Star jockey wins, then hangs up tack

Gregg Ryan said the thought came to him Saturday morning that it was time to retire.

Gregg Ryan at Old Dominion races Saturday in Ben Venue. Photo by Betsy Burke Parker.

America’s all-time leading amateur steeplechase jockey, Ryan, 50, was feeling fit and healthy as he kissed his wife and toddler son goodbye, then pulled out of his Middleburg driveway for the 45-minute drive to the Old Dominion Hounds Point-to-Point in Rappahannock County.

“I’d always said I’d know when it was time,” said an emotional Ryan, who amassed 150 National Steeplechase Association victories over fences in his 30-year career.

“I knew this was the day I was going to retire. I had great rides [scheduled.] It was a beautiful day. It was one of my favorite courses. It was the right thing to do. I wanted to quit on a good note, not on a stretcher.”

Ryan knows all about injury. In 1994, he broke his back in a crunching fall from Circuit Bar, one of his all-time favorite racehorses. Doctors told him he’d be lucky to walk without pain again, much less ride races.

He had a titanium plate inserted in his lower back during surgery at Johns Hopkins. Against the odds, three months of bed rest and three months of swimming and biking had him back in the saddle in time for fall races.

“Racing is a selfish lifestyle, all about the speed and excitement. You’re sort of a superstar. And I had the bug,” Ryan explained. “I just couldn’t stop. Not back then.”

Steeplechasing is a dangerous sport and Ryan’s final race offered proof.

Fellow jockey Sam Cockburn, 17, fell hard when Otappaz came down over a hurdle with a circuit to go. Cockburn was flung clear and separated his shoulder. Otappaz broke a leg and was humanely destroyed.

“I felt like today was a fitting place to do it. I love racing, but I love my son more,” Ryan said.

Ryan’s day at Old Dominion was successful: he won the amateur hurdle with Devil’s Preacher and finished second in the open hurdle on Dynantonia. He rode Dr. Nitro on the turf for trainer and friend Pete Aylor, finishing fourth.

Ryan, who turned 50 this year, won nearly 350 races — counting both NSA and point-to-point — in a career spanning 1980-2010.

In 2008, he won his 148th amateur race, breaking the longtime mark set by legendary Hall of Famer Rigan McKinney.

Ryan is president of Lee & Mason Financial Services.

He began riding at age 4. He wrestled for St. Lawrence University but locked in on steeplechasing when he graduated in 1981.

One of People magazine’s “most eligible bachelors” in 2001, Ryan married Olympic three-day eventer Linden Weisman in 2007.

“She’s the greatest thing that happened to me,” Ryan said. “That, and John. My focus has just changed now, with my son and family. It was time to quit.

“John’s the greatest,” he continued, speaking of his 20-month-old son. “Being a father just changes your focus. Racing is a very dangerous sport. A lot of it is about ego. Saying that you’re a steeplechase jockey, and are not going to get hurt, is like going out in the rain and saying you’re not going to get wet because you’re going to dodge the raindrops.

“I’m in the insurance business. I know all about risk management.”

Ryan will continue as master of the private Snickersville Hunt, kenneled at his farm in Middleburg, and for the Piedmont Foxhounds.

“There will come a day when I’ll be there to lead John around at the hunt on his pony. I look forward to that.”

“Something just had to give,” Ryan concluded. “I’ve been very successful in life because I’m very determined. I wasn’t going to give up my business. I wasn’t going to give up foxhunting. I certainly wasn’t going to give up my family. It had to be racing. Maybe instead of getting up at 4:30 most mornings to go gallop racehorses before work, maybe I’ll get up and take John fishing.”