End of an Era

Nation’s all-time leading amateur jockey Ryan hangs up tack after Old Dominion victory

By Betsy Burke Parker
Special to the Times-Democrat
Gregg Ryan said it just came to him Saturday morning. Just like that, abruptly – he decided. 
It was a beautiful Easter Saturday. He had three excellent horses lined up to ride at the Old Dominion Hounds Point-to-Point that afternoon. The sun was shining. 
Ryan was feeling fit and healthy, tautly trim for his age, 49, at 150 pounds. He’d kissed his toddler son John goodbye then pulled out of his Middleburg driveway for the 45-minute drive south to the rural Rappahannock County venue west of Warrenton.
Ryan said, amazingly, and for the first time in his 30-year career as a steeplechase jockey, his heart felt heavy. He knew the time had come.
“I’d always said I’d ‘know’ when it was time to retire,” said a tearful Ryan, America’s all-time leading amateur jockey with 150 National Steeplechase Association victories over fences. “I knew as I began my drive that this was the day I would stop. I had great rides (scheduled.) It was a beautiful day. It was one of my favorite courses. But it was the right thing to do. I wanted to quit on a good note, not on a stretcher.”
Ryan knows how dangerous the sport of steeplechasing from experience – in 1994 he broke his back in a crunching fall. Doctors told him he’d be lucky to walk without pain again, much less ride 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.”
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 the races that fall.
Steeplechasing is a dangerous, unforgiving sport – see Ryan’s final race Saturday for proof. Fellow jockey Sam Cockburn, at age 17 his career just beginning, fell hard when Otappaz came down over a hurdle with a circuit to go. The consequences were painful – Cockburn was flung clear and separated his shoulder. Otappaz broke a leg and was humanely destroyed. Cockburn’s own father Bay, Ryan’s good friend and one of the circuit’s best in his day, is in a wheelchair, paralyzed by a training accident in 1998.
At Old Dominion, Ryan 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 on Dr. Nitro, finishing fourth.
Ryan, who turns 50 this year, won nearly 350 races – counting NSA and point-to-point, hurdles, timber and turf – in a career spanning 1980-2010. In 2008, he won his 148th race, breaking the longtime mark set by legendary Hall of Famer Rigan McKinney. McKinney rode from 1929-1939 before going on to a distinguished training career. Speed was in the McKinney blood – son Steve was the first downhill skier to break the 200-kilometer-per-hour (124 miles) barrier. Daughter Tamara was also an Olympic skier and World Cup champion.
Ryan also won several international races – they don’t count in his U.S. lifetime total. He won over hurdles and over the stiff, tall steeplechase fences in the International Jump Jockey Challenge in 1990 and 1992. He won a Fegentri race – an international amateur jockey association – in Holland.
Ryan is president of Lee & Mason Financial Services, a company that offers insurance products to financial institutions nationwide. His late father John was an Army cavalry trooper and an infantry officer officer in the north African and European theaters in World War II. Gregg Ryan began riding at age 4. He wrestled for St. Lawrence University, graduating in 1983. Ryan rode a few races while in college, working with legendary Hall of Fame champion jockey, Warrenton native Jerry Fishback, who schooled him on the finesse and patience required to ride successfully. Fishback trained Ryan’s first winner, Close To Glory.
Ryan’s best racing year was 1991, when he rode 15 winners and was second leading rider on the circuit, professional or amateur.
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 more about how his 20-month-old son influenced his decision. “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 added that his own father had made “a huge impression on my life. It was no decision at all really, choosing (son) John over racing, finally.”
Ryan said he 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.”