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Don't Talk About Joe Mac
The Life, Wars, and Secret History of the Man Behind the Winter Hill Gang
Don't Talk About Joe Mac
The Life, Wars, and Secret History of the Man Behind the Winter Hill Gang
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Description
Forget what you think you know about the Winter Hill Gang; this, at long last, is the ruthless truth of the Boston underworld and most ominous figure - his tragic origins, unsolved murders, and his daughter who broke the silence around him.
In 2020, author Springs Toledo set out to find a ghost in the Boston underworld whose name can end a conversation - what he found is startling. Don't Talk About Joe Mac is a true crime biography that reads like noir fiction. It is a journey through a shadow society as bizarre as it was impenetrable; an exposé that will upend the official narrative animating United States v. James J. Bulger (2013) as it corrects the record and takes the top off a succession of unsolved murders.
Joe McDonald (1917-1997), a World War II veteran and father of five, was the most revered career criminal in the region and its most prolific killer. He founded the Winter Hill Gang in the 1950s, became the bogeyman of the infamous Gangland War of the 1960s, and was among the FBI's Ten Most Wanted Fugitives in the 1970s, and yet his name was barely mentioned and his exploits only whispers.
His daughter, whose own unforgettable story is laced within his, brings us uncomfortably close to a personality marred by trauma. This is Joe Mac's story, a story you were never supposed to know.
Table of Contents
Part I: The Descent
Chapter 1: August 9, 1942
Chapter 2: Dear Ma
Chapter 3: Joe Noir
Chapter 4: A Pillow of Stone
Chapter 5: The Box
Part II: The Gangland War, 1961–1966
Chapter 6: “The Go-to Place for Summer Fun”
Chapter 7: “Boston Was Overrun With Sick Bastards”
Chapter 8: “Wait for the Splash!”
Chapter 9: “Buddy Was My Best Friend”
Part III: 1966–1973
Chapter 10: Walpole-28333
Chapter 11: The Friends of Kathy Murphy
Chapter 12: Crimson and Clover
Chapter 13: Blue Sunday
Chapter 14: The Man Who Wouldn't Die
Chapter 15: Chandler's
Chapter 16: Howie Winter's Mistake
Chapter 17: Blurred Lines
Part IV: 1973–1975
Chapter 18: Behind Closed Doors
Chapter 19: What Happened to John Leary
Chapter 20: Whitey and the Hit Squad: the Real Story
Part V: 1975–1983
Chapter 21: Jim Sims
Chapter 22: The Murder of Raymond Lundgren, and Then Some
Chapter 23: Two Fugitives in Florida
Chapter 24: Truth, Lies, and World Jai Alai
Chapter 25: “Because I'm Queer”
Chapter 26: Whitey Bulger v Joe Mac
Part VI: 1987–1997
Chapter 27: Pandemonium Day
Chapter 28: The Disappearance of Jim Sims
Chapter 29: Quincy
Chapter 30: 41
Epilogue: Jackie, Today
Acknowledgments
Bibliography
Index
About the Author
Product details

Published | 19 Mar 2026 |
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Format | Hardback |
Edition | 1st |
Extent | 352 |
ISBN | 9798881842499 |
Imprint | Bloomsbury Academic |
Illustrations | 26 bw photos |
Dimensions | 229 x 152 mm |
Publisher | Bloomsbury Publishing |
About the contributors
Reviews
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I always avidly await another book by Springs Toledo. I can count on him to explore dark and dangerous places, and trust that his heart and humanity will make it a trip worth taking. Don't Talk About Joe Mac is beautiful-the way a perfectly thrown left hook is beautiful.
Eddie Muller, “The Czar of Noir,” TCM's host of Noir Alley TV series, founder and president of The Film Noir Foundation, and producer and host of Noir City: The San Francisco Film Noir Festival
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Toledo's book is a revelation-for the quality of its investigation and the humanity with which it lays bare the life of a decorated World War II veteran, a husband and father, a gangster and prolific professional hit man. Joe McDonald is likely a name unknown outside the mean streets of the Boston underworld, but after reading Don't Talk About Joe Mac, you will feel as though you know the man. Toledo has peeled back the onion to reveal the beating heart of a sentimental, old-school tough guy who killed people for a living. Brutal, masterfully written, unrelenting in its excavation of fresh information, and with startling disclosures, this book may be the best portrait of a certain type of twentieth century American street mobster ever to appear in print. Get this book now.
T.J. English, New York Times bestselling author of The Westies, Havana Nocturne, and Where the Bodies Were Buried
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Don't Talk About Joe Mac may well be the last of the great Boston Mob books. Springs Toledo delivers the whole package on the enigmatic Winter Hill boss-fine writing, familial insights from his daughter and many memorable stories. And he solves the mystery of the 1992 disappearance of Jimmy Sims, Joe Mac's partner in crime. A must-read for all Boston OC aficionados!
Howie Carr, New England's undisputed talk radio king, New York Times best-selling author of The Brothers Bulger and Hitman, and columnist for the Boston Herald
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Whatever Springs Toledo writes I want to read. He's that kind of a writer.
Robert Atwan, editor of numerous literary anthologies and series editor of The Best American Essays (1986 – 2023)
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Springs Toledo has crafted a masterpiece-a window into the machinations of Boston's gangster class, a window revealing treachery, bloody betrayals, murders, and “disappearances.” At its center is Joe McDonald, a prolific killer and master of disguise whose deadly business is unheralded-by choice. His sources are outright amazing. If the opening doesn't grab you, check to see if you have a pulse.
In 40 years of reporting true crime, organized and otherwise, never have I read a book like this.Ron Gollobin, Pulitzer-nominated investigative journalist, five-time Emmy award-winning investigative reporter, and crime reporter at WCVB-TV (Boston), 1975-1999
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Springs Toledo's research would have been invaluable in our murder investigation of Roger Wheeler in Tulsa, Oklahoma, in 1981; his information is so detailed and complete it is obvious he had inside sources.
Mike Huff, former Detective Sergeant, Tulsa Homicide Unit, and lead detective on the decades-long World Jai Alai investigation