My Best Losing Bet

Nothing focused him more than betting. A friend who interviewed with him shortly before Halloween had made a giant squid costume. “Dude, you’re going to bring your costume when you visit and wear it in the office!” he said, and then went around betting everyone that he could make a candidate wear his Halloween costume in the office.

One night at the local dive bar he approached me wild-eyed and asked out of the blue “How much would you bet that I can’t do 30 chin-ups? A dollar? Five dollars?” I looked him up and down. Short. Broad shouldered. Big chested. Solid. About 50 pounds overweight. The frame of a gymnast, hopelessly out of shape and dumpy. I answered “A hundred dollars.”

He looked momentarily stunned. Whatever his expections, this fell outside of them. Then bet-focus overcame him. He had to go forward after that opening. He took the bet.

We spoke the next day in the office. He told me he was able to do two reps. I said he could have three months and three tries. The game was on.

He joined a nearby gym and started going every day. He hired a trainer. He asked at least one gym-rat coworker to join him at the gym and yell at him if he slacked off. He stopped drinking. Gossip flew around the office. How many pounds has he dropped? What is his count up to? Who is his trainer? Who goes with him to the gym?

When the day for his attempt finally arrived he was a changed man. He’d spent $3500 on training. He’d shed 50 pounds. The dumpy form was gone. The inner gymnast had emerged.

A gaggle of about 20 of us walked to a coworker’s nearby apartment. On the way I stopped at the bank to take out cash in case he succeeded. His trainer spotted me. “So you’re the idiot who made the bet.” “We’ll see. Can he do it?” “Oh, you’ll see!”

We crowded into the tiny apartment. A chin-up bar hung in the bedroom doorway. He stripped down to his boxer shorts, jumped up to the bar, and to the chanting count of the crowd performed 31 perfect l-sit chin-ups.

He never looked happier. My handful of twenties would not do. He demanded my inscription on the crisp, newly-minted $100 bill he brought. I gave it gladly.

A short time later I passed on his offer to go double or nothing on 60 one-armed push-ups. I didn’t attend the event, but heard that he pulled a groin on the 53rd rep.

Almost 20 years have passed, yet people still talk about our bet. It’s legendary in a certain crowd. Several years after he won he thanked me for it, saying that it got him out of a rut, into the best shape he’d ever been in, and turned around some things in his life. I want to lose more bets like that.