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Fifty years ago, Jonathan Sheppard bought four yearlings at the Fasig-Tipton yearling sales at Saratoga. And changed racing. Then in his early days as a trainer, he had never really purchased a yearling – let alone traded bids among racing’s big names.

But there he was, backed by an owner just getting started as well.

“I was training a few horses for George Strawbridge then, mostly steeplechasers and some he rode himself,” said Sheppard in 2008. “He said we ought to buy some yearlings at Saratoga and gave me a $100,000 budget. We bought four.”

Sheppard sounded amazed when he talked about it 13 years ago, and somewhat the same when I spoke to him from his home in Florida Monday.

“It might have been the first time I ever bought a yearling,” said the Hall of Fame trainer, who retired after the 2020 season. “It was his idea. We just went to the sale and shopped.”

They bought Hip 48 first. Bred in Virginia by Keswick Farm, the daughter of First Landing sold late on the first night (Tuesday, Aug. 10). Sheppard and Strawbridge came right back to buy Hip 49, a colt by Crème de la Crème bred in California by Verne Winchell Jr. Three nights later, they added Hip 212, a Flag Raiser colt from the liquidation of Bieber-Jacobs Stable and finished off with Hip 221, a Maryland-bred Northern Dancer colt from Windfields Farm.

Sheppard went $1,500 over budget, but Strawbridge would have no complaints. The quartet (with purchase prices) turned out to be:

  • • Fast Approach ($39,000), one of Strawbridge’s foundation broodmares who produced Grade 1 winner First Approach, Grade 2 winner Last Approach, Grade 3 winner Summer Fling, and six other winners.
  • • Cafe Prince ($17,000), a two-time Eclipse Award winner as champion steeplechaser and member of racing’s Hall of Fame.
  • • Social Conscience ($10,500), a steeplechase winner and foxhunter at Augustin for years.
  • • Northern Fling ($35,000), a graded stakes winner on the flat and sire.

All great achievements have a catalyst, and that was probably it in Sheppard’s Hall of Fame career. He’d trained winners to that point, won his first National Steeplechase Association training title in 1970 but nobody would have pegged him for a career spanning 56 years, 3,426 wins, champions on the flat and over jumps and so on.

Sheppard won 26 NSA training titles, the last coming in a Covid-shortened 2020. He won just about every important American jump race, including Saratoga’s New York Turf Writers Cup a record 15 times. After his retirement, NYRA renamed the Turf Writers for him and the race has its first running today. He won’t be here to present the trophy, but he’ll be watching.

“You usually have to wait until you die to get a raced named for you,” he said Monday with a cackle. “I’m flattered. I don’t watch much racing, but absolutely I’ll watch on Wednesday.”

Sheppard spent much of 2020 in Florida due to the coronavirus pandemic, guiding the stable to 20 jump wins (and 19 more on the flat) through assistant Keri Brion, and stayed there with wife Cathy after the retirement announcement in January.

“It’s very peaceful,” he said of the change. “We’re happily living in our nice house in Florida, just enjoying the good life.”

His impact on today’s race is heavy. He trained three of the eight entries – Baltimore Bucko, French Light and A Silent Player. Two trainers, Brion and Leslie Young, worked for him, with Young leasing his former training facility for her stable this year. Trainer Ricky Hendriks rode races for Sheppard.

Sheppard won his first Turf Writers in 1979, with Leaping Frog, added wins in 1983 with Double Reefed and 1984 with Flatterer. Double Bill and Yaw won four in a row from 1989-1992. Mistico defeated champions Lonesome Glory and Warm Spell, when all three carried 168 pounds, in the rain in 1994. Bisbalense upset the 1997 running. Ninepins turned back time to win at age 13 in 2000. It’s A Giggle knocked off heavy favorite Praise The Prince in 2001 to go 3-for-3 at the meet. Mixed Up came through in 2006, Sermon Of Love in 2010. Italian Wedding flew Sheppard’s silks in 2013. And Winston C completed the rare A.P. Smithwick-Turf Writers double in 2019.

Asked his favorite, he hesitated, then landed on Flatterer – the homebred Hall of Famer, four-time champion and world-traveler.

“I suppose Flatterer would have to be a standout,” Sheppard said. “He was a great horse and I co-owned and bred him so that added to it. He had to do it the hard way, carrying weight and as the favorite most of the time. He had a tremendous record, and to have bred him made it extra special. He was able to win the long-distance races we had like the Colonial Cup (2 3/4 miles), and was quick enough to win at Saratoga too.”

A year after his Turf Writers win, Flatterer was so good that no one would run against him. NYRA carded the stakes as a 2-mile turf race at Belmont Park. Flatterer ran anyway and finished third behind Rokeby Stable’s Bobby Burns.

Monday’s phone conversation was short, and would have felt far more natural in Sheppard’s tack room at the Oklahoma Annex.

I asked him one more question, “What kind of horse does it take to win the Turf Writers, er, Sheppard?”

“It’s a good test, it’s run on the flat track and because of that it’s a speed course but it’s a stamina test too because it’s a little bit longer than some of the other races at the flat tracks,” he said. “It takes a speed horse who can carry his speed, I suppose.”

He would know.