiming he is the nephew of co-founder Howie Winter and was recruited as a teenager by James “Whitey” Bulger. His criminal record is real and extensive, but the mob pedigree he built his memoir around has been rejected by former law enforcement officials and people who actually ran with Winter and Bulger.
Who Sean Hicks Is
Hicks grew up in South Boston and spent more than two decades in more than a dozen prisons, most of them maximum-security. He describes the neighborhood as offering a narrow set of futures: “priest, cop, or you became a crook.”1Telegram & Gazette. Sean Scott Hicks Seeks Redemption in Worcester While Sharing His Story By his own account he was running errands for a local mobster named Toby Rust at 10, drinking heavily by 15, and operating a small smuggling fleet out of a converted lobster boat by 16.2New York Post. How One Man Survived Life as a Boston Gangster
He published an autobiography, The Devil To Pay: A Mobster’s Road to Perdition, after Blackstone Publishing acquired worldwide rights in 2022.3Deadline. Blackstone Publishing Lands The Devil To Pay The book is the main vehicle for his Winter Hill claims.
What Hicks Says About the Winter Hill Gang
Hicks’s public identity rests on two assertions. The first is that he is the nephew of Howie Winter, who co-founded the Winter Hill Gang around 1961 in Somerville and led it until his 1979 arrest in a horse race-fixing case, the imprisonment that cleared the way for Bulger to take over.4Encyclopaedia Britannica. Winter Hill Gang5Boston Herald. Howie Winter Stops Into Sportsworld The second is that Bulger personally recruited him as a teenager to run jobs for the Irish mob.2New York Post. How One Man Survived Life as a Boston Gangster Hicks has restated both claims in interviews and across his memoir’s marketing.
Why Those Claims Are Disputed
A 2024 Boston Globe investigation reported that former law enforcement officials and former associates of Winter and Bulger rejected Hicks’s account of the relationship, calling the book a “fantasy” and Hicks “a complete fraud.”6Boston Globe. Sean Scott Hicks Memoir Whitey Bulger One former associate said, “Nobody in South Boston knows him. He’s lying about everything.”7CrimeWorld. Book Written by Alleged Whitey Bulger Irish Mob Insider Dubbed Work of Fantasy
The paper record also cuts against the family claim. Howie Winter died on November 12, 2020, at age 91 of a heart attack.8MassLive. Howie Winter, Former Winter Hill Gang Leader, Dies at Age 91 His obituary listed his wife, three daughters, grandchildren, great-grandchildren, nieces, and nephews, but did not name Sean Hicks.9Legacy.com / Boston Globe. Howard Winter Obituary The dispute between Hicks’s self-told story and the people who were actually inside the gang has not been resolved.
His Documented Criminal Record
Whatever the truth of the mob pedigree, Hicks’s rap sheet is not in question. Over his adult life he accumulated charges and convictions for conspiracy, racketeering, counterfeiting, money laundering, bank robbery, kidnapping, aggravated assault, and attempted murder.2New York Post. How One Man Survived Life as a Boston Gangster
In September 2000, Hicks was connected to the stabbing of Boston Celtics player Paul Pierce at the Buzz Club. He has said a music group he was associated with “got caught in the net that night” and that he violated parole through the association.1Telegram & Gazette. Sean Scott Hicks Seeks Redemption in Worcester While Sharing His Story MassLive reported he served 10 years in connection with the incident.10MassLive. Nephew of Winter Hill Gang Founder Finds New Direction in Worcester
In 2011 he was involved in what he called a “territorial dispute” in South Boston, which MassLive described as a shooting between two rival gang members. He was charged with attempted murder and aggravated assault, served about five years, and was released from the Massachusetts Correctional Institution at Cedar Junction in early 2016. Cedar Junction officials cited his “long-standing associations to organized crime” as the reason for keeping him in maximum security, and facility records indicated he was accused of a “racially-toned” stabbing while incarcerated.10MassLive. Nephew of Winter Hill Gang Founder Finds New Direction in Worcester In his memoir, Hicks wrote that he helped smuggle heroin, cocaine, and marijuana into prison, and that he drank through his sentences while enrolled in rehabilitation programs meant to reduce them.2New York Post. How One Man Survived Life as a Boston Gangster
After the 2016 release he violated parole and was sent to the Worcester County House of Correction for roughly another year. His final release came in 2020.1Telegram & Gazette. Sean Scott Hicks Seeks Redemption in Worcester While Sharing His Story2New York Post. How One Man Survived Life as a Boston Gangster
The Gardner Museum Allegation
Hicks’s name has also surfaced in connection with the unsolved 1990 Isabella Stewart Gardner Museum heist, the largest art theft in history. Records from MCI-Cedar Junction obtained by MassLive indicated that Bulger named Hicks and Howie Winter as suspects in the robbery. Hicks has said he was never questioned by investigators and dismissed Bulger as a career informant, saying he had “been ratting people out since the ’50s.”10MassLive. Nephew of Winter Hill Gang Founder Finds New Direction in Worcester The Boston Globe reported that former law enforcement officials also refuted the connection. The heist remains unsolved.6Boston Globe. Sean Scott Hicks Memoir Whitey Bulger
Where Hicks Is Now
Since his 2020 release Hicks has lived in Worcester, Massachusetts, where he runs a construction business and works in real estate development. He performs hip-hop under the name “Ghost,” a nickname he says he picked up during two years as a fugitive, and co-founded Mob Rock Records in 2021, which secured distribution through The Orchard, a Sony Entertainment subsidiary.3Deadline. Blackstone Publishing Lands The Devil To Pay As of 2022 he was filming an unscripted television series about his post-prison life, produced by Aaron Semmel; no information has surfaced about the series being completed or aired.11Deadline. Blackstone Lands The Devil To Pay
He has spoken openly about mental health and addiction, saying he has been diagnosed with borderline antisocial personality disorder and PTSD and used alcohol to cope for decades. His sobriety began at the Worcester County House of Correction through a substance abuse program, and in a 2021 interview he reported roughly 18 months sober while attending counseling, addiction treatment, and court-ordered anger management. He has framed his public story as a cautionary example for at-risk youth: “Rehabilitation is possible. Life is like a book and this is one chapter.”1Telegram & Gazette. Sean Scott Hicks Seeks Redemption in Worcester While Sharing His Story