Here’s a good piece in Salon on how recently captured Boston mobster James “Whitey” Bulger always had a friend in columnist Mike Barnicle:

In the summer of 1991, James J. “Whitey” Bulger won the Massachusetts lottery. Well, at least he claimed he did. The $14 million winning ticket was actually held by a South Boston man named Michael Linskey, who had purchased it at the Bulger-owned South Boston Liquor Mart. Linskey then told state lottery officials that he’d actually been partners with Bulger and two others and that they were entitled to half of the jackpot.
This was all enormously suspicious. It had long been known that Whitey Bulger, whose brother Billy was then the most powerful politician in Massachusetts, lived on the other side of the law, and by ‘91 it was becoming clear — and, the closer you looked, glaringly obvious — that his crimes included racketeering, drug-running and murder. He wasn’t just the neighborhood bookie in South Boston. In fact, the only reason he owned the South Boston Liquor Mart was because he’d paid a visit a few years earlier to its previous owner, Stephen “Stippo” Rakes, intimating that Rakes’ child might be harmed if he didn’t agree to sell the store to Whitey. Similar coercion, just about everyone figured, accounted for Whitey’s lottery score.
But not the most influential columnist at the biggest and most influential newspaper in New England. Mike Barnicle took to his Boston Globe column to issue a ringing defense of Whitey — a man he always called “Jimmy,” the name that only the Bulger family used — and to lash out at anyone who would suggest malfeasance. “Give Whitey a Break” began with this:
In a blatant display of prejudice against local Irish gangsters, some narrow-minded bigots are hinting the Lottery was rigged simply because a friend of Jimmy Bulger’s won $ 14 million and split the lucky ticket four ways. Next, in a gross display of piling on, the state treasurer, Joe Malone, said he was disturbed that the guy who sold the winning numbers, my pal, Kevin Weeks, showed up at Lottery headquarters “with a reputed mobster,” and I think he meant Bulger.
Barnicle continued:
Hey, good things happen to good people, right? Of course, there is an army of malcontents who refuse to believe that the result of a mere game of chance is on the level when the cash cow moos at the doorstep of a man – Bulger – who, according to illegal eavesdropping by FBI agents and their cheap equipment (And I will show you how lousy their stuff is), runs a vastly overrated criminal enterprise in the area.
And finished with this:
So, lay off Jimmy Bulger. For the first time in his life, he got lucky, legitimately, and won the lottery. Knowing him, he probably already has handed out money to St. Augustine’s, figuring that when he goes – and the odds on that are better than winning Mass Millions – there will be some people left behind who will say, “Not a bad guy.”
This was the same Jimmy Bulger, of course, who was overseeing a massive criminal operation, one that poisoned the streets with cocaine and other illegal drugs and claimed dozens of lives. Whitey himself had taken part in numerous killings, and his victims weren’t all fellow mobsters.

The rest here.