by Greg Allard

In anticipation of  the upcoming release of his first auto biopic due out later this year called Confessions of a Bronx Bookie, Tunegroover is republishing the story I did of him in Insite Magazine after having just sat down outside Gainesville’s downtown Starbucks with former 911 New York Fire Lt., Bronx bookie, attic, bartender, restauranteur, and now stand-up comic and writer Billy O’Connor in late 2010. In our talk you’ll find a determined but philosophical man with a mouth full of politically incorrect wit and tip-of-the-iceberg expletives on what appears to be a semi-late-life journey toward name, fame and glory.

Originally published in Insite Magazine 

Having just hit the gym, he looks worn but fit for a man nearing 63. He sits at a table outside Gainesville’s downtown Starbucks, smoke billowing up from his cigarette and wrapping around his face as he looks down at the latest addition of his column in the Independent Alligator “Confessions of a New York Bookie.”

He was born in Ireland in 1948 and arrived in New York at 2-years-old when his parents migrated there. That was a while ago and it takes him a moment to remember it’s 2011. Now he’s a college senior.

“Just looking at the local rag,” Bill O’Connor says, putting his cigarette out and grinning at the prospects of a writing career so late in life.

A New York City firefighter for nearly three decades, O’Connor became a Bronx bookie for five years from 1990-1995. Now he frankly and not-so frankly writes about it in a style that makes it hard to discern fiction from non-fiction.

He talks to you in his strong Bronx accent like you’re an old friend, even if you’ve only known him for a few weeks. There’s something endearing in his demeanor, like he’s giving you the right directions into Manhattan and there’ll be no need to ask anyone else.

His voice is sometimes loud and hoarse. He wheezes periodically as he catches his breath, and then continues, looking straight into your eyes. Sometimes he lowers his tone and touches your arm like he’s letting you in on some valuable information. Like George Carlin, he has a knack of complaining about all the other a**holes while assuring you that you’re okay by him.

“I was a bookie and a lot of the stories are true and a lot are embellished,” he says, leaning forward. “I’m not proud of it but I was going through a divorce and sometimes you do what you have to do to get by.”

Now he talks like a man who takes the craft of writing seriously.


“You want to make it readable; you want to make it fun. Fiction has to be believable, truth doesn’t. Where does it start and where does it stop? That’s your fucking problem. You figure it out.”

Some of his former, let’s call them “associates,” called and asked him nicely not to mention their names when they caught wind of what he was up to. O’Connor has obliged them.

O’Connor, also a stand-up comedian at local clubs in Gainesville, is currently in his last semester at UF. He recalls seeing his comic hero Rodney Dangerfield in Atlantic City from the first row.

“I laughed my balls off for two-and-a-half hours, but when I got out of there, I couldn’t remember a single joke.”

Bill makes no apologies that he doesn’t stay too abreast of popular culture.

“It’s always changing,” he says. “Ten or fifteen years ago, almost every white man in the country wanted to fcuk Whitney Houston- –now look at her, she’s a crack-head.”

“I can’t keep up with that stuff,” he says, “so I tell jokes about something that transcends all generational lines — sex.”

“He’s absolutely filthy,” says master lecturer and University of Florida journalism professor Mike Foley, who was a judge at a comedy contest that O’Connor won second prize in.

“The two other judges were young women in their 20s who were hiding their faces from the stuff that was coming out of his mouth.”

For Foley’s money, O’Connor was the funniest guy there.

Last fall, O’Connor was contacted by Adam Berry, sports editor of the Alligator, through a classmate in his editing class, to see if he might be interested in writing a column on gambling. Offered creative freedom, Bill jumped on the opportunity.

“I’ve never seen a winner,” he says. “I want to impress kids that you can’t win.”

“I can’t watch sports anymore since I quit gambling. I lived and died on every game, I used to wager $10,000 per game. Now, for me, watching sports is like watching grass grow.”

When O’Connor retired from the fire department, he and his girlfriend flew south to Gainesville, where Bill’s three kids, now 33, 30 and 27 lived, and where he figured he would do something he always wanted to do, go back to school.

To get into Santa Fe Community College in 2007, O’Connor had to write an English paper “to find out if I was literate,” as he puts it. A Vietnam veteran who leans way to the left politically and is very outspoken, he wrote a paper comparing the war in Iraq to the Vietnamese War, which not only displayed his writing prowess but was also good enough to be published at the muckraking leftist newsletter When the USA Today online picked it up, his inbox was soon jammed with more than 300 emails.

“I said, ‘Wow—fuck man! Maybe I can write,’ ” O’Connor says.

When he asked his girlfriend for advice on what to major in, she suggested journalism over English. O’Connor agreed, he wanted to learn how to write but didn’t want to have to labor over Chaucer or Dickens.

“I had my fill in high school,” he says.

O’Connor describes himself as manic and compulsive who has done a lot in his life—most of it to the extreme. Besides being a vet, firefighter and bookie, he tended bar, owned saloons and restaurants. He readily admits to have taken lots of drugs and alcohol.

“I don’t do that anymore, except for marijuana every once in a while,” he says with a hoarse laugh.

From the get-go, he wanted to write about his experiences in a straight no-nonsense style of subject-verb-object and then move on to the next one. When he took advanced composition, he approached his professor, William Bowers, with a concern.

“Do you care if I write in the vernacular?” he asked his teacher. “You know, I talk like ‘F*** you,’ ‘Screw this,’ Screw that,’”

After getting the green light, Bill gave his professor his first paper.

“Is any of this true?” Bowers asked. “All true,” O’Connor said.

Recognizing Bill’s ability, Bowers took O’Connor aside and told him to ignore any assignments he gave the rest of the class and just continue with his narrative.

“At that moment, I found my fucking voice—gambling, whores, alcohol, drugs, insanity—the things I’ve done all my life,” he says.

He says he also found God, although it took awhile, and not exactly in the conventional sort of way.


“I don’t want to be one of those fucking guys—you know—the…I did it—don’t you do it — I’ve-found-God assholes,” O’Connor says.

“Billy Graham says that God talks to him and apparently Billy introduced God to his son because now his son is carrying on the multi-million dollar business,” he says.

“It’s just that, against all odds, I’m still here and I feel maybe I’m meant to help others by telling my story.”

Now in his senior year at the University of Florida, he asked his journalism professor Mike Foley what he should do with his material. Foley told him it was too good to give away. He also encouraged him to write in the narrative style.

O’Connor has already written 26 chapters of a would-be book loosely based on his life as a firefighter all the way through 9/11, as well as his life as a bookie, but realizing that his strength is dialogue, he’s now thinking about writing a screenplay instead. And he has some Hollywood connections.

He says he just got off the phone with Jack McGee last week, a television and film actor, probably most known for his role as Chief Jerry Reilly on the television series “Rescue Me” that ran for three seasons on FX. Jerry was O’Connor’s engine chauffer when Bill was a lieutenant for the NYFD. Jerry told Bill he would show his screenplay to Mark Wahlberg, who played Jerry’s son Micky Ward in the recent critically, acclaimed film “The Fighter.”

In addition to that connection, Bill’s says his ex-wife’s uncle is the president of Paramount Pictures.

“This summer I’m sequestering myself,” Bill says. “I’m going to write this fucking screenplay and turn up bodies and billions of dollars.”

Only four weeks away from graduating, he wants to get his B.S., although he doubts he will ever use it. His last journalism core classes this semester include ethics and law.

“Ethics: It’s too late in the game for me,” he laughs. “And the only thing I know about law is skirting it.”

O’Connor got together with Mary Kate, his current girlfriend of 15 years when he was 47 and she was 24. She thought that perhaps over time that he would get too old for her, but now at 40, she sees him hanging out with classmates who are barely half her age.

“When we first got together, I was afraid that his friends were so much older, but now I think I am outgrowing him,” Mary Kate says.

“His friends are always calling him up, asking him to play video games with them,” she says.

“I don’t go,” O’Connor says. “Even fucking Pacman was too far in the future for me.”

Although his spirit is young, O’Connor is conscious of his age enough to consider he might not have a lot of time to do all the writing he wants to do. He is also philosophical and light-hearted about his chances at success.

“If nothing comes of this—so what!” he says. “It’s a hell of a lot better than playing golf.”

Bill currently lives near Phoenix, Arizona where he is a regular on the comedy club circuit. He has written two critically acclaimed weekly columns, two screenplays, a number of thought-provoking political pieces, and is now set to publish his book that Jack Kerouac’s former editor and rock biographer Ellis Amburn has called “Raw, fresh and ballsy, eminently readable.” And if that’s not enough, he recently finished third out of almost 800 contestants in Arizona’s Funniest Comic Contest.

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