Odd Job of the Day: Mid-Level Bookies in Cleveland, Ohio

Doug Brown’s profile of two Cleveland bookies named Steve and Luke who run an illegal gambling business together is FASCINATING.

The story covers some background as to how the business operates (you have to have the cash flow to pay out if your whole clientele wins on the same night), the stresses they endure (getting caught, paying out, catching every game, the IRS), and how they built their customer base (“Degenerate gamblers tend to know other degenerate gamblers”).

Not surprisingly, they got into the business as a way to pay down their own crushing gambling debts:

Steve and Luke were $20,000 in debt to bookies when they decided to make a change. You can’t bet your way out of betting debt. All Steve had then was the money from his minimum wage job, student loans and what he borrowed from his unsuspecting family. He cried himself to sleep wondering what he’d have to sell next to dig himself out of the hole he gambled himself into.

“Me and Steve, we both thought we knew more than Vegas so we thought we’d just start betting big with our bookies and then on the side, we just take a little action,” says Luke. “With our bookies, if we lost, we decided we’d just pay that off with the action we were taking in. But we got really, really in the hole with our bookie and Steve was crying a lot.”

Oof. Steve wants to quit the bookie business, and Luke obliged, but in the end he couldn’t bring himself to. Why? Because the job scratches his ‘gambling itch’ so if he quit, he’d just go back to gambling and would be right back where he started.

On the bright side, I have a whole new understanding of what went on in the Sopranos!

Photo: Bob Jagendorf

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