The beloved racehorse Zippy Chippy, famous for losing all 100 races in his career, has passed away at the age of 31.

Since 2010 the gelding had spent his retirement at the Bobby Frankel Division of Old Friends Thoroughbred Farm at Cabin Creek in upstate New York. While there is no official cause of death, a spokesperson from the farm said the bay horse died last Friday, April 15.

Zippy Chippy enjoyed a long and happy retirement. ( photo)

According to the history books, Zippy’s owner, Felix Montserrate, traded a 1988 Ford truck for the horse in 1995. While his breeding indicated that Zippy had winning in his blood – that included Man O’ War, Native Dancer, and Bold Ruler – destiny had other plans.

While Zippy Chippy failed to enter the winner’s circle, he did cross the finish line in second place eight times and placed third 12 times. As fate would have it, he was barred from many tracks due to his penchant for hijinks, including refusing to break from starting gates.

The public loved the stories of the most losing horse in racing and in 2000, Zippy landed on People magazine’s list of the year’s most intriguing personalities.

In August of 2001, Zippy Chippy defeated a minor league baseball player in a 40-yard dash. He also won against a harness horse in which he spotted the trotter a 20-length lead. So speed was in there; just not when it came to actual horseracing.

“Zippy was our main character here and he lived his life his way,” JoAnn Pepper, owner and manager of Cabin Creek, said in a statement. “He was so content, and would not do anything he wasn’t in the mood for. He taught me so much about life, and I’ll miss him forever.”

According to the farm, the sport’s most “loveable loser” attracted hundreds of fans to the farm each year. Said Michael Blowen, Old Friends founder and president, “He was finally a star.”