Breeders’ Cup Presents Connections: ‘If You Work Real Hard, You Get Luckier’

by | 11.15.2018 | 10:49am
Leonard Green (immediate right of the horse) guides Jaywalk into the Winner's Circle after the Juvenile Fillies

Leonard Green is a man of numbers. The top-level accountant spends his days pouring over dollars and cents, but his 30-plus years in the Thoroughbred industry have taught him that it's not all about the dollars; it takes sense.

“Unlike other owners, I'm not in it to drink champagne; it's a business,” Green said. “It's a tough business. It has to be a day-by-day kind of thing, and you've got to be in the right spot.”

Green did take the time to savor his first Breeders' Cup victory at Churchill Downs earlier this month, achieved by a 2-year-old filly his DJ Stable co-owns with Chuck Zacney. Jaywalk, an aptly-named daughter of Cross Traffic, took the lead at the start and never relinquished it in the Juvenile Fillies, crossing the wire a dominating 5 ½-length winner under Joel Rosario.

“This horse is a special deal,” said Green. “It's unnerving how she goes from race to race, how she's traveled from track to track. You think, ‘Okay, where can this horse go from here?' It's exciting.”

Despite the excitement of purchasing and owning a Breeders' Cup winner and achieving success at the highest level of the sport, Green argues his Thoroughbred business plan has not been perfected. He quipped he has yet to win the Kentucky Oaks, or the Kentucky Derby.


As the founder of New Jersey-based The Green Group, an accounting, tax, consulting and advisory firm, and as a college professor, Green knows the value of constant improvement.

“I think I'll stop changing what I'm doing about two weeks after I die,” he laughed. “I've not got it perfect yet. It's a continual process all the time; it's what keeps me young. Both horses and teaching keep me young.”

Early on, Green's racing business strategy focused on the win column, and he achieved a trio of leading owner titles at both Monmouth Park and Parx. He realized victories on the track didn't necessarily equate to wins in the accounting ledger, and his business strategy has been evolving ever since.

Over the course of his career, Green has campaigned Grade 1 winners like Songandaprayer, Do It With Style, and Hoppertunity. His stable currently consists of approximately 100 horses, both broodmares and racehorses. He has a specific strategy when it comes to the yearling sales, involving trainers, bloodstock agents, and the connections created by his tax advisory business, which serves more than 400 Thoroughbred entities.

“We know the business, we know the taxes, so it gives us a real competitive advantage,” said Green. “You have to keep adjusting the business plan the same as you would in a ‘real' business, looking at what is working, what isn't working… I can't only buy the expensive horses because I'd run out of money, so I send out (former trainer and bloodstock agent) Jim McGreevy and (trainer) John Servis to look at all the horses, not the page.”

Green sends his people to appraise the 4,000 yearlings at the Keeneland September sale, for example, and each develops a short list based solely on conformation and physical appearance. His instructions to those agents are to search for more than just the classic-distance dirt profile. The U.S.'s turf racing program is improving significantly, he noted, and sprinters can be undervalued.

Green cross-references those lists and tries to buy the best individuals he can. The partnership with Zacney came about because both owners have horses with Servis, and Green said it continues to work well because they both have a good understanding of how the game works.

A graduate of the Servis/McGreevy analysis, Jaywalk was a $190,000 yearling at Keeneland September; she has rewarded Green and Zacney with more than $1.3 million in earnings.

“John (Servis) is special because it's a lot of trainers who can train,” Green said. “John's that special person where he can see a good horse at the sale. That's where the big investment is, the time and cost-consuming thing. They have to not only know how to train, but how to go to a sale for four or five days… So, yeah, you get lucky sometimes, but I think if you work real hard, you get luckier.”

It's easy to see why Green loves Thoroughbred racing. The industry offers many unique business opportunities, and the passion and excitement of the racetrack is a siren song all its own – it's the ultimate entrepreneurial game.

“You've gotta decide what you're in it for,” Green said. “Sure, the Breeders' Cup was a highlight, but that's not what it's all about – it's about the culmination of a strategy that works.

“Nothing beats strategy, hard work, and surrounding yourself with good people.”

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