Uncle Tommy, Red Shea and the Winter Hill Gang

Bolando reviews the top Whitey Bulger books on the market including one where his Uncle Tommy is in. My question is when can we expect Uncle Tommy to make an appearance in the Bingo Bar??? Enjoy...

Since the first book on Whitey Bulger came out, Black Mass, there have been a series of books approaching the story from different angles. Last I checked, there have been at least 5 different books. So far I've read 4 of them - "Black Mass," "Street Soldier," "Rat Bastards" and "The Brothers Bulger." I have "Brutal" on my bookshelf and I really don't know when I'll get to it. Having just finished two of them recently, I'll probably look for a new topic to read. The following is a multi-part series on my reviews of the various books.


The current rankings on the books are as follows:

1 - Brothers Bulger - by Howie Carr

2 - Black Mass - by Dick Lehr

3 - Rat Bastards - by John "Red" Shea

4 - Street Soldier - by Eddie Mackenzie



It's difficult to really compare all of them because 2 are written by investigaters (Brothers Bulger & Black Mass) and 2 are written by actual role players in Whitey's underworld (Rat Bastards, Street Soldier)



Black Mass (by Dick Lehr):

The biggest benefit Black Mass had on all of the books was it was the first one – by a mile. Most of the other books came out in later years. When I watched “The Departed”, it really reminded me of Black Mass. The book is told by two Boston Globe reporters who had investigated the story back when it all was unfolding in the 80’s and 90’s. It keys in on the relationship between Whitey Bulger and the FBI. Its main characters are Bulger, John Connolly and John Morris. It’s an easy read in terms of flow but I think the timing of it all was what gripped me the most. Nothing else was out there telling this kind of detail on the infamous Whitey Bulger. When I read it, there were some alarming details that were out of left field, that I don’t want to reveal. Stuff that seemed unrelated to the criminal aspects but were compelling nonetheless – jawdropping in fact – which were later corroborated in the other books.



While entertaining, I was somewhat disappointed as many of the aspects ended up being vague. What wasn’t vague was the Whitey and FBI relationship. That was brought out in thorough detail, the reason being that the reporters’ sources of information on the detail turned out to be from the FBI.



In all though, a solid book – it gives you the background, some details around some of the menacing ways of Bulger, and the reasons why he skated for as long as he did. These reporters don’t have an agenda. They are writing accounts of information they gathered. Perhaps the most unbiased look at the Whitey story of the 4 books I’ve read.



Grade – 7.9 out of 10



Street Soldier (by Eddie Mackenzie):

Not sure why I even bought this book when I did. Something to grab that might entertain me. Street Soldier is written by Eddie Mackenizie – who was, to put it simply, muscle for Whitey Bulger. This is a fairly short book and you can rip through it pretty quickly. It’s told through the eyes of Eddie “Mac” Mackenzie – his upbringing, his wayward behavior and his eventual connection to Whitey Bulger.



Mackenzie talks about his rough childhood, and how the military saved him. How martial arts provided him an outlet and an asset in the crime world. How he climbed into the underbelly of South Boston and eventually escaped – earning his college degree.



I don’t want to reveal too much, but the major undertone of the story relates to sexual crimes to minors – and it will pull you in. It’s laid out in unfortunate detail but it’s done for a reason. And later in the book, it blows you away. This aspect of the book saves it and makes it worth reading.



Like most authors who are the main characters, Mackenzie draws on your sentimental side to empathize with his plight. And you will to some degree. It was an ok book. The fact that it was short is a good thing really. It doesn’t bore you with page-filling details about himself or everyone else.



Grade – 6 out of 10



Rat Bastards (by John “Red” Shea ):

The only reason I bought this book was because my uncle was in it. Tom Cahill is my step-father’s brother. I’ve known “Uncle Tommy” since I was 7. And while my step-father, Dennis, told stories of all his brothers and sisters, the Uncle Tommy stories were the best. As an 8, 9, 10 year old boy, they were great stories. They were stories of bar room fights, and crazy behavior – they weren’t the stories that got him in real trouble – for Dennis, quite frankly, didn’t learn about them until later on, nor would he have ever told us those anyways.



In 1990, Uncle Tom was arrested as part of the Whitey Bulger sweep. When 50 or so guys went down for various criminal activities, most of which centered on selling cocaine in South Boston , he was one of them. As the story goes -- he was selling to an undercover DEA agent, and he once made the claim "You don't sell drugs in South Boston , unless Whitey Bulger gets a piece." That led them to think he knew more about the circumstances. Whether he did or not, I don't know - I only know that he served about 4-5 years in federal prison for the drug trafficking.



We didn’t visit Uncle Tommy in South Boston much. He mostly came to Lawrence to visit us. But one time we did go there, I was probably 14 or 15 years old at the time. So it was probably 1986 or so. While we were there a young guy stopped by. It was a bizarre kind of moment. Here we are, on a Sunday afternoon, just the family, and this young guy, probably in his early 20’s, pops in unnannounced. He visits for a little while and then leaves. And Uncle Tommy is telling my stepfather how he’s a good kid, tough kid, great boxer, a friend of his, blah, blah, blah… Dennis loved boxing. Especially young Irish boxers from Boston . What made it odd was this kid was young enough to be Uncle Tommy’s son. So it wasn’t as though they were close in age or anything. Anyways – kind of a random moment.



When everything unraveled, and Uncle Tom was going away, Dennis tells us that the kid who stopped by was part of the situation as well. That kid’s name was John “Red” Shea.



Rat Bastard is, like Street Soldier, told through the eyes of Red Shea. His upbringing, his rough childhood, and his experience as a boxer. If someone hadn’t told me that my Uncle Tom was in the book, I would have never read the book. But for personal reasons, that was interesting. Unlike Street Soldier, Rat Bastard is more detailed – and a longer read – somewhat self-indulgent but it weaves and interesting tale of how Shea didn’t work for Whitey in the beginning. Whitey got wind of his work and essentially acquired the business – which he did on many occassions in many different ways.



Shea’s book is a closer look at how Whitey used the people beneath him like pawns all in order to save himself. Shea portrays himself as a stand-up guy who never turned on anyone – and in his eyes, that should be all that mattered. In fairness to him, he doesn’t sugar coat his own life. He tells you on page 1 or 2 that he was a bad dude, and he follows through on the how’s and why’s, etc. Someone you really didn’t want to mess with.



This book is a grittier book than Street Soldier. It’s more violent, the language is like he’s telling the story right from his own mouth – more F-bombs than I can count. But there are no stunning moments like Street Soldier.



One interesting note on this – Mark Wahlberg has purchased the rights to the book and it wouldn’t surprise me if a movie is eventually made.



Grade – 6 out of 10





The Brothers Bulger (by Howie Carr):

Let me first say, prior to reading this book, I didn’t follow Howie Carr’s articles or ever listen to him on the radio. So I really had no opinion of the guy. Having read the book, I will now pay closer attention to him as I found this book to be a real treat.



While Black Mass came first and benefited from doing so, the Brothers Bulger came later and also benefited in its own way. Because this book came out after Stephen Flemmi had confessed to so much, it has a ton more detail than Black Mass. Details around the murders, the crimes, the FBI dealings, etc. But in order to paint a different picture than just having more details than Black Mass, the Brothers Bulger tells the story of how both Whitey and Billy combined corrupted Boston for 25-30 years. Whitey was a blatant criminal, while Billy Bulger was the Senate President and at different points in time, the most powerful politician in Massachusetts .



Carr pulls no punches – he doesn’t insinuate. He doesn’t lead you to believe X, Y or Z – he just tells you straight – Whitey Bulger killed this guy, that guy, etc.



It’s a chronological tale about the Bulgers, their roads, how they intertwine, etc. Unlike Street Soldier, or Rat Bastard, there is no empathizing with any characters, except for maybe some of the innocent victims. In the process, Carr rips Billy Bulger, Whitey Bulger, Flemmi, Kevin Weeks, Dukakis, William Weld, John Connolly and a host of other notable Massachusetts names.



Simply put, I thought this was the best book by far. It shows you just how powerful Whitey Bulger was and why. Not only did he have his FBI contacts, but his brother the politician. Carr talks about how Bulger and Flemmi offered “protection” and between the FBI and his brother – it seems as though Whitey had plenty of protection.



The first part of the book, Carr lays into Billy Bulger for what appears to be standard politician stuff – so it seemed a little overboard. Until you get into the later stages of the book and it details the political corruption. The kick-backs, the laundering, the cold hard cash finding his pockets. Meanwhile, the Whitey Bulger stuff is simply better than what Black Mass brings – it’s direct, to the point and as plain as day.



It seems like Howie Carr has an axe to grind throughout the book, but without knowing him, and if I take the book on its presentation, I thought it was very good.



Grade – 9 out of 10