When Hall of Fame trainer Robert Tiller reaches the 2,000 career-win mark, it will no doubt leave him feeling tickled pink.

While his name is often, and understandably, associated with Pink Lloyd, one of the greatest sprinters in Canadian Thoroughbred history, the man who campaigns the multiple stakes champion is more than just a one-horse wonder.

Much more, in fact.

With 1,998 wins to his name, Tiller, who launched his horse racing career over 54 years ago, is still very much at the top of his game, as meticulous and motivated as he has ever been.

He’s also busy.

Heading into the 2020 Woodbine Thoroughbred campaign, which now has a starting date of June 6, due to the COVID-19 pandemic, Tiller has 45 horses in his barn.

He’s readying his charges for what he hopes will be another productive year at the Toronto oval.

And while his main focus is mapping out winning strategies for each horse in Barn 36 on the Woodbine backstretch, Tiller found a few moments to reflect on a career that spans six decades.

At 15, Tiller began his life in horse racing, walking hots. His training career started in 1972.

When he won 21 races from 89 starts as a rookie, others quickly took notice.

The early success earned him accolades as well as a nickname.

“They called me ‘Wonderboy’ for a while,” said Tiller, who won his first race with Royal Greek Ship. “And then I became ‘Wonder-something else.’”

In 1975, his Near the High Sea, a 53-1 longshot in the Queen’s Plate, finished second behind favourite and future Canadian Horse Racing Hall of Fame inductee, L’Enjoleur.

If there were questions about Tiller’s odds to be a long-term success story, he answered them with consistent trips to winner’s circle year after year.

He’s won 60 or more races on eight occasions, and was Woodbine’s leading trainer in 1994, 1997, 2001 and 2003, the year his horses earned just over $4 million.

Initially known for his astute claiming abilities, Tiller, over time, developed an eye for seeking out and acquiring inexpensive yearlings, and coaching them to become top talents.

His Sovereign Award winners include Rare Friends, a multiple stakes winner and top two-year-old colt in 2001, Simply Lovely, the top two-year-old filly of 2004 and Win City, Horse of the Year in 2001 and champion three-year-old colt with triumphs in the Prince of Wales, Queenston, Marine, Plate Trial, Col. McLaughlin Stakes and Autumn Handicap.

Other notable Tiller trainees include Domasca Dan, Elated Guy, Talk Back, Brass in Pocket, Winter Garden, Forever Grand, Twisted Wit, Cheap Talk, Top Ten List, Are You Serious, Spread The News, Midnight Shadow, Dancer’s Bajan and Dave The Knave, who delivered him his 100th career stakes victory.

Tiller is a three-time Sovereign Award winner himself, earning top trainer recognition in 2001, 2003 and 2004.

Consistency has been the hallmark of a highlight-laden career that also includes induction into the Canadian Horse Racing Hall of Fame, in 2008.

A big reason behind the many accomplishments has been, in Tiller’s own words, attention to the small details. It’s an approach he put into practice early in his career.

“Lou [trainer, Cavalaris], he was a very good horseman, probably one of the greatest trainers we’ve had here, in my opinion, and he liked me. He told me, ‘Everybody trains horses, but it’s a game of details… that’s the difference.’ I tried not to forget that over the 54 years I’ve been here.”

Now 70, Tiller isn’t quite ready to call it a day. “Most people my age are enjoying their retirement, or they’re in a rocking chair. Or maybe they aren’t enjoying their retirement at all. But I’m still here, and I have a lot of horses to take care of. I guess they won’t take me alive. I’ve been lucky in a lot of ways. I’ve met a lot of great people, had a lot of great years, had a lot of great owners, and a lot of great horses.”

Pink Lloyd, an Ontario-bred son of Old Forester, is no doubt the top horse Tiller has campaigned.

Owned by Entourage Stable, the chestnut has won 22 of 27 starts. In 2017, the gelding, undefeated in eight starts, delivered his connections three Sovereign Awards, including Canadian Horse of the Year honours. In 2018, he extended his win streak to 11 with victories in the Jacques Cartier, New Providence and Achievement Stakes. At season’s end, he was named Canada’s champion sprinter.

In May, Pink Lloyd was voted top male sprinter for the third straight year. Unbeaten in six stakes starts in 2019, he also won his second Sovereign as champion older male main-track runner.

“I’ve had a lot of great horses over the years, and won some really nice races. Pink Lloyd is the gem of all gems. He’s eight years old, and he’s just like me… he’s getting old. I think he’s really doing well right now. This will probably be his last year. As they say, all good things must come to an end. As long as he’s okay, he’s going to go to LongRun [Thoroughbred Retirement Society], and live his life there.

“But we’re not looking at that right now. He’s doing great. He’s had little injuries here and there, and then you think it’s all over, but he keeps bouncing back. He has a big spot in my heart. I absolutely love him and I’ll never forget him. He’s an icon. I’m not a guy who is left speechless, but he’s done that for me.”

It would no doubt be fitting to have Pink Lloyd [Michelle Gibson is his groom] deliver Tiller his 2,000th win.

Whatever horse does deliver the milestone moment, it will be one more cherished highlight to add to a lengthy list of successes.

“It’s a great accomplishment because 95 per cent of the wins have come at Woodbine. I didn’t go year-round, maybe just a few in the early days. I’ve won races at Saratoga, I’ve won races at Aqueduct, and I’ve won races at Belmont. Those 2,000 wins will have been done over many years, but only racing on the average of nine or 10 months out of the year. And it’s right here at Woodbine. I’m proud of that. It’s wonderful. The only sad part is that I’ll be social distancing when it happens. But it warms my heart.”

As it does for those who work in his barn.

Tom Lottridge has been Tiller’s assistant trainer for 35 years.

“Bob is successful because he’s hands-on, and he knows all his horses, and every horse in detail,” said Lottridge. “The horses talk to him – it’s amazing. It’s an honour to know him. I’ve been with him a long time and he still amazes me.”

The last word goes to Tiller.

“I’ve always been honest with my owners and the regulators. I’ve always been good to my [staff], which is very important to me. I’ve had very loyal people and I’ve been loyal to them. At the end of the day, I have no regrets. My career, it will come to a bit of a simmer over the next few years. But we’ll just see how it goes.”

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