Editor’s Note: Saratoga Race Course runs the first edition of the Leo O’Brien Stakes Sunday (post time 1:10 p.m. One of the last times someone from The Special interviewed him, he talked about what it was like to gallop champion 2-year-old of 1970 Hoist The Flag. From the Aug. 6, 2019 edition of The Saratoga Special.
It’s early spring, maybe late winter at Virginia’s Middleburg Training Center and Sidney Watters Jr. puts together a set of 2-year-olds.
Tom Skiffington puts his tack on one. Colum O’Brien heads for another. The third, the biggest, gets a special request.
“You’re the biggest rider, get up on the big guy,” Watters says to Leo O’Brien, Colum’s somewhat larger brother. Leo does as he’s told and then tries to follow instructions once out on the track. Watters wants them to gallop, then pick up the pace over the final quarter mile. It’s early days, but it’s also time for a test. Who’s fast? Who’s competitive? Who’s worthy of joining the string in New York for a juvenile campaign?
The two smaller colts are quicker, more agile, and outrun Leo and his mount for the first mile. When it’s time to quicken up, they sprint away again. Then Leo feels it, the colt finds his stride, catches up to himself, accelerates and passes his two mates while galloping out. Leo pulls him up, feels proud, figures Watters will be delighted.
“Where is he?” the rider asks himself as they go past the trackside clockers’ stand. Watters was waiting back at the barn.
“If he can’t beat those horses, he’s useless,” Watters barks.
“Wait a second,” Leo sputters, Irish brogue put to the test. “You didn’t see. This horse can fly. It might take him a little while to get going, but he can really run. Believe me.”
In time, Watters and everyone else believed.
The big colt was Hoist The Flag. By year’s end he’d be champion 2-year-old colt of 1970, undefeated in four starts (with one debatable disqualification), and the favorite for the 1971 Kentucky Derby.
And it all started at Saratoga 50 years ago. By Tom Rolfe out of the War Admiral mare Wavy Navy, the bay colt joined five others in the 1969 consignment of John Gaines and James Houlahan in Barn 7B. They sold on the last of four nights. Bred by John Schiff, Hoist The Flag was Hip 203. He had people talking, though some of the chatter was about a bruised eye. Watters, bidding for Mr. and Mrs. Stephen C. Clark Jr., went to $37,000 to prevail over George Poole who was bidding for Sonny Whitney.
Fasig-Tipton bid spotter and auctioneer Steve Dance was there.
“Sidney Watters,” he said Monday morning, going full Maryland where the last name sounds more like Wooders. “OK, OK, he sat right there on my left with Mr. and Mrs. Clark. They were in the third or fourth row. Right in front or behind them were Mr. and Mrs. Mills, Bert Firestone would have been a little bit further up. In the back row were Mr. and Mrs. Ledyard. I remember Russell Jones jumping up and pointing at somebody trying to bid that nobody saw, but that was probably a different year.”
Dance said it like he was refreshing his memory, and he was, but the point was the 1969 Saratoga sales pavilion was home to racing’s elite just like it is today. From the auctioneers’ stand, Watters and the Clarks sat in the center section – a little bit to the right. Watters landed a racing legend with a raise of his hand that day.
From Middleburg, Hoist The Flag joined Watters at Belmont Park. He made his debut on Sept. 11, 1970 and won by 2 1/2 lengths going 6 furlongs. Twelve days later, he won again – this time by 5 going 6 1/2. Next came the Oct. 1 Cowdin Stakes, where he blitzed 11 others in 1:22 and change. As it does today, the 1-mile Champagne beckoned every good 2-year-old in New York. Sixteen horses showed up and Hoist The Flag drew off to win by 3 lengths at 4-5. The stewards thought otherwise, however, and placed him last for interference early in the $250,000 race. Even today O’Brien scoffs.
“He was outside in a big field and Jean Cruguet went to drop in and one of the stewards said he bothered some horses.”
O’Brien snuck into the film session afterward and listened as the stewards talked to Cruguet and Braulio Baeza about the incident. The stewards explained all that happened, told Cruguet what he should have done differently. Then O’Brien heard Baeza speak.
“I wasn’t fouled, I had no chance. That horse can’t be beaten.”
Hoist The Flag was named champion 2-year-old male, and spent the winter in Camden, S.C. Watters pegged an allowance race at Bowie as the 3-year-old debut in March. Going 6 furlongs, Hoist The Flag was never headed and won by 15 lengths. By then, Colum was the horse’s regular exercise rider, but Leo took a break from the steeplechase circuit and made the trip to Bowie. He was awed, and just a little bit defiant.
“The Clarks wanted me to raise the American flag as he was coming up the stretch, but I was embarrassed,” Leo said. “I didn’t want to do anything like that. Mrs. Clark asked me. I was like, ‘OK.’ We were at Bowie and I was standing on the ground by the wire. He was 10 lengths in front and I raised it. I hoisted the flag. They got a kick out of that.”
At Aqueduct eight days later, Hoist The Flag made easy work of the Bay Shore – winning by 7 lengths, fouling nobody and consuming all the early Triple Crown talk. Ten days later, it all came crashing down. On March 30, Hoist The Flag broke his right hind leg just after a 5-furlong workout on the Belmont Park training track.
“I was in Virginia and I just remember everybody crying,” said Leo, who won 137 races as an American jump jockey and later trained Saratoga legend Fourstardave among others. “It was terrible.”
Hoist The Flag lived through the injury and subsequent surgery, and became a sire at Claiborne Farm. Among his sons and daughters were dual Arc de Triomphe winner Alleged and champion 2-year-old filly Sensational. As a broodmare sire, he is responsible for Personal Ensign, Broad Brush and Cryptoclearance. He died in 1980 and is buried at Claiborne. His mark on the breed was powerful, though it might have been more.
“The horse would have won the Derby, all those races,” said O’Brien. “Nobody could beat him. He was a super horse, 16.2, good-sized, no bad habits, great horse to ride, really and truly.”
As it does with many of its star graduates, Fasig-Tipton gave Hoist The Flag a plaque above his Saratoga home in 1969. It adorns Stall 28 in Barn 7B, home to the Taylor Made Sales yearlings. A Pioneerof The Nile filly calls it home this week. Monday, she was in the back corner munching hay and waiting for her next showing.
If she felt the significance, she didn’t show it.
For more about O’Brien, who died in January at age 85, see Mid-Atlantic Thoroughbred editorial from February 2026 and a NYRA press office feature from this week.
