Waingro’s Wines: or How, After a Lonesome Stay in Folsom Prison, an Ex-Heister Tried to Live, Laugh, and Love in Napa Valley

By Matthew Kasper and Mike Itaya

After Michael Mann’s Heat 

You know that feeling, when you go into the prison cafe for chow, and everyone has a lunchtime friend-dude? Everyone’s already jawing it up and you’re stuck holding a tray of potato salad? I’m Waingro: combined first name and last. A living, breathing, compound noun. Though, I’ve always been a simple man. I get in trouble trying to be more than what I am. 

It’s like the red-hot caper I pulled back in ‘95. I was rolling with a high-line crew of bonafide baddies, brand new besties, taking down scores, eating Cheesaritos with the best of them. 

Looking back, it was the highest time of my life (and not just because of the coke either). 

But. 

My crooked-ass crew of confederates tried to whack me in a Taco Bell parking lot. The details of what happened next, I won’t go into. A boatload of people died. I got sent to the pokey. And, yes, there is an interpretation of events that places blame squarely at my door. But all that’s in the wretched past. 

The day of my parole, I decided to find a dude entourage, but this time really upped my friendship game. I took my jailhouse blues and a Megabus ticket to Napa Valley, because sometimes a man needs a palliative pinot to wash away the worries of this sorry world.

Inside Robert Mondavi Winery, I saw this squad of dudes all batched up, pre-wedding. I decided to make them my new-new besties. “You boys look like you’re ready to have yourselves a good time,” I boomed. “I’m rolling with ya now!” None of the men looked thrilled, but I could tell they were afraid to say anything. And sure enough, as soon as we all got our first pours–an anxious process that had them all fiddling with phones and their Oakleys while also looking for the exit–I raised my glass. “Live. Laugh. Love.” Three of them winced.

Hoping to cut the tension, I busted out some vino knowledge I’d learned from a junkie toilet wine-vintner in the hoosegow: “The grape’s journey, as it were,” I expounded, filling the painful, but as yet, violence free, silence, “makes it fruit forward. Would you say it hijacks all those other earthy flavors?”

Our sommelier, eyebrows raised as high as they could go, turned away in embarrassment. A rando standing next to me made a sound somewhere between a cough and a sneeze. 

I suppose you will have by this point guessed what came of my newfound bros at Robert Mondavi Winery–that they, like my credit score, my women, my luck overall, ran out on me, left me standing at the bar with the bill. I stared down into my wine, with nowhere to go, and no one to see when I got there. In the end, I suppose it was the tannins in my glass that reminded me so much of the lonely bitterness I’d known all my life. 

About the Authors

Matthew Kasper lives in Baltimore. He has an MFA in Fiction from Pacific

University. His work has appeared in Newsweek, Halfway Down the Stairs, Quarterly Literary Review Singapore, and elsewhere. He loves Heat.

Mike Itaya is the editor-in-chief of DIRTBAG and writes about dirtbags, always.