Advertising in the Boston Herald WORKS!
Always has, always will. Just consider this classified ad from February 1992, in which one of the bosses of the Winter Hill Gang sought out an old pal, who had gone on the lam after losing big money he didn’t have on a Super Bowl XXVI bet.
Joe McDonald was seeking “Jimmy S. of Winter Hill” to pass on some “Important news for him.”
The important news was, you’re a dead man. But Jimmy Sims apparently couldn’t read between the lines. He responded and was soon buried in a shallow unmarked grave in Quincy.
Joe McDonald – another satisfied advertiser of the Boston Herald.
The disappearance of Jimmy Sims has been a mystery for more than 30 years. And now it seems to have been solved, in a fascinating new book about Boston organized crime by Springs Toledo.
It’s entitled “Don’t Talk About Joe Mac: The Life, Wars and Secret History of the Man Behind the Winter Hill Gang.”
Toledo spent years researching the book, and it’s probably the last of the great Boston Mob books. Even if you think you’ve read everything there is to know about the Somerville crew, there is a lot of new stuff in here, and not just the apparent solution to the Jimmy Sims hit.
Joe McDonald, the subject of the book, was the oldest guy in what became the Winter Hill Gang. He was a World War II vet, had been on the USS Quincy when it was torpedoed by the Japanese in shark-infested waters in 1942.
Joe Mac survived, but his younger brother didn’t. He was never the same afterwards.
Even in the Hill’s crew of world-class cut throats, McDonald stood out. Toledo has him for 41 murders, behind only maybe Stevie Flemmi, if the Rifleman is telling the truth about his “50-60 murders.”
McDonald also made the FBI’s Ten Most Wanted list, much earlier than Whitey Bulger.
Joe Mac may have been the only member of the gang who had a murder in the Pacific Time Zone. In 1976, at the age of 59, he shot a rare-stamps dealer four times in his garage in Sierra Madre, California as his horrified wife looked on.
Joe Mac’s only disguise was a handkerchief over his mouth. Subtlety was not one of his trademarks. During the Irish gang wars of the 1960s, he took an acetylene torch to the private parts of one of the McLaughlin hoodlums.
Joe Mac was a shrewd judge of character, at least about Whitey Bulger. After Bulger was welcomed into the gang by Howie Winter, McDonald never again set foot in Howie’s garage on Marshall Street.
Whitey of course was a world-class conniver. He was always scheming, looking for new ways to rid himself of dangerous rivals.
In the early 80s, the feds passed a new law. It imposed a sentence of 30 years on and after the conviction of any felony that involved the use of an unregistered machine gun.
Whitey immediately laid in a store of machine guns and began handing them out like candy to anybody he was afraid of. Then he’d call the cops on his payroll – the FBI.
He gave one to Pat Nee before an armored car heist, even removing the firing pin to render it inoperable, except to keep Pat in prison forever.
In 1982, Joe Mac was on the lam, heading back to Boston from Florida on the train. Whitey asked him to take something north in his suitcase – a submachinegun. The cops nabbed him at Penn Station in New York City.
McDonald knew very well who’d set him up. Looking at those extra 30 years on and after, he filed a motion, which Toledo reprints in his book.
“The defendant seeks the names and addresses of informers whose information will be relied upon at trial. The defendant does not claim that such disclosure will aid his defense.”
No, but it would have confirmed Whitey’s rat-hood, as informant BS 1544-TE. It would have meant Whitey’s elimination, and more importantly for at least a half-dozen FBI agents, the end of the hundreds of thousands of dollars in bribes they were pocketing from Bulger.
And so the machine-gun count vanished from Joe Mac’s indictment. He was back out on the street in four years.
There’s so much great material in “Don’t Talk About Joe Mac.” But to me Toledo’s biggest scoop is solving the disappearance of Jimmy Sims in 1992. Eighteen years younger than Joe Mac, Sims was basically his partner in crime. They went on the lam together, were a two-man hit team.
Sims was the fastest car thief in the gang. Martorano says he could steal a car in under 60 seconds. Sims preferred Fords, don’t ask me why. For all their hits, the Hill needed a lot of hot cars. They called them “boilers.” Sims was their go-to guy.
But he was also a degenerate gambler. He’d been cut off by everybody in Boston, so he took to betting with the Mafia in New York. His final wagers were on the 1992 Super Bowl. He took the Bills, so you know what happened. All Buffalo bettors die broke.
Joe Mac was told he had to handle his partner, or New York would. According to Toledo, Sims was lured out of hiding by Joe Mac’s classified ad in this newspaper. Joe Mac got him into a car in Quincy, shot him and then buried him in a swampy area off Fenno Street.
Maybe Sims’ body could still be found, but probably not until Norfolk County gets a new DA next January. Even if Meatball Morrissey’s State Police did unearth Sims’ remains (doubtful) the troopers would probably declare that he killed himself, like they did with Sandra Birchmore.
Joe Mac had been on the wagon, but after Sims’ murder, he went back to drinking again. He died in 1997, at the age of 80. There was no paid notice in the Herald that time. I had to call a source at Somerville City Hall to confirm his passing.
Don’t Talk About Joe Mac – it’s a great book, buy it. And if you have to find somebody who needs a rocket in his pocket, buy yourself an ad in the Herald.