Whitey and Me: My Black Mass Moment

6 minute read

So the phone rang, finally, late that Monday and it was Callahan. I had been chasing him, in a way, and he had been unresponsive. Not peculiarly unresponsive, considering the circumstances, but unresponsive.

He said essentially, on that Monday evening, “you’ve been calling,” and I said essentially that I had. He said he had no comment, which was fine as it was expected, and insisted that I take his name out of the piece, which was impossible. He said something along the lines of “You know what can happen.” I got the gist; our conversation closed. I was scared witless, of course. We printed anyway.

All of this comes to mind because of a movie that’s opening Friday, Black Mass, in which Johnny Depp plays Boston gangster Whitey Bulger. It’s weird the way things sometimes turn, or turn up later, and you come into play with folks—like folks from the Winter Hill Gang. I am writing this, age 61, strictly from memory. My notes were long ago filed at Time Inc., where most of this reporting was done for Sports Illustrated, and I presume those notes are dust. Once, they were required, even by—especially by—“Legal.” Today, especially with Whitey having gone away and almost everyone else having been offed, as they used to say in the colorful parlance, I think they are not legally essential.

What in the world am I talking about?

I was in the office, in the spring of 1981, a kid reporter on the Scorecard section of Sports Illustrated, and I’m reading the morning paper, which used to come for free, back when we had expense accounts, too. This fellow named Roger Wheeler had been shot and killed on a golf course in Tulsa, Okla. That seemed strange, so I read a little more.

Anyway: golf. Might be for us? Golf’s a sort of sport, right?

As the morning evolved, I talked to my brilliant editor on Scorecard, Jerry Kirshenbaum, who encouraged me to look into it a bit more. Turned out it wasn’t about golf, but jai alai. Well, heck, that’s a sport too, sort of. Wheeler had owned a jai alai fronton in Florida, and Callahan, a mobster wannabe from Beantown, had been installed by Whitey as boss, because Whitey knew how crooked and profitable jai alai could be. But Wheeler was an innocent, and Wheeler didn’t like all the crookedness that he found out about, he wanted to sell his fronton that Whitey was basically running and Whitey sure didn’t want him to, and well, you know. Wheeler winds up dead, and eventually Callahan, too. Not sure if all that is in the movie, but I’d bet some of it is.

So I say to Jerry Kirshenbaum, “The story’s not in Tulsa. Not even in Florida. It’s actually in Boston.” I didn’t say Beantown, because Jerry’s not from there. Jerry says, “Head on up.”

I booked an off-the-record interview with an FBI agent. I swear to high heavens that I don’t know if it was Connolly. Again, my notes are long gone. What I do recall: The fellow was very, surprisingly, forthcoming.

In about three days, racing against the Wall Street Journal, Jerry and I figured out that the Winter Hill Gang had killed Wheeler. We nailed our story down with Legal at Time Inc., and we closed our piece—as SI always did, on Monday. Sandy Padwe, our investigations editor and a very dedicated (and let me say it: very sweet) man who would later go on to run the journalism school at Columbia, had become involved. So he comes into my cubicle to give me a pat on the back and says nicely done. He leaves, and I continue to pack up my notes, hoping to join my colleagues at Runyon’s or wherever we’re meeting that Monday. We would always convene on Mondays, back when we were young enough.

Then Callahan calls, finally, after I’ve been chasing him, and threatens my life.

I was so young, scared and conditioned, my response was basically, “So you don’t want to respond on the record? Or do you? Or ‘No comment’?”

He said in flagrant terms that he chose not to respond, and that I might wind up dead, and then we closed our conversation, and I reported what had happened to Sandy, and that was that. So I hastened to Runyon’s and an ale.

Within not too long a time (about a year, as I remember), Callahan was dead in a car at Miami International. I had never before and have never since been glad to hear that a man or woman was dead.

The movie brings this all back.

Weirdly, that wasn’t the only time I found myself between sports and the mob. Remember the Boston College Point Shaving Scandal? Basketball? I was on that, too. I traveled up to Boston, and even stayed at this pretty crappy Logan Airport hotel, in the exact room where part of the deal had gone down, in order to write “atmospherically” about the . . . let’s call them, “shenanigans.” Next day, I enjoyed a fascinating session with Harvard’s basketball coach, who ran footage of film back and forth for me to show how B.C. had cheated—dumped—in the game against Harvard. I was dragged in by Time Inc.’s “outside counsel” at one point to say what I might say if I was deposed at the trial in Brooklyn. I never had to testify. The verdict for Burke (the guy De Niro played in Goodfellas) was guilty.

Goodfellas, 25 years ago just now, and of course the new movie… I could have a film fest for the kids this weekend.

But I think I’d rather not. Not my kinda guy, Whitey, though I hear Depp’s pretty good.

Robert Sullivan wrote and edited for Sports Illustrated, TIME and LIFE from 1980 to 2015.

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