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Back when he taught ninth-grade government at Towson High, Gerry Brewster listened to a kid talk about horses.

“I ride eventers, show horses, that kind of thing,” was how the kid put it. 

Brewster had a simple question, “Have you ever heard of the Maryland Hunt Cup?”

“What’s the Maryland Hunt Cup?”




When he recovered from the shock, Brewster took the kid to see the third and 13th fences. “That’s the Maryland Hunt Cup,” said Brewster, who’d ridden in the race four times, semi-regularly started a horse in the race as an owner and carried around a family connection to North America’s oldest jump race going back to 1911. Brewster himself had never won the race, however, and jokingly referred to himself as the “biggest loser” in its history. 

And then even that kid from Towson High surpassed Brewster. 

James Stierhoff gave up eventing, switched to riding jump races and won the Hunt Cup aboard Twill Do in 2010 and 2012 – in a saddle he borrowed from Brewster.

“When he first started riding point-to-points I gave him my old boots and my Bates saddle that I rode with in the Hunt Cup,” said Brewster, who teamed up with Balantic for four tries at the race – a fall, a second, a runout and a fourth from 1985-89. Eventually Stierhoff got his own boots, but kept Brewster’s saddle as a loaner.

“I’m not giving you my saddle, I’m lending it to you,” Brewster told Stierhoff. “When you’re finished with it, you can give it back to me.”

Then the saddle helped Stierhoff produce two Hunt Cup wins and . . . Brewster couldn’t ask for it back. “I cannot possibly take it back from you,” he said. “You won the Hunt Cup in that saddle. I’m giving it to you. It’s now your saddle.”

First run in 1894, the Hunt Cup tends to cultivate history. There are tales of luck, fate, ghosts and such running through almost every race. Surely, Brewster’s generosity would get rewarded by the gods – 

Five years and 11 Hunt Cup starts later, Brewster joined his saddle, student, great-grandfather, grandfather, aunt, two uncles and three cousins as Maryland Hunt Cup winners.


Derwins Prospector upset the $100,000 Hunt Cup as 2016 race winner Senior Senator and seven others failed to finish the 4-mile, 22-fence course in the Worthington Valley near Glyndon April 29. Trained by Joe Davies and co-owned by Adair Bonsal Stifel, the winner outfinished Drift Society (Ire) by three-quarters of a length in 9:46.20. Visiting French amateur Gonzague Cottreau rode Derwins Prospector, who quadrupled his career earnings with the $60,000 payday. 

“There’s a lot of history here so it’s extra special to me,” said Brewster, clutching the Hunt Cup challenge trophy and flipping through a mental checklist of connections between himself and the Hunt Cup. “It literally was the biggest thrill of my lifetime beyond compare because of the personal and family connections. I really wanted to do it for my family and for those who have gone before and given me the opportunity to do this. I almost feel like it was something I had to do.”

The reasons are many and occupy more than Brewster’s mind. He’s got a list of his family’s connections to the Maryland Hunt Cup. This is only part of it:

• Grandfather and namesake Gerry Leiper Jr. rode the winner (Pebbles) in 1911.

• Grandfather Daniel Brewster rode against Leiper in 1913 aboard Landmark and was third in 1914 with Mullinahone.

• Great-grandfather B.H. Brewster Jr. owned 1919 winner Chuckatuck (who was second in 1917 and 1918) and several other starters.

• Cousin Bill Martin owned 1936 winner Inshore.

• Aunt Polly Denckla owned 1957 and 1958 winner Ned’s Flying.

• Uncle Walter Brewster had several rides, including a third with Cliftons Dan in 1948.

• Uncle Tommy Smith won the race five times. 

• Cousin Duck Martin rode 1972 winner Early Earner.

• Cousin Betty Weymouth owned 1974 winner Burnmac.

• Uncle and godfather Andre Brewster, who died in 2016, owned 1995 and 1997 winner Buck Jakes as part of Arcadia Stable.

What’s more, Gerry Brewster literally grew up at the Hunt Cup. His parents Daniel and Carol Brewster owned Worthington Farms, home to the Hunt Cup since 1922, in the 1950s and 1960s. They sold their portion, south of Tufton Avenue where all but four of the fences are, to relatives Duck and Glennie Martin in the late 1960s. 

“This was my home, and I remember everything about the Hunt Cups in those years that we lived here,” he said. “I grew up here. We lived in that house over there by the barns.”

Brewster’s father was a state delegate and later a United States Representative and Senator for Maryland who co-sponsored the historic Civil Rights Act of 1964. An attorney, his son followed him into politics, also serving in the state House (1991-94) but losing bids for other offices including the U.S. Senate. Brewster’s political career ended in an election loss for U.S. Congress, and he shifted gears to become a public school teacher. He spent two years at Chesapeake High in Essex and five at Towson, where he taught Stierhoff and a young swimmer named Michael Phelps (who did not try to become a jump jockey).

All along, Brewster kept up an interest in the Hunt Cup but he dove back in for real in 2013. Brands Hatch and Catch the Echo carried Brewster’s orange and black silks that year and again in 2014 (neither finished). In 2015, Spencer Road finished third, Catch the Echo was fifth and Brands Hatch lost his jockey. Last year, Derwins Prospector lost his jockey at the first fence, Catch the Echo at the 18th. 

“Going into today, I was the biggest loser in the history of the Maryland Hunt Cup,” he said. “Others have done it more times, but they’ve won. I had never won and 16 times is a record for someone to own a horse and never win the Maryland Hunt Cup. I looked it up.”

Though it’s someone else’s title now, take Brewster’s word for it. He watched the 2017 race unfold in disbelief as the first six fences claimed six horses and Derwins Prospector hung tough.

“I was honestly just hoping he was going to be OK,” Brewster said. “I never at any point from start to finish thought that we had a chance of winning. At no point did I think we had a chance at winning and that’s based on having tried 16 times. You just never even think about it.”


 A messy, but beautiful, race

The race’s only two finishers were half of just four horses remaining (from 10 starters) after six fences. Senior Senator fell and Great Halo refused at the third. Hampered by a loose Senior Senator, De Chera unseated his rider after landing over the third. Super Saturday refused at the fourth. Terko Service and Joshua G. fell at the sixth, the latter with world-class event rider Jennie Brannigan in her first Hunt Cup ride. Our Town (owned by Brewster) lost his rider at the 10th, leaving Derwins Prospector, Drift Society and Old Timer to navigate the final 2 miles.

“After three jumps there was not a lot left and my horse just kept jumping,” said Cottreau. “I did not think that was a big field, that was quite a good field for the race course but I thought there were going to be more to finish and that was a bit of a change when we were the only three left. I just let my horse be confident and enjoy himself, just let him choose his pace. He was happy to jump with them.”

Cottreau, a regular on the FEGENTRI international amateur jockey series and the jumps champion in 2016 and 2015, credited his horse’s jumping ability even while knocking himself a bit for some minor mistakes. At several fences, Cottreau took one hand off the reins as his horse touched down – for balance, a little more margin of error, some flexibility if something went wrong.

“I was calling the taxi a few times, that’s no good but my horse saved me,” he said with a laugh. “That’s me maybe not being confident enough in him. I should have been more confident in his jumping. You come closer to [the fences] and jump pretty high compared to Europe where you stand back more and don’t jump that height so I was a little bit unbalanced sometimes.”

A maiden in nine starts over timber (and 1-for-13 on the flat), Derwins Prospector wound up setting most of a modest pace, with Drift Society for company and Old Timer a few lengths back in third. There have been faster foxhunts through the Worthington Valley, but then a race developed over the final mile.

Derwins Prospector led over the 16th and 17th, but Old Timer outjumped his rivals at the 18th and the 19th. He flew the latter and took a quick, 3-length lead turning toward the 20th. Derwins Prospector was faster there and regained the advantage crossing Tufton Avenue. Third in last year’s race, Drift Society followed on the inside as Old Timer drifted out.

The trio reached the 21st on even terms. Drift Society and Derwins Prospector stayed to the inside and jumped the tricky, leaning board fence (with a small brook on the landing side) together. Old Timer stayed wide, which can help set up a straight line to the 22nd and the stretch, jinked to his right just at the takeoff point and lost McLane Hendriks. Down to two, the race was tight to the last. Drift Society gained a slim lead leaving the second-last, but Cottreau shook up Derwins Prospector for one more push. He accelerated into the last and left with more urgency. Drift Society (Hadden Frost) answered the challenge at first, but Derwins Prospector stuck his head in front in mid-stretch and never yielded another inch.


“Hadden was next to me and we were fighting upsides together,” Cottreau said. “I got the advantage a bit for the last one and my horse met the last fence on stride and it was a brilliant jump. He just kept going and we went for the finish. Thanks to my horse. He was very brave.”

Watching from the hillside, Brewster nearly beat Derwins Prospector to the finish line.

“I was running full speed down the hill and I had no idea who won,” he said. “I was so proud of him. I never thought we were going to win. I just wanted him to get home. I would have been pretty darn happy just to see him get around safely. My angle was terrible so I had no idea.”

Brewster asked outrider Cappy Jackson who won. She turned with a smile and said, “Gerry, you did.”

And the biggest loser was a winner.

“Nobody appreciates it more than Gerry,” said Davies. “It was a meaningful thing for him, you could tell.”

MD Hunt Cup 2017-2-86_RK.jpg

The Road to the Hunt Cup

Horses take a variety of paths to Maryland Hunt Cup glory, with the only common theme involving possession of enough stamina, smarts and jumping ability to become a timber horse. They can be imports (winners have been born in England, Ireland, Argentina, Chile, New Zealand…). They can be homebreds who never set hoof outside Maryland (Moun­tain Dew). They can frequently be rejects from the flat world (Jay Trump is the most well known, but he’s got company). 

Derwins Prospector fits in there somewhere.

Bred in Kentucky by Patricia Lagden and Devi Hall, the son of Van Nistelrooy sold at Keeneland November for $14,000 as a weanling in 2008. His purchaser, Rich Meyer, unknowingly set the Hunt Cup wheels in motion. Meyer, for a time the president of the Maryland Thoroughbred Horsemen’s Association, sent the chestnut to trainer Tim Keefe, and Derwins Prospector finished fourth in his debut as a 2-year-old in October 2010. 

Sold privately by November, Derwins Prospector was at Penn National with trainer Linda Clement, then Hugh Poe and finally Charles “Snake” Frock. The horse’s only flat win came for Frock at Charles Town in July 2011, for a $6,500 claiming price at 37-1. He didn’t win again until the Hunt Cup almost six years later.

Derwins Prospector made nine starts on the flat in 2011, the last a 10th for $4,500 at Laurel Park in November. The next year, the future Hunt Cup winner was running in point-to-points for owner/trainer Lilli Kurtinecz. He failed to threaten in two runs over hurdles, but was second over timber in September and caught the eye of Davies and his wife Blythe.

Davies talked to Kurtinecz and went to see the horse, then training at Mike Hankin’s farm. In one of those twists that seem to flow through the Hunt Cup results, Hankin is a partner in Drift Society.

“He was a little on the weedy side,” Davies said of his first impression. “But he reminded me of [2000 and 2003 Hunt Cup winner] Swayo. He wasn’t as robust, but he had a great jump about him.”

Davies called a client, who agreed to buy the horse. Davies wrote a check and brought the horse home, only to be told something like ‘you know, I don’t think we’re going to do it now.’ Enter Brewster.

The trainer sent an email in October 2012.

“We really like this fellow and think he is a very cool Hunt Cup prospect. His first start as a 4-year-old was a couple of weeks ago at Blue Ridge [point-to-point] where he was beaten a head…”

Brewster, who may have stopped reading at Hunt Cup prospect, sent a check for $10,000 and was in the game. 

“He’d been turned down by several people along the way,” said Davies, “and up until Hunt Cup Saturday at 4:10, everybody looked like they had made the right decision.”

In 2013, Derwins Prospector was a regular on the timber circuit and in the foxhunting field. He got close here and there, but never looked like a real player in the division. His 2014 was pretty much the same, a little progress but no signs of greatness though Brewster did diversify by trading Stifel a half-interest in Derwins Prospector for a half-interest in her horse Pured It.

Last year, Derwins Prospector teamed up with jockey Erika Taylor. They were third at Cheshire Point-to-Point and jumped around the Grand National course, but parted company at the first fence of the Hunt Cup – a result Davies blamed on himself. 

Under professional Gus Dahl, Derwins Prospector finished second at Potomac Point-to-Point last May, but a show-jumping clinic with Olympic silver medalist Greg Best also helped make a difference.

“Greg Best really liked him and said, ‘That is a nice horse,’ ” Davies said. “Then he ran well last fall [second and third in two maiden timber tries] and just made you think we were making some progress.”

Davies’ assistant Ashton Williams rode Derwins Prospector with the Elkridge-Harford Hounds all winter, and also rode him in two point-to-point starts early in the year.

“I always thought he felt like a Hunt Cup horse schooling and hunting and everything,” Davies said. “He’s got great scope, he can jump. He’s just not particularly fast. He should be good at something like the Hunt Cup. He just didn’t get a chance to realize it last year the way things unfolded.”

This year unfolded differently, thanks to Cottreau, better prep races and the various calamities affecting others in the race.

Unlike his more brilliant stablemate Senior Senator, who won the 2016 Hunt Cup and got himself featured on 60 Minutes this spring, Derwins Prospector is a relative saint around the Davies’ Monkton, Md., farm. He’s easy to ride, easy to work around and puts up with plenty – though jumping in and out of turnout paddocks is something of a specialty.

 MD Hunt Cup 2017-2-111_RK.jpg

 “He does jump out of the field, but that’s not an unusual thing here,” said Davies a week after the win. “The day after the Hunt Cup he jumped out of our big open field in front, and he jumped a metal gate in front of [daughter] Scarlett and her friends one day. If we tried harder our horses wouldn’t jump out as much and if it makes them happy it’s a good thing. We’re way back off the road, they never go anywhere.”





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