Zippy Chippy on Tour in Central Kentucky

Racing's losingest horse is on loan from Old Friends' New York division.

Zippy Chippy, racing's losingest horse, will spend the summer at the Old Friends Thoroughbred retirement center in Georgetown, Ky. He is on loan from the organization's satellite facility in Greenfield Center, N.Y.

The now 21-year-old gelding, best known for losing 100 consecutive races, is part of an Old Friends exchange that sent two-time Whitney Handicap (gr. I)  winner Commentator to Old Friends at Cabin Creek, Bobby Frankel Division, and brought Zippy to Kentucky. Commentator will be at Cabin Creek through the Saratoga meet visiting with all of his fans.

Zippy Chippy arrived in Georgetown July 13 along with his buddy Red Down South courtesy of Sallee Vans. Both horses will stay at the Georgetown facility through August.

"This must be the worst trade since the Red Sox sent Babe Ruth to the Yankees," joked Old Friends founder and president Michael Blowen. "Actually, Zippy, whose motto is 'winners don't always finish first,' has a huge fan base here in Kentucky, and we're all looking forward to having him with us in Georgetown."

Owned and trained by Felix Monserrate, Zippy Chippy made headlines in the 1990s for his failure to make it to the winner's circle in over 80 starts. In 2000, People magazine included him on its list of the year's "Most Interesting Personalities." The gelding's continued losing streak and his ornery nature resulted in his being banned from most racetracks by the late '90s, but he continued to run at the Three County Fair in Northampton, Mass. On April 10, 2004, Zippy made his 100th start. Finishing dead last, it was to be his final trip around the oval. The gelding retired to Cabin Creek in 2010.

Commentator raced six seasons for owners Tracy and Carol Farmer and Hall of Fame trainer Nick Zito. He ended his career in 2009 having won 14 of 24 starts and a bankroll of $2,049,845. Besides his two Whitney victories, the son of Distorted Humor  won the $500,000 Massachusetts Handicap by 14 lengths. He was retired to Old Friends in Georgetown in October of 2009.