Taylor Made Farm + True.Ink Present

"In this game you pick more losers than winners, but you hope the winners count."

We never thought we’d buy a racehorse in the checkout line of a supermarket,  especially after our magazine’s credit card was declined, but that’s how it happened.


We were in Saratoga Springs, in upstate New York, and had come from the Spa, the oldest racetrack in the country, about to fire up a late-summer barbecue of shrimp kebabs, corn, and beer.

We tried the card again. No luck. 

The guy behind us was annoyed. Not annoyed. Angry. 

He looked familiar, though. Big guy, small glasses. We had seen him earlier that day in the paddock, the private area at the race track reserved for owners and trainers, and where the horses get saddled up before each race. 

After the third denial, his frustration turned to pity and he asked us why we were in town. We were looking for a story about a racehorse, we said, and then he softened even more. He ushered us into some patio chairs by the vending machines to share his tale. 

“Nobody really knows my name,” he said. “They don’t call me the Wizard. They don’t call me Michael. They just call me Wiz.” 

He had a rakish smile and wore a polo shirt, the gold chain of a necklace peeking through the open collar. He was a writer also, he said, though with a singular expertise. 

“There’s stockbrokers that pick stocks for people,” he explained. “I pick horses. People bet their money on what I have to say.” 

Wiz’s real name was Michael Kipness, and he was a handicapper. But after decades offering betting advice, his method of picking horses was on the verge of extinction. Once, he sold his picks outside the track on a printed piece of paper called a sheet. Now, getting into retirement age, he struggled to find an audience on the Web, and had made a late-career pivot. He was trying to cash in on a lifetime of horse-racing intelligence and compete with the wealthy elite in the sport by buying and racing his own horses. 

So far, the move had been a disaster, he said. Then he invited us back to the summer home he’d rented, promising to reveal all the mysterious things that had gone wrong with Ven Holiday, his favorite horse.



We were in Saratoga Springs, in upstate New York, and had come from the Spa, the oldest racetrack in the country, about to fire up a late-summer barbecue of shrimp kebabs, corn, and beer.

We tried the card again. No luck. 

The guy behind us was annoyed. Not annoyed. Angry. 

He looked familiar, though. Big guy, small glasses. We had seen him earlier that day in the paddock, the private area at the race track reserved for owners and trainers, and where the horses get saddled up before each race. 

After the third denial, his frustration turned to pity and he asked us why we were in town. We were looking for a story about a racehorse, we said, and then he softened even more. He ushered us into some patio chairs by the vending machines to share his tale. 

“Nobody really knows my name,” he said. “They don’t call me the Wizard. They don’t call me Michael. They just call me Wiz.” 

He had a rakish smile and wore a polo shirt, the gold chain of a necklace peeking through the open collar. He was a writer also, he said, though with a singular expertise. 

“There’s stockbrokers that pick stocks for people,” he explained. “I pick horses. People bet their money on what I have to say.” 

Wiz’s real name was Michael Kipness, and he was a handicapper. But after decades offering betting advice, his method of picking horses was on the verge of extinction. Once, he sold his picks outside the track on a printed piece of paper called a sheet. Now, getting into retirement age, he struggled to find an audience on the Web, and had made a late-career pivot. He was trying to cash in on a lifetime of horse-racing intelligence and compete with the wealthy elite in the sport by buying and racing his own horses. 

So far, the move had been a disaster, he said. Then he invited us back to the summer home he’d rented, promising to reveal all the mysterious things that had gone wrong with Ven Holiday, his favorite horse.


The Wiz’s summer residence was a modest house a few miles from the track entrance. He’d been living here for the racing season in solitude, cooking himself chicken cutlets and waking at dawn to make his picks. He refused to go to bars, avoided restaurants.“I’m like the Wizard of Oz,” he would tell us later. “I don’t come out into humanity very often.”

We uncorked a bottle and listened to his story. There was Red, the handicapper so good he got banned from the track and fingered as a Russian spy. The Wiz became his apprentice, cutting high-school classes to help Red clean up at the Pennsylvania and Maryland tracks that didn’t know him. There was Willie the Doorman, technically Wiz’s first bookie, though the Wiz was handicapping races for him too during his teens.

And of course there was Papa Wiz, who introduced his son to the track. “My father used to say, ‘If I took my son to the movies as much as I took him to the racetrack, he would’ve been an actor.’” Papa Wiz called the racetrack “the open-air synagogue,” and the rabbis he worshipped were gamblers, trainers and horse owners who came home with big money.

The Wiz grew up on the Upper West Side, grittier in those days, and he treated his walk to the newsstand for that day’s racing form like a ritual. The other gamblers hanging around started to notice, realized this kid had a thing for numbers and an unusual horse fixation. They’d bug him for picks, ask him his secrets, but the Wiz would already be walking off with his face buried in stats.

As an adult, Kipness surrounded himself with characters — friends he would never have to address by real names. There was Pippi, his accountant, and Source, a wheelchair-bound prodigy for horse picks who reported to him from a sports book in Vegas, and The Matzo Man (“Matzo” for short), the owner of the Streit’s Matzo factory on the Lower East Side. Even the Wiz’s house here was a refuge for friends like Frankie Big Balls, who checked in at Chez Wiz for the weekend with his girlfriend. Frankie earned his nickname for stamina in the bedroom.

“You can hear it through the whole house when those two are here,” Kipness said.And there was Joey. Joey Russo, the only character in Kipness’s stable without a nickname, at least to Wiz. Russo was a horse trainer.

“They called him, ‘The Bettor’s Best Friend,’” Kipness said. “He was great. In the nineties, Joey was almost the leading trainer in New Jersey, starting so many less horses. They always paid good money. Joey’s win percentage is tremendous.”

But Russo’s career took an unforeseen turn.

“He got sick, then his wife got sick, and Joey had no horses,” Kipness said.

She was diagnosed with ovarian cancer; he was diagnosed with throat cancer. They both underwent treatments. Russo could no longer make it to the barn each morning.

Ven Holiday was set up to be Russo’s comeback horse.

“He’s young, he’s got upside,” Kipness said of Ven Holiday. “A horse that has the ingredients for success.”

Ven Holiday also had good genes. His father was Harlan’s Holiday, the great closer. Harlan’s Holiday was an odds-on favorite at the Kentucky Derby who won millions in prize money. He thrilled fans with his driving, come-from-behind surges down the home stretch.