My Cousin Joe Was a Hitman for the Boston Mob
Above: Members of the Winter Hill Gang, including the notorious James “Whitey” Bulger (bottom right) and the author’s cousin, Joe McDonald (top left).
My cousin killed people.
At least, that’s what I’m told. I never met Joseph McDonald, but word is he preferred using a handgun. He liked to get in real close so that the soon-to-be deceased could figure out what was coming. His intense, bald visage would be the last face they would see on this earth.
He was my grandfather’s first cousin, my first cousin twice removed: a bookmaker, loan shark, thief, World War II vet, drunk, killer. He was a member of the Winter Hill Gang, the most notorious Boston-area outfit of the last half-century. There are Winter Hill guys who have admitted to murdering 20 people, guys who tried to run guns for the IRA, and guys who fixed horse races up and down the East Coast.
Some of the Hill’s associates started grabbing headlines in the early 1960s. Some of them, like James “Whitey” Bulger, continue to do so to this day. Lots of people died. Lots of people were sent to prison. So being related, even distantly, to one of the main players in that gang is, well, strange.
My father’s family—a clan of nurses and engineers—know next to nothing about Joe, who died in 1997. They are not the sort of people who rob warehouses or break out of prison.
The author’s cousin and Winter Hill Gang member, Joe McDonald.
One of my aunts says there was shame, that my grandfather and his siblings were law-abiding folks who couldn’t relate to Joe’s life. Joe’s name was never mentioned. The relatives who did meet Joe only did so once or twice, and memories are slippery things.
Did he get pinched in a New York City train station while dressed as a nun with a machine gun under his habit? No, says another one of my aunts, the machine gun was in a hockey bag. There was no habit. It was all over the news, she says.
A Day in the Life of an Alzheimer’s Caregiver
My dad was diagnosed with Alzheimer’s about three years ago. After an extended stay at the hospital and stints in two different rest homes, my mom brought him home to care for him herself. She did this despite warnings that it would be too much for her to handle—even with regular assistance—because the conditions in the homes were too depressing to bear. There is an unseen routine in the lives of most home caregivers that makes Michael Haneke’s Amour look like Sesame Street. I wanted to find out what the day-to-day life of someone tasked with keeping another adult alive is like, so I talked to my mom about it.
VICE: How does your average day begin?
BB: Usually I wake up before LD and get dressed, and I try to get the coffee made and the cereal stuff out. But if he wakes up first, I just get him cleaned and dressed and then do the other stuff.
What time does he get up?
He’s gotten so he goes to bed between 8 and 9 PM and sometimes sleeps until noon. One day I was so tired and exhausted that I didn’t hear him and he got up and went into the den at seven in the morning. He ended up somehow falling, and I found him on the floor tangled up in the chair. But usually I wake up before him and get dressed real quick, because if I don’t he watches me do every single thing, and it drives me crazy.
Why does he watch you?
Because he doesn’t have anything else to do. He just stares. And he wants to see what food I’m making.
I know he usually wets the bed at night, even through the disposable underwear. Do you change the sheets after you wake him up?
I take the sheets and the pajamas and the shirt and socks and just wrap them up in that plastic liner that keeps the mattress pad dry. Sometimes if he wakes up before I do he’ll have already taken his underpants off. I get him to the bathroom and have him sit on the toilet so I can get his wet clothes off and wipe him off with Handi Wipes.
Prisons Punish Families Too
When I read articles like this one in the New York Times about how prison makes people poor and destroys families, I have mixed emotions. I think it’s admirable that this high-and-mighty mainstream paper is examining the effects of the nation’s prison population explosion over the past 40 years. The author, John Tierney, tells the story of Carl Harris, a guy from DC who used to sell crack until he beat up some of his customers who robbed him and got 20 years on a trumped-up charge because the cops thought he was some big-time drug dealer. Sounds like Carl is doing better now, and I’m real happy he’s gotten to the point where he can enjoy life. Sadly, I ain’t exactly there yet—the drug statutes of New York State are continuing to butt pump my unlucky rump, even though I’m out of prison.
I could repeatedly point out injustices I believe I’ve incurred over the past eight years, however, I’m trying to stop that train of thought and get back to basics. I’ve been beating off to my old Susan Powter videos like it’s ’94 again and thanking whatever there is to thank up there that I didn’t get 20 years for beating up crackheads. As that Times article demonstrates through Carl and his family’s story, some prison terms are WAY too long, and excessive sentences unnecessarily handicap communities already in dire straits. Basically, prison is responsible for more chaos than anything else. But if it took the Times writing about it for you to get that, you’re probably a simpleton who needs some help eating solid food.
I didn’t go to Harvard or Yale and by many peoples’ accounts I’m dumber than dookie-dipped dewdrops drying on a dildo, yet I know prisons better than the front of my dick. While the clink-clink blows balls on a number of levels, the one aspect of doing time that, at least in my experience, isn’t that bad is the one the media plays up the most, and that’s the actual physical doing-time part. Movies and shows depict prisons as full of bloody dicks and shivs, and no doubt, dirt gets done in prison. But actually, most motherfuzzies in jail deal with a lot iller shit in the streets. The prisons I’ve been to were all pretty much chillin’. It’s basically summer camp minus the baby beavers. Lots of us bitch and moan, but we play cards and sports, watch TV, eat free food, have people clean up after us, lift weights, listen to music all day, take profucive naps, read and write a lot, and get money (masturbate) till the cows come home. The best part is you taxpayers pay for it all!
GUN-CRAZED AND DANGEROUS, MY AUNT DEBRA HAUNTED MY FAMILY FOR 20 YEARS
Foreground: Debra enlisted in the US Army in 1969 as a second lieutenant. In late 1971, after she had been promoted to captain, she received a letter stating she would not be retained for active duty. Photo courtesy of the National Personnel Records Center. Background: This suicide note was found near Debra’s body, along with a Bible opened to Psalm 23. Note courtesy of Janna Sorg.
It was Christmas of 1990 in my grandmother’s house. The thick, heavy curtains in the living room were drawn. My mother and I sat on the edge of a bed. In an armchair across from us sat Aunt Debra, my mother’s sister, who also lived there. In another sat my grandmother, who was in the middle stages of dementia. Around the room were several end tables and chairs. Sitting on each was a gun.
We had not planned to exchange Christmas gifts, yet Debra was handing me a .38-caliber handgun with a box of bullets, a holster, $100, and a note.
“Read it later,” she said.
At some point in the afternoon, the conversation deteriorated. Debra reached behind her and pulled a bullet from a box on a nearby bookshelf. She held it between her thumb and forefinger, looked at my mother, and said, “Janna, this has your name on it.”
My mother and I hurried down the driveway to our car, parked outside the ten-foot fence strung with razor wire that surrounded the property. As my mother turned the ignition, I glanced back and watched Debra run down the hill toward us. She was wearing a black ski mask, a camo jacket, blue jeans, and black boots. Her dark figure contrasted with the white snow, except for moments when she disappeared behind the pine trees. I stood with one foot in the car and the other in the snow. As Debra approached, I could see the vapor exhale from the mouth hole of her ski mask.
“I’ll give you this one, too,” she said, handing me a semiautomatic 9-mm with a box of bullets. She showed me how to load and unload the clip.
“Don’t blow us all to hell, Debra,” my mother yelled from the car.
“Merry Christmas,” Debra told me.
“Merry Christmas,” I replied. “Thanks for everything.”
unt Debra was notorious in the rural hamlet of Indiana where I grew up. For most of her adult life, she had threatened and attempted to kill people. My grandmother, by throwing a pan of hot grease at her head, and later by drugging her with medicine stolen from the psych wards and nursing homes where Debra worked. My mother, who Debra saw as competition for affection. My father, who, she claimed, would be felled by a hail of bullets unloaded into the side of his car. Her supervisors, who were reluctant to fire her for fear she would return to the workplace and shoot them. Her coworkers, who she had accused of “working at cross purposes” and plotting against her. The stranger on the street who looked at her the “wrong way.” The kids playing across the road she fired two shots at one day because they annoyed her. “She unnerved and frightened me, and I feared for the patients,” one of her bosses told my mother. “Her stare was pure evil.”
Yet for most of her adult life, Debra never killed anyone.
My grandmother was 40 years old when she had Debra—her first child after trying to get pregnant for 22 years. My mother was born just over a year later. She had always felt that her older sister wasn’t quite right. “When I said my prayers at night, I asked God to take some of my happiness and give it to her,” she told me. As a child, Debra hallucinated. She would sit in a chair and enter a trance. “You could get in her face and scream,” said my mother. “She’d never come out of it.”
In 1969, Debra enlisted in the US Army at the height of the Vietnam War. There she won marksmanship awards and was trained in the fundamentals of counterinsurgency, psychological operations, unconventional warfare, survival, escape, and evasion.
Four years later, having risen to the rank of captain, Debra received a letter from the Army saying she would no longer be retained on active duty. She was tossed out along with a friend—another woman. She moved back home.
About four years ago, photographer Johanna Heldebro’s father abruptly left his family in Montreal and relocated to his native Sweden. Johanna’s parents had just finalized a sudden divorce after Mr. Heldebro disclosed that he was having an affair with a mother of two who lived in Stockholm. Of course, everyone was angry and confused. But instead of writing her dad’s name 30 times on a piece of paper in black ink and burning it over a black candle, Johanna decided to use the unfortunate situation as inspiration for her artwork. She traveled to Sweden to stalk her dad and find out about his new life firsthand.