The Beard regales Ben with stories before setting him up for defeat.
  • Nick Murway
  • The Beard regales Ben with stories before setting him up for defeat.

As part of my ongoing education in the psyche of Chicago voters, I agreed to play pool against the legendary Freddy “the Beard” Bentivegna, one of the great hustlers of our time.

There’s a connection—just bear with me.

Apparently the Reader needed a mark to get hustled, as part of a video that accompanies a profile of the Beard by staff writer Aimee Levitt .

So on a bright and sunny Friday morning, I headed over to Chris’s Billiards, 4637 N. Milwaukee, which, of course, is dark, dank, and dingy. As pool halls tend to be.

The Beard couldn’t have been nicer.

He regaled me with some outrageous tales about taking fools for their money.

Like the time he hustled the notorious gambler Archie Karas by pretending to be an eccentric, degenerate billionaire. A story he’s told a few times before.

He also reminisced about his nerve-racking showdowns with the late, great Leonard “Bugs” Rucker, who operated out of a pool hall at 63rd and Cottage Grove.

As a special bonus, he told me about Genie, a childhood friend from back in Bridgeport, whose claim to fame was his ability to pee across 26th Street.

Which has nothing to do with pool, but is nonetheless an impressive feat.

As the Beard explained it, the key to any successful hustle is making sure the other guy thinks he’s hustling you. That way you keep him in the game long enough to be skinned.

This is something I know a bit about, having spent the better part of my adult life covering mayors like Daley and Emanuel, who have mastered the trick of hustling Chicagoans into believing they’re getting something for nothing.

As is the case with a certain multibillion-dollar property tax scam where the mayors tell us they’re holding the line on our taxes, even as we pay more and more to the tax man for stupid stuff like this.

But enough about politics. Today’s lesson is about pool. And so we play.

The Beard broke. I figured—a guy this good will run the table. But, no. My turn!

I can’t believe I was so nervous as I lined up to shoot. Hadn’t played pool since my glory days back at the Evanston YMCA in the early 70s.

I missed.

But the Beard still doesn’t run the table.

I got a few more turns. Somehow I made a few. Just like Paul Newman in The Hustler.

Eventually, the Beard put me out of my misery.

“Good job,” he told me. I came away almost thinking—you know, I maybe might beat this guy, if he gave me another game.

In other words, set up like a bowling pin . . .

It’s like when the school board gives the mayor a dime and he gives them a nickel and the board members say, “thanks, boss.”

But I wasn’t going to talk politics.

Masterful hustle, Mr. Bentivegna. You’d have made one helluva mayor—and not just ’cause you come from Bridgeport.