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Legends of Winter Hill: Cops, Con Men, and Joe McCain, the Last Real Detective

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“At McCain Investigations, I’d be sent looking for people who didn’t want to be found, following guys who didn’t want to be followed, and entering neighborhoods where I was not at all welcome. There would be no commercials, no time-outs, no ‘do-overs’ if somebody got shot or stabbed or run over. These guys were playing for keeps.”

Seasoned journalist and adventurer Jay Atkinson spent a year working as a rookie private eye for the storied firm McCain Investigations, founded by the late Joe McCain, Sr., one of the most decorated police officers in Boston history. In his colorful narrative style, Atkinson describes some of the cases he worked as a detective, chasing down an assortment of felons, thieves, and con artists, as well as the ghost of a real-life American hero, legendary cop Joe McCain.

Atkinson traces McCain’s story from the day he put on his Boston Metropolitan Police uniform in the 1950s through the heyday of his run-ins with mafiosi, bad cops, and ruthless killers. Big Joe was the genuine article, a detective so committed to his work that a gunshot wound suffered in the line of duty took thirteen years to kill him. McCain pursued such infamous Winter Hill mobsters as Stephen “the Rifleman” Flemmi and the murderous James “Whitey” Bulger, who remains on the FBI’s Ten Most Wanted list. Here Atkinson reveals new details—based on his exclusive interviews and an abundance of his own shoe leather—about how Bulger, one of America’s most notorious fugitives, came within inches of being apprehended during Joe McCain’s reign.

Atkinson also tracks the career of Joe McCain’s son, Joe Jr., a tattooed, hard-riding motorcycle fanatic who followed his old man onto the force. Since big Joe’s death, young Joe has learned the hard way that a father’s mythic persona can be both a blessing and a curse, as a fellow cop with a grudge against Joe Sr. may be out to ruin young Joe’s career. Atkinson delves into this dark and dangerous aspect of “the job,” where it’s uncertain which side some cops are on.

Legends of Winter Hill takes you into an alluring and gritty world where heroes go unsung every day, and moral boundaries aren’t always black and white.


From the Hardcover edition.

368 pages, Hardcover

First published January 1, 2005

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Jay Atkinson

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5 stars
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Displaying 1 - 8 of 8 reviews
Profile Image for Mia Parviainen.
121 reviews11 followers
July 23, 2013
"Legends of Winter Hill" is a complex book that follows multiple threads. Author Jay Atkinson focuses on Joe McCain, a celebrated Boston-area detective. The book follows McCain's career as a law enforcement officer and founder of private investigation firm. During other passages, Atkinson writes about McCain's legacy, including McCain's son who also enters law enforcement. For another layer of story, Atkinson himself decides to try out private investigating, following McCain's son and associates on various cases.

The anecdotes and stories shared range from funny to shocking. The faint of heart might not fare well--the language used by figures in the book are seldom censored. Additionally, some of the incidents related are graphic. The book brings up a host of questions about separating black and white, or trying to stay on the side of "good." McCain is depicted as an honorable man, though some try to smear his reputation.

At times, the density of the details provided makes for tricky reading. More than once, I had to go back and reread a passage to figure out what exactly was going on. Ideally, the book should be read with a chart of characters--there are many to keep track of, from all of the different threads in the book. At the same time, there isn't really a linear narrative. The book jumps around in time. McCain's early life is addressed, and his death is depicted in the end. In between, the time jumps around frequently. It makes for brisk reading, but reading that really can't be rushed.

Bottom line: entertaining for Boston-area natives & aficionados, thought-provoking for those who wonder about the line between good and evil, and horrifying for those with weak stomachs.
Profile Image for CJ.
156 reviews14 followers
August 6, 2016
The loose framework of the book involves author Jay Atkinson spending a year working at a Boston detective agency founded by detective Joe McCain and run by his son. During the course of his work he learns about the criminal element of old Boston (the Winter Hill neighborhood in particular) and about Joe McCain's success as a police officer and detective keeping his streets safe. There are many colorful anecdotes about Officer McCain's experiences dealing with Irish mob kingpins and low-level con men alike, as well as fighting corruption within the police department.

On the whole, it's a good book, although it's extremely episodic and frankly a bit jumbled for my taste--there is no organization to the tales as far as I could tell, which often left me confused about when events had occurred. The character of Big Joe was well drawn, Atkinson letting the people who knew the man best tell us about him in their own words. I think the book could have been tighter and include more real information--it seems as though a lot of times the author relies on secondhand stories without doing any real primary source research. However, on the whole I would recommend it to people who enjoy police stories or are interested in the Winter Hill neighborhood.
Profile Image for Janellyn51.
884 reviews23 followers
April 5, 2022
I was visiting my Uncle Sonny, a former MDC or Met Cop, in Florida a few years ago. I said something about living in Somerville, and he almost choked! He said, I thought you lived in Cambridge, Jesus Christ, you know what we used to say about Somerville......put a fence around it and give em all 10 to 20!!! My Uncle was mounted police in Hull by Nantasket where there was an amusement park by the sea. That's South Shore. Joe McCain and Leo Papile were in Revere, that also had an old Amusement park, it's North Shore. I'm not sure that Atkinson gets across just how sleazy those clubs along the drive in Revere are, or how many of them are left. At some point my Uncle was also mounted MDC in the Blue Hills where he found a body that was a mob hit, I'm not sure who.
I mostly read this because I think it's important to know who you're talking to. Like, for example, my chucklehead brother was a bartender in Falmouth. He calls me up and tells me two guys from Somerville were in the bar. When he heard that, he says my sistah lives in Somerville. Who's he talking to? Leo Martini, and Johnny Martorano of all people. Leo is a great guy, was a good cop, so fine, but fucking Johnny Martorano? Leo asked him what my number is and he'll check up on me! I ran into him and said I hear you met my brother, and sure enough, he took a card out of his wallet and there it was!
Anyway. I would have given the book more than 3 stars, but it does jump all over the place, and it's kind of hard to follow what happened when. The corruption is way way out of control. Curtatone the mayor he talks about Who's cousin was dealing in the high school, is so oily he could slide under a door, he's out now.....but ding dong , he's had a lot of balls talking about addressing the opioid crisis.
I wish I had met Big Joe McCain, he sounds like quite a man.
Profile Image for Maura Mann.
74 reviews6 followers
March 23, 2021
As a Bostonian, the idea of this book is great. True crime but not all about Whitey Bulger. Joe McCain led an interesting and impactful life and I enjoyed reading some of the stores about him. That said, I don’t think this book was arranged well. It was extremely hard to follow and jumped all over the place. I had a hard time figuring out when things took place. I think the story would have been told better in some type of chronological order.
Profile Image for Summer.
298 reviews165 followers
April 2, 2008
I wanted to like this more, because gosh! A Goodfellas-style drama going on in my own backyard, for real! This book kind of jumped around, though - it seemed more suited to being several short articles than one huge narrative. Interesting subject matter, though.
1 review2 followers
August 20, 2009
Great true crime story from an absolutely engaging writer.
215 reviews
July 4, 2016
More of a collection of fact (or fiction depending on your view) vs novel.
Displaying 1 - 8 of 8 reviews

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