Presenting:

Fresh Hoofprints in the Snow

In Brief:

Back from Florida, we discover that racehorse heartbreak doesn’t always happen on the final turn. We look to a historic New York track in the wrong season to set us right. And then we strike out on our own.

This is the third and final part (for now) of our True Stables series. Help us continue the story – check out our fundraiser and sign up for updates (cover © Photopat vintage / Alamy Stock Photo).

Michael Kipness, aka the Wiz, listened to our pitch with his hands clasped like a Talmudic scholar and then rendered his decision.



“You have my word,” he told us. “I’ll sell you a piece of Ven Holiday.”

We had come to his lair: Evergreen Woods, a retirement community outside New Haven, Connecticut, where all that seemed to move was wind through the trees. Unlike an artist who surrounds himself with images for inspiration, or a writer who burrows among books, Kipness is a minimalist gambler, the banal industrial carpeting and radical quiet allowing him to focus more clearly on his daily racing picks. The space is all white, drenched in light, not a poster on the wall, nor any furniture.

Fresh off of witnessing another heroic, come-from-behind charge from Ven Holiday and visiting the Winner’s Circle in South Florida, we had come to see the Wiz with a specific mission: to buy a piece of his horse. The experience of being a horse owner — access to the barn, the nervy morning of the race, the slobber of horse drool on our hands — was a thrill so unique and addictive it was hard to find anywhere else.

We wanted in. We wanted to take a detour from the modern humdrum — laptops, dwindling battery power, endless e-mails — and fall back into the time warp and old-timey pace of the track.

We also wanted to follow Ven Holiday for True.Ink, our magazine, and document the firsthand experience of being a horse owner. In the True tradition of opening up adventures to everyone and living the story firsthand, we could invite our readers to the backstretch to feed the horse, watch the races, and get everyone in the Winner’s Circle photo too.

We didn’t want a large piece of Ven Holiday, nor even a good piece. Just a piece. 

The Wiz agreed. 

And just like that, we had jumped classes. We weren’t editors anymore. We were horse owners. We were part of the story.

Before we signed any papers with the Wiz, we called an expert on horse acquisition to discuss the ramifications of any deal. Ira Finkelstein is a lawyer who has been specializing in horse racing and equine matters for the last three decades. Slight, balding and a steward of thousands of horse dreams, Finkelstein sat us down at a dark law-firm conference table that matched his suit.

He had sober advice regarding our deal with the Wiz.

“Don’t do it,” he said.

Becoming a minority owner in a racehorse, he said, was fraught with complications.

“You have no control. You want control. Where will the horse race?”

Finkelstein asked what level Ven Holiday was racing. 

Claiming races, we told him.

“Well, you definitely don’t want him,” he said. Before the race, any licensed trainer or owner with an account at the track could put in a slip or claim. Once the gates opened, they would become the new owners of that horse. The gamble wasn’t only on winning, but on the horse itself. He told us not to leave anything to chance with a minority stake.

“It’s all about control,” he said. “This way, you can pick the silks. You pick the races. You pick the jockey, and when the horse goes out on the track, it’s the magazine’s horse.”

But what about Ven Holiday? We knew the horse was special. A real closer.

“Don’t worry, there’s plenty of horses out there,” Finkelstein said.

We didn’t want to give up on the Wiz, but before we had the chance, he gave up on us. When we followed up on terms, he complained about paperwork and accounting. When we offered to take on the paperwork, he wanted to think about it. When we offered to finance the accounting, he worried about his other partners.

Meanwhile, Ven Holiday struggled. The Wiz pulled him out of races when he didn’t like the position, then put the horse in tougher races where he struggled to compete. Had the organism returned? Was Ven now on the cheaper medication?

Perhaps Finkelstein was right. We did want control. Ven Holiday was in Florida, too far away for those magical early-morning trips to the barn. Our long-distance relationship with the horse — and his eccentric owner — proved difficult. We had begun meeting with owners who had horses with stronger pedigrees, stabled only a subway ride away. 

We went back to Finkelstein for more advice.

“You really need to own your own horse,” he said.

But how? We didn’t have a credit line big enough to purchase barbecue supplies. How could we afford to buy a decent horse? Let alone stable, train, and race one?

© Littleny | Dreamstime.com – Belmont Race Track Winter 2011 Photo

By now it was winter. Saratoga had been shuttered for months. Ven Holiday was paying us no mind far away in the Florida sun and we were trying to keep the dream alive. Early one Saturday, not long after the biggest blizzard of the year, we made the decision to head out to Belmont Park, hit some new barns and meet some new horses.

Belmont Park is a majestic track, the final leg of the Triple Crown, but really only an empty building and parking lot for most of the year. The trainers enter a different gate, and follow the same path of famous legends like Sunny Fitz and others, part of American history. We drove the winding paths, past run-down barns with strip malls and blocks of drive-thrus and mechanics and convenience stores beyond the fences.

We stopped at intersections as dozens of horses sauntered by, their breath mixing with the car exhaust. Snow covered everything, either untouched or tattooed with hoofprints, no city sludge in sight. The deeper we went, the more the Long Island we knew disappeared.

We parked near a path that some stablehands had shoveled out and met a couple of new horse prospects that day. We had leads on a couple of syndicates, or investment groups with shares for multiple owners. We thought we might hear about an outcast, a horse like Ven we could help resurrect. In a surreal clash of worlds, we even met a trainer willing to trade a share in his own horse for our web-design chops. But the complications, the handshakes, the half-baked deals didn’t feel right anymore.

Worse, none of the horses felt like our own. Maybe it was our Ven hangover, echoes of Finkelstein’s call for control, or something deeper. We didn’t know these horses’ stories, hadn’t seen their struggles, couldn’t parachute into a snowdrift by the tack room with a pocket full of peppermints.

Never buy a racehorse, countless people advised. They still do. But when we went back into the snow that day, picking our way along rows and rows of quiet clapboard, we envisioned what we could build from scratch. Starting with one horse, one wild idea, and a whole lot of fellow dreamers. Are you as crazy we are?

Let’s find out.

Will we end up in the Winner’s Circle? Maybe, just maybe. At the Derby? You can’t rule it out. Wherever we finish, the tale will be epic, and it will be ours. The horse too.

Welcome to True Stables, home of the People’s Horse. We’ve come a long way.

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