Comedian, Playwright, George MacDonald takes a ride with Whitey Bulger

George MacDonald

 **** Well, when you work three jobs like I do, you meet a lot of interesting people. And because I am a local journalist, I get to interview a fair number of interesting people. Have if you will... one Mr. George MacDonald, a comedian, playwright, and for now--a night counselor at McLean Hospital, where I work. George and I were like two ships passing in the night. I was leaving the 3 to 11 shift and George was starting his usual graveyard. George looked like an interesting dude, and so we eventually got talking. George is originally from Southie, and was part of the comedy explosion here in Boston in the 80s and 90s. Since we are both a year or so on either side of 60-- we knew a lot of the people, places, and folks on the scene for the past decades. George is good friends with the comedian Jimmy Tingle, who I worked with when I ran The Somerville News Writers Festival. He had great anecdotes about many of the other great comedians, poseurs, players, what have you... in Boston and L.A.--his stomping grounds during his career.   Here is a brief bio for George:

Actor, comedian and writer, George J. MacDonald is pleased to be artistically involved with Somerville once again. Stage plays that Mr. MacDonald has written include, Waiting For Whitey,  At The Funny Factory,  In A Better Place and Whistling Past The Graveyard.  Screenplays include, Both Guns Blazing,  Still In The Picture and The Spider Sequence. Some of Mr. MacDonald’s film credits are,  Monument Ave. , Celtic Pride, Bluff and When Stand-up Stood Out.  His television credits include,  MAD-TV, The Michael Richards Show and A&E’s Comedy On The Road.  In 2005, George made his directorial debut with Why Work? , a sketch comedy show that appeared in The Edinburgh Fringe Festival.  Mr. MacDonald is a member of SAF-AFTRA, Actors Equity Association and The Dramatists Guild of America. 

George, a former Somerville resident, was kind enough to share an essay about his experience with the notorious Whitey Bulger. George wrote a play Waiting for Whitey that was staged in Boston, and got a great review in The Boston Herald and elsewhere.

Hitching a Ride with the FBI’s Most Wanted 


by George J. MacDonald



As soon as I got in the car, I knew I’d made a mistake. From the curb and through the windshield, the driver resembled a guy who attended U. Mass Boston’s Harbor Campus, same as I did. But now, sitting next to him in the front seat, looking into those laser beams he had for eyes, I knew exactly who this individual was. James ‘Whitey’ Bulger. The Irish mob boss of my South Boston neighborhood, a man reputed to be a ruthless killer.

It was early March, 1977. Sunny. About three o’clock. The air was crisp. I had cut my last class of the day and felt very tired as I thumbed a ride along the boulevard on Carson Beach. My fatigue, combined with the joint I had just smoked, severely impaired my powers of observation. When the car pulled over to the curb, I was filled with a surge of gratitude. I jumped inside, delighted to have escaped the late winter chill. I was lit up like a Christmas tree and feeling more friendly than a golden retriever.

“Hey, big guy! How ya doing?”

Not a word. Just his icy stare boring holes into me.

“Sorry. Didn’t mean to be rude. You looked familiar. Thought you were a friend from school.”

His eyes softened a bit at the apology. Thank God my parents had raised me right.

“You probably do recognize me. But not from school.”

As the reefer haze in my brain cleared, the situation began to come into focus. Sitting beside a sociopathic murderer tends to have a sobering effect on most people. I finally recognized him and knew that this was not good.

“My name is Jimmy. Jimmy Bulger.”

“Oh yes, of course. I’ve seen you around the neighborhood.”

I introduced myself and we shook hands. He asked me where I was going so I told him. He pulled away from the curb and an awful lot of questions raced through my mind. Why does this hardcore gangster want me to know who he is? Is he looking for an alibi? Where’d he hide his gun? Is there a body in the trunk? This is a wiseguy of the heaviest caliber. Why is he picking up a hitchhiker, even if it is another person from Southie?

He talked a lot and I listened. Whenever you find yourself in the company of a stone cold killer, it’s always a good idea to yield the floor. He wagged on and drove the most circuitous route imaginable to my destination. He dropped me off exactly where I was going and I thanked him for the ride. He told me he’d see me around. I said sounds good to me, all the while hoping that such would not be the case. Only ten minutes had passed. I’ve never been so happy to get out of a car in my life.

Things have changed a lot for me since 1977. I haven’t smoked marijuana or hitchhiked for almost thirty years. I’m much too long in the tooth and those are a young man’s games. Things have changed a lot for Whitey, too. He‘s gone from being a local crime boss, to an FBI informer turned fugitive, to a lifetime guest of the federal government inside The Crowbar Motel.

I’ve often wondered about my ride with the FBI’s Most Wanted. What compelled him to pick me up? What motive could he have had for doing this? A notorious desperado and shooter like him, going out of his way to give a free ride to a total stranger and civilian like me? He had nothing to gain by giving me a lift. So then why did he do it? What was that all about? Guess I’ll never know.

I’m glad they did finally bring him to justice. He caused too much pain and suffering for a clean getaway. Whitey Bulger is now behind bars and in his eighties. He’s another old killer in an orange jumpsuit who must answer for his sins. Had he died while a fugitive, living under an alias, he might never have been found. His tainted legend could have drifted into the realm of the unexplained, right beside D.B. Cooper and Jimmy Hoffa, Area 51 and the Roswell crash. That place beyond the pale where things go bump in the night. Then my tale of the road might become merely one more ghost story ‘round the campfire, like an Elvis sighting, a Bigfoot encounter or a boat ride through the Bermuda Triangle.

Some people may find my story hard to believe. But it is true. And after sitting in his car and looking into those maniacal eyes, I can honestly tell you that Whitey Bulger was no Flying Dutchman.




*****George J. MacDonald is an actor, playwright and former resident of both South Boston and Somerville. He has also lived in New York and Los Angeles, but will always be a Bostonian at heart. He plans on maintaining his East Coast sensibility by never developing a taste for sushi or ‘taking’ meetings.