A regular rider provided a cash retainer just at a time when it was needed. (Shutterstock)

A regular rider provided a cash retainer just at a time when it was needed. (Shutterstock)

An offer in dollars too good to resist

Expenses get covered in what feels like a deal with the devil


When I first started driving a taxi, there were still traces of the old days around. On the streets, a camaraderie existed among most cab drivers. Even though the industry was in a freefall, you could still make money. Not like in the past, according to the old-timers, but enough, it seemed, to keep us coming back to the yard for another shift.

Over the next year, though, lots of familiar faces began to disappear. The drivers I used to see at cabstands and queued outside theaters and late-night dance clubs weren’t around anymore.

By the summer of 2016, the streets were as lonely as my backseat. Working four shifts each week, I was struggling to bring home more than $100 a night. Which didn’t come close to paying all the bills. And now that my wife was pregnant, so much more was at stake. Fortunately, she had plenty of freelance work, but once the baby arrived, I would have to cover the gaps.

Around this time, I was having a dreadfully slow shift one night, chasing ghosts on Market Street, prowling through the Castro and the Mission, looking for anyone to get in the back of my cab…

Just as I’m about to descend into complete despair, my phone chirps. It’s Mr. Judy. He’s at Lucky and wants a ride home. That’s a $20 fare. I stretch and say I’m just around the corner, then race across town before he gets tired of waiting.

After picking him up that first time and giving him my number, he started calling for rides almost daily. When things were busy downtown, I’d blow him off. But there were some nights he’d need more cab rides than half The City combined. And he was always generous. Not only paying the meter, but usually doubling it. Part of what he called profit sharing.

As I pull up to the bar, he’s standing outside talking to the doorman.

“Sorry,” I stammer. “The lights were brutal.”

Taking his preferred route to the flop house in Bernal where he’s been staying the past few weeks, he asks me about my night. Usually, he just babbles the whole way, but tonight, he’s practically fully cognizant.

I tell him about my night, how I barely have my gate and gas and that I’ll have to work late to make any kind of profit.

“How much is your – what do you call it, your gate?” he asks.

“Yeah, my gate is $105 tonight,” I tell him. “But I also have to put $15 of gas in the tank. Plus, a $5 tip for the cashier. So, more like $125.”

“Damn. And that’s all you’ve made so far tonight?”

“Pretty much.”

“Here.” He pulls out a wad of bills from his front pocket. “I just keep shoving moving in my pockets all night and never get a chance to sort it out,” he says with a nervous chuckle. He takes seven 20s out of the mess of cash and hands them to me. “Take this and go home to your wife. There’s nothing left out here tonight. The bars are dead. Just go home.”

The next day, Judy calls me for a ride in the early afternoon, just as I’m leaving the National yard. I pick him up outside Casanova. On the way to Lucky, after a few stops along the way, he brings up my gate again.

“I have something for you.” He hands me a folded stack of bills. “That’s $140.”

“What’s this for?”

“It’s like a retainer,” he says. “I usually take several cabs each day. But I’d rather only deal with you, since I can trust you. So, if you can be available to pick me up regularly, I’ll cover your gate.”


“And pay the meter, too, of course.”

Unsure if he’ll even remember this offer later, I accept his offer. How could I not?

After dropping him off, I head downtown to try my luck in the Financial. There’s something a little nefarious about this proposition. It feels like I’m making a deal with the devil. But with my expenses covered at the start of each shift, I have one less thing to worry around. For now, at least.

Kelly Dessaint is a San Francisco taxi driver, currently on hiatus due to COVID restrictions.

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