Whitey’s Handler John Connolly — Blind Man or Con Man?

Edward MacKenzie in his book Street Soldier tells about US Attorney Mike Sullivan stating after Connolly was convicted that he was “a Winter Hill Gang operative masquerading as a law enforcement agent.”  MacKenzie then wrote, “Welcome to the club, Johnny.  You’ve officially been outed” expressing his satisfaction with Connolly’s conviction.

He goes on to write:  “I actually have mixed feelings about the former FBI agent.  He was always respectful to me, though I understood he would sacrifice me at any time to get a star on his forehead.  But I believe the FBI was as much to blame as he was.  After all, where did they stick him?  His old neighborhood! That’s entrapment as far as I am concerned.  How could he betray his childhood buddies?”  

MacKenzie believes a cop who thwarts the criminal activity of a gangster he was friendly with as a youngster amounts to a betrayal.  It’s a skewed notion of a criminal mind but a good insight into how even a self labeled reformed criminal thinks.

MacKenzie tells about meeting Connolly in January of 1999 at a Bruins game (Connolly will be indicted in December, 1999) .   A former coach of the Bruins who led the team to the Stanley Cup Championship told me that Connolly used to be a big Bruins fan.  He accompanied the team on some of its trips and liked to go to a North End restaurant with some of the players.   Hearing MacKenzie tell me he met him at the game did not surprise me.

At the end of the first period he met Connolly at the landing above their seats.  Connolly complained to him about the US Attormey’s Office and former AUSA Jeremiah O’Sullivan.   He said O’Sullivan knew everything he was doing and avoided testifying by faking a hear attack.  (You can read about O’Sullivan in my book.)

Connolly went on to say, “But, hey, Eddie, you know that Whitey was very appreciative about what you did with the FBI.  He called it a  masterful move.”

Eddie replied:  “I wasn’t rolling on any of my boys.  No fucking way.”

Connolly responded:  “Yeah, you played it like Whitey.  Work it  but don’t sell out Southie.”

MacKenzie came back saying Junior Patriarca told him Whitey sold out his guys in Southie.  Connolly replied it was a lie.  “Whitey never, ever, ratted on any of you guys!  He was stand-up. He was a killing machine, but stand-up.  You know that, Eddie.

MacKenzie came back at him, “And he didn’t peddle drugs, Johnny?

Connolly replied, “Eddie, Whitey was a lot of things, but he wasn’t a drug dealer.

Connolly’s answer is baffling.

Here’s Connolly who was using Whitey as a top echelon informant (the polite word for big rat) spinning out a story that Whitey never ratted on Southie guys.  MacKenzie, John ‘Red’ Shea and others of the 51 muffs in Southie arrested in August 1990 felt Whitey betrayed them.  (In my mind the jury is still out on that.)

There’s little doubt that Whitey never considered himself a rat.  Connolly obviously didn’t.  But then again MacKenzie didn’t consider himself a rat because he wasn’t giving information against his friends from Southie but against others.  The more we see of the gangster mind we see everything can be justified.

It gets worse.  Connolly is telling one of Whitey’s drug dealers who paid Whitey $20,000 a week that Whitey wasn’t a drug dealer.

Is it possible that Connolly believed these things?   I suppose it could be argued that with respect to the drugs since he did not handle any of the product himself he was not a dealer.  Using the same thought process you could say Charles Manson never killed anyone because he didn’t plunge the knives into the victims.  Or Osama bin Laden didn’t attack the Twin Towers on 9/11 because he wasn’t in one of the planes.

Pushing it further, you could say Whitey tried to keep drugs out of Southie because he charged drug dealers a fee to operate there and he was trying to make it too expensive for them.   It pretty much shows you can make of things what you want.

MacKenzie has Connolly professing Whitey wasn’t a rat and that he had nothing to do with the drugs in Southie.   Connolly will also say he had no idea Whitey had killed anyone (which seems to undermine his statement he was a killing machine) or that he and Stevie Flemmi were running a criminal empire.

Connolly was an FBI agent in the organize crime section.  He was surrounded by supposedly top notch agents assigned to that section.  They were under the command of the best organized crime fighters in America.

How do you explain Connolly — willful blindness or a little bit of the con?

A good site with pictures of Whitey,

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