Four, five, six times on the walk to the paddock for the Maryland Hunt Cup Saturday, race favorite Senior Senator ran into the back of stablemate Derwins Prospector. The latter, a longshot with nothing but defeats in nine starts over timber, put up with the punishment like a tolerant older dog adapting to life with a new puppy in the house.

Except once.

About halfway through the walk, which traverses part of the course and takes 16 minutes, Senior Senator got especially close and Derwins Prospector took offense. With a hump in his back, he bucked and stutter-stepped away before going back to his job of taking lumps from the punk.

And then the role model got his revenge.

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. Owned by Gerry Brewster and trained by Joe Davies, the winner outfinished Drift Society by three-quarters of a length in 9:46.20. French amateur Gonzague Cottreau rode Derwins Prospector, who quadrupled his career earnings with the $60,000 payday.  

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 event rider Jennie Brannigan in her first Hunt Cup ride. Our Town 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 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.”

Not for long. 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. 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 a bit.

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 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.”

The Hunt Cup win was the latest paragraph in a long, meandering racing story for Derwins Prospector. Bred in Kentucky by Patricia Lagden and Devi Hall, the son of Van Nistelrooy sold at Keeneland November as a weanling in 2008. Owner Rich Meyer sent the chestnut to Tim Keefe in Maryland, and Derwins Prospector finished fourth in his debut as a 2-year-old in October 2010. By November, he was at Penn National with trainer Linda Clement, then Hugh Poe and finally Charles “Snake” Frock. Derwins Prospector’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 five years later.

Derwins Prospector made nine starts on the flat in 2011, the last a 10th for $4,500 at Laurel Park in November. By 2012, 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 was sold to Brewster. By 2013, Derwins Prospector was a regular on the timber circuit and in the foxhunting field. He got close here and there (placing in some point-to-points and finishing second at Genesee last fall), but never looked like a real player in the division. In 2016, he lost his jockey Erika Taylor at the first fence of the Hunt Cup.

This spring, Derwins Prospector teamed up with Davies assistant Ashton Williams and finished second at Piedmont Point-to-Point and a fourth at Elkridge-Harford. Cottreau flew in to ride the 9-year-old in the Grand National April 22 and Derwins Prospector finished fifth behind Senior Senator. Now, it looks like an encouraging run. Then, it was just another race.

“Well, that wasn’t what we expected,” said Davies wife and chief assistant Blythe on the walk toward the winner’s celebration. She spoke for many.

Cottreau, who heard all about the Maryland Hunt Cup from Senior Senator’s jockey Eric Poretz last year, may have been new to the historic race but winning owner Brewster goes way back.

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

• Grandfather Daniel Brewster, rode against Leiper in 1913.

• Great-grandfather B.H. Brewster Jr. owned 1919 winner Chuckatuck.

• Gerry Brewster grew up on Worthington Farms, home to the Hunt Cup since 1922 (his family sold their part of the property to Duck and Glennie Martin in 1969.

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

• Uncle and godfather Andre Brewster, who died in 2016, owned 1995 and 1997 winner Buck Jakes.

• Gerry Brewster rode in the race four times, finishing second in 1986.

Counting 2017, he had competed in the race as an owner 16 times without winning. He calls himself “the biggest loser of the Maryland Hunt Cup.” Others have sent horses to the post more often, but not without winning at least once.

“There’s a lot of history here,” said Brewster, who co-owns the horse with Adair Bonsal Stifel. “To come home after trying 16 times and win is an amazing feeling. Phenomenal. It literally was the biggest thrill of my lifetime beyond compare because of the personal and family connections. I am so happy for all the people who worked so hard to make this happen – Ashton Williams, Joe and Blythe Davies obviously. They are unique talents in timber racing.”

The Davies have now won six Hunt Cups combined. Joe three times as a jockey and twice as a trainer. Blythe once as a jockey.

Brewster watched the race from the hillside and ran the final yards with Derwins Prospector and Drift Society.

“I was running full speed down the hill and I had no idea who won,” he said. “At no point did I think we had a chance at winning and that’s based on having tried 16 times. You just sort of, you never even think about it.”

Until now.

NOTES: The Hunt Cup was sloppy, but horses and riders escaped without major injuries . . . The original field of 11 was reduced by one when Serene Harbor was scratched at the start . . . Two finishers is not all that out of the ordinary as it happened in 2009 (Michele Marieschi over Rosbrian), 2006 (Bug River oer Rosbrian), 1996 (Hello Hal over Florida Law), 1981 (Cancottage over Blaze Miller) and three consecutive years from 1967-69 . . . The 1915 race included 23 starters and just eight finishers, and two of those were remounted after falling.