Flipcup, pride of the Penney family, retires; will be bred to Speightstown

Wednesday, May 2nd, 2018

(L to R) Shirl, Ann Clare, Mary Ann and Townsend Penney lead Flipcup to the winner’s circle (TDN photo)

By Sarah Mace

When Shirl Penney recently decided to retire multiple graded stakes winner and fan favorite Flipcup, the decision was bittersweet. Penney bred Flipcup, attended her foaling and campaigned her into her sixth season under the banner of “Team Penney Racing.” Above all, he regards the mare as family.

“Some horses are extra special to us as owners and breeders – the ones you truly fall in love with and count as part of your family,” said Penney. “Flipcup was one of those horses for the Penney family.  From being there when she was foaled, to her racing career in many states over many surfaces, and now onto her next career as part of our broodmare band, she is for us what this sport is all about to us: fun with family and friends, and about building special bonds with our horses.”

Penney, his wife Mary Ann and their daughters Ann Clare and Townsend have been along every step of the way of this accomplished racemare’s career. They will miss the excitement of campaigning Flipcup but also look forward eagerly to the next chapter.

Sired by Milwaukee Brew, Flipcup is out of Dream Affair, a Kentucky-bred Touch Gold mare purchased by Penney for just $11,000 at the 2007 OBS Winter mixed sale. Foaled on March 29, 2011, Flipcup was prepared for her racing career by Kenny Lejune in Florida (who also broke Penney’s Grade 2 stakes winner Sweet Vendetta) and burst onto the racing scene as a juvenile. Her first stop was Woodbine.

Flipcup won right out of the box for trainer Brian Lynch taking a pair of sprints run over the all-weather track. (September 14, 2013 and October 11). Stretching out for the first time in Woodbine’s South Ocean Stakes on November 24, Flipcup finished a competitive third to eventual three-time Sovereign Award winner Lexie Lou and top Canadian filly Paladin Bay. Flipcup traveled to New York for her final juvenile start, when she made her New York and dirt debut for trainer George Weaver. That day, Flipcup won Aqueduct’s East View Stakes going away. Flipcup’s achievements as a juvenile earned her a nomination for New York-bred champion 2-year-old juvenile filly.

Flipcup’s her first campaign was a blueprint of sorts for each racing season to follow.

G3 Maple Leaf Stakes at Woodbine 10/31/2015 (Michael Burns photo)

As a daughter of Milwaukee Brew, and therefore eligible for stakes restricted to Canadian-sired horses, Flipcup returned to Woodbine at least once every year through 2017. Her connections weren’t shy either about taking her even further afield. By retirement Flipcup had raced at nine different racetracks, where she competed successfully on dirt, synthetic and turf.

Flipcup also went on to win at least one stakes race in each of the next four years and each of those years her success was rewarded with a nomination for a New York-bred divisional championship (champion 3-year-old filly in 2014 and older dirt female in 2015 and 2016).

When Adam Wachtel partnered with the Penneys on Flipcup for her sophomore campaign in 2014, she moved to the barn of Bill Mott. Adam also brought his frequent partner Nils Brous in on the partnership.  Penney said, “Adam Wachtel is 25-percent partner now and will remain so into her next career.  He is a fantastic partner!  We also enjoyed having Nils as a partner during her racing career and am happy she won stakes races in all three of our silks over the years.”

At three Flipcup won New York Oaks at Finger Lakes, earned five more stakes placings in New York-bred restricted stakes and at Woodbine and took home nearly $200,000 in earnings. At four, Flipcup joined the ranks of graded stakes winners, taking the Grade 3 Maple Leaf at Woodbine where she also won the Classy ’n Smart Stakes. The following year Flipcup picked up more graded black type when she shipped to Arlington Park and won the Grade 3 Arlington Matron.

Arlington Matron 5/28/2016 (Four Footed Fotos)

By the time she hung up her tack, Flipcup had started 36 times, won five stakes races, led by her two graded victories, and earned 14 additional stakes placings. The final tally of her earnings bankroll is $691,732.

“Bill [Mott] and his team did a great job with her,” said Penney, “as did Brian Lynch in Canada and George Weaver before the move to Mott when Adam bought in.”

The Penney daughters bid bon voyage to Flipcup before she boards a KY-bound van to be bred to Speightstown

Flipcup retires sound but experienced a minor issue after her last race on April 2 (an $80,000 allowance/optional claiming race at 1 1/16 miles on turf at Aqueduct), which led to the decision to stop on what would have been her sixth and final campaign.

Explained Penney, “We retired her after her last race as her ankle was a little sore and we talked to Bill Mott and just decided we could still breed her this year. We decided to stop on her as would never risk anything with her. Her entire career she has been sound – never one issue ever, amazingly. We planned to campaign her this year as her last. While she has been second in stakes on grass we wanted that [turf stakes] win to make her very rare mare having won stakes on all three surfaces.”

Penney settled on WinStar stallion Speightstown to be the sire of Flipcup’s first foal. “Speightstown is A++ nick to her and has been as consistent a sire as any in country last few years. We do business with Winstar and think very highly of them and are excited to send her to their farm.” For the pregnancy and foaling Penney is thinking of bringing Flipcup back to Jerry Bilinski’s Waldorf Farm in North Chatham where she and Sweet Vendetta were foaled.

Reflecting on Flipcup’s racing legacy and place in the family, Penney said, “She was a fun ride winning stakes at two, three, four and five and being full of heart and ran nearly every time she set foot on track. Mary Ann and I and our daughters visited her daily at Mott’s barn [from our house on the Oklahoma training track] and will miss her. She is 19 times stakes-placed on all surfaces, a four-time New-York bred divisional championship nominee, and a very fun and loving horse to be around.

Then Penney mused, “Maybe someday we’ll have a New-York bred race called ‘The Flipcup’, I hope so!” It is not farfetched to think that if there is a Flipcup Stakes, one of her offspring could win it.

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