Surprised to find David Milch’s memoir LIFE’S WORK in an obscure bookstore here in Thailand. It’s about his television-writing career, creative process and personal demons.

You might remember Milch for the popular television dramas he wrote or created, including HILL STREET BLUES, NYPD BLUE, DEADWOOD and LUCK, the series about horse racing. You also might know him as the owner of Breeder’s Cup winners GILDED TIME and VAL ROYAL. I used to see him at Santa Anita and the 53rd St. OTB Teletheater in Manhattan years ago.

LIFE’S WORK is a fascinating read, but it left me sad. For one thing, how and why did a brilliant and accomplished guy like Milch have serious substance abuse issues? Specifically, I was hoping to read how that started for him. The initial impulse to try. Wasn’t there a voice in his head that said stop? The answers weren’t there.

Then I learned he developed Alzheimer's, which in and of itself is saddening. And finally, the shocking bombshell that, unbeknownst to his wife, he gambled away his considerable fortune and beyond. How could this happen?

There’s a moment in THE HUSTLER when “Fast Eddie" Felson, in his first pool game against Minnesota Fats, is losing badly. Suddenly, his partner flat-out tells Eddie: “Stop. He’s too good!” There’s a moment in our gambling lives when we instinctively know when to fold. When I’ve had bad days at the track (usually after good days?), there was a voice inside telling me to stop, take a break and reset. I’ve always listened to that voice. But, of course, not all people can.

I was watching CNBC’s Fast Money one memorable afternoon at the tail end of Covid-19, when the inimitable Dave Portnoy came on to discuss his experience as a day-trader, trading the stock market from home. Essentially, Portnoy related how he lost, lost and lost. He zigged when he should’ve zagged. Went short at the wrong time. Bought at the wrong time. He blew a huge chunk of money very quickly. Meanwhile, did the CNBC hosts express any warning to Portnoy or their audience about the downside of day-trading? The perils of gambling like this? No! They smiled and laughed all through the interview. To them, it was all so cute: Little Dave and his pizza-review world, now gambling stocks! Haha! On the other hand, every intelligent person watching at home was saying to themselves: “Dave, you’re pissing it away! Don’t be a fool. STOP!”

Many years ago at the former Gulf & Western Building off Central Park, I met an odd but interesting fellow named James Toback, a filmmaker, now of dubious notoriety. I told him the movie he had written, THE GAMBLER (1978) with James Caan, was a favorite of mine. At this, he lit up and we ended up walking across the park together, talking movies. Perhaps he saw me as a fish who could invest in his next project.

Fast forward to my typical weekday lunch in the 1990’s, gambling horses at the 53rd St. Teletheater in Manhattan. Joe Torre and Don Zimmer at a nearby table. At the betting windows, I’m second in line behind a guy in a disheveled oversized raincoat, even though it’s a beautiful warm day outside, not a cloud in the sky. The guy just keeps on betting endlessly! Every play having the air of being made up hastily on the fly. No sheets involved. No speed figures. Everything pure serendipity. He’d turn the pages of his flimsy in-house track program back and forth between races and venues, think for a few seconds, dictate to the teller his off the cuff plays… and then repeat. He wasn’t betting the Belmont thoroughbreds. He was betting the harness ovals, some to run later that night. Bathtubs like Monticello, Freehold, Yonkers and beyond. Losersville. I stood there, amazed at the costly wild stabs he made. Finally, I tapped him on the shoulder and told him there were others behind in line hoping to make a bet. Whereupon the guy turned around and said “I’m gonna be a while!” It was Toback.

Maybe I’m wrong. Maybe Toback’s mad ramblings ultimately yielded him huge profits. But I doubt it. Given the self-destructive themes of Toback’s THE GAMBLER, I’ve tried to make sense of it, but still find it mysterious to understand. In any case, the point is: He didn’t know when to stop.