In our previous century, when Baltimore led the league in great characters, you could walk into Dominic M. Leone’s City Hall office and find the councilman kneeling on the floor, dice in hand, cash spread about, engaged in a friendly game of craps.
“Merely conducting the business of the day,” Leone would say, removing a Marlboro from his lower lip to offer a shy smile.
Naturally, the apple not falling far from the family tree, his son, Dominic Jr., grew up to do his own gambling. He became a bookmaker, meaning he took illegal bets on the street number and on various horse races.
Also like his father, Dominic Jr. had political ambitions. He ran for his late dad’s old South Baltimore City Council seat and thought he had a chance to win, until his opponent started some serious campaigning.
This prompted a phone call from Leone one day, complaining of unethical political behavior.
“My opponent,” he cried, “is telling everybody that I’m a bookmaker.”
“But Dom,” I said, “you are a bookmaker.”
“Well, yeah,” Leone agreed, “but he don’t have to tell everybody, does he?”
In those days, bookmaking was considered a crime. Several decades ago, when the state of Maryland discovered you could make serious money at such endeavors, they embraced gambling with such a passion that it sounded like civic duty to place a bet.
These days, you can’t turn on a ballgame without seeing commercials hustling the suckers. We’re deluged before, during and after games. What they used to call a crime is now a state-sanctioned multi-billion-dollar industry.
Gambling’s officially legit. But, class? That’s another matter.
While most of America recently recalled the terrorist attacks of Sept. 11, 2001, some in the gambling industry had their own take on the tragedy. They attempted to cash in on it.
The Boston-based sports betting company DraftKings offered users a 9/11-themed promotion that required three New York teams – the Yankees, Mets and Jets – to win their games on the 22nd anniversary of the attacks, which killed nearly 3,000 Americans and changed the world as we know it.
In solemn hope that they’d make a few bucks on this promotion, DraftKings called their come-on, “Never Forget.”
You want to talk about gambling as a crime? Nobody ever accused a “criminal” bookmaker of being so low-life clueless and classless.
The firestorm on social media, from people offended by the pitch, was so strong that DraftKings withdrew the offer and expressed regrets for its bone-headedness.
“We sincerely apologize for the featured parlay that was shared briefly in commemoration of 9/11,” the company wrote. “We respect the significance of this day for our country and especially for the families of those who were directly affected.”
DraftKings would not say how many people placed bets as a result of the offer. See, that’s part of the problem. It’s not just DraftKings’ hunger for a few extra bucks obliterating all sense of decency.
It’s that they knew it would work. Money is all. It’s not that bettors want to be disrespectful of the 9/11 tragedy. It’s that they heard there was an angle that day: multiple games bundled into a single wager, a shot at nice money.
In the old days, gambling had its limitations. The neighborhood bookie would take any kind of bet, even if it involved loose pocket change. And they weren’t pounding on your door, like those incessant TV spots we see today. You wanted to bet, you called your guy, or you knew where to find him on the street.
For this, the state of Maryland locked up bookmakers, over and over. On the night Cal Ripken Jr. broke the record for consecutive games, the scoreboard at Oriole Park flashed “2,131.”
I felt a tap on my shoulder. It was attorney Richard M. Karceski, who represented the legendary East Baltimore bookmaker Al Isella.
“Hey,” Karceski said, pointing to the scoreboard, “how come they’re flashing the number of times Al’s been arrested?”
He was exaggerating, but not by much. Isella was arrested more than a hundred times for gambling “crimes.” But he never committed one as bad as those guys from DraftKings.

Michael Olesker’s latest book, “Boogie: Life on A Merry-Go-Round,” was recently published by Apprentice House. It’s the life story of Baltimore legend Leonard “Boogie” Weinglass, an original “Diner” guy who grew up to create the Merry-Go-Round clothing chain and contribute millions to charity.
