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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, clutch- ing the Hunt Cup challenge trophy and flipping through a mental checklist of con- nections 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
secondin1917and1918)andseveralother starters.
• Cousin Bill Martin owned 1936 win- ner 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 win- ner 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 liter- ally grew up at the Hunt Cup. His par- ents 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,torelativesDuckandGlennieMartin 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-spon- sored 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 politi- cal 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
Former Hunt Cup winner and current board member Liz McKnight (left) presents the trophies to a happy bunch including co-owners Gerry Brewster (white hat lifting Hunt Cup challenge trophy) and Adair Bonsal Stifel (brown hat lifting the Hunt Cup tankard) plus trainer Joe Davies (third from left) and jockey Gonzague Cottreau. Hunt Cup veterans Walter Brewster (second from left) and Frank Bonsal (far right) join the celebration. Opposite: Still battling after nearly 4 miles, Derwins Prospector (left) and Drift Society jump the last fence on even terms.
18 Mid-Atlantic Thoroughbred JUNE 2017

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