Mayor Fischer makes annual Derby wager with Ocala Mayor

May 1, 2019

Mayor Greg Fischer and Ocala (Fla.) Mayor Kent Guinn today made their annual wager on the Kentucky Derby, placing a bottle of Woodford Reserve bourbon and Ocala brandy on the line.

This is the sixth year of the friendly wager between the mayors of the two cities, both of which are steeped in thoroughbred tradition and consider themselves spirited rivals for the status of Horse Capital of the World.  

Mayor Fischer this year picked Improbable, breaking from post position 5, to win the 145th Kentucky Derby and make the time-honored walk to the infield Winner’s Circle for the garland of roses. Improbable was bred in Kentucky, is trained by Bob Baffert and will be ridden by Irad Ortiz.

“Improbable is one of the Baffert trio of horses, which is what makes it interesting to me, and is the same owner/trainer combination as last year’s Triple Crown winner. As a bonus, Improbable has won at Churchill Downs, and as we all know, a win at Churchill helps in the Derby,” Mayor Fischer said.

Mayor Guinn chose Win Win Win, breaking from post position 14, because he’s a Florida-bred thoroughbred raised in Ocala at Live Oak Stud. Win Win Win is owned by Ms. Charlotte Weber, trained by Michael Trombetta and will be ridden by Julian Pimentel.

Mayor Guinn noted that it will be an “Ocala Derby,” with the honoring of J.B. McKathan, an iconic member of the Florida horse racing family and trainer of Triple Crown winner American Pharoah. McKathan tragically passed away Feb. 2, 2019.

Last year, Mayor Fischer’s choice, Mendelssohn, trained by Aidan O’Brien, finished 20th, and Mayor Guinn’s pick, Magnum Moon, finished 19th.

“The road to the Kentucky Derby begins in Ocala, Fla., Horse Capital of the World. This year is no different with 17 of the 20 horses having ties to our city,” Mayor Guinn said. “This annual bet with Mayor Fischer has become a tradition I look forward to, and it’s a fun way for us to unite the equine industry. We hope this will finally be the year that one of our horses is victorious!”

Mayor Fischer bet a bottle of Louisville-based Brown-Forman Corp.’s Woodford Reserve signed by Master Distiller Chris Morris and artist Keith Anderson. Woodford Reservice is the official bourbon of the Kentucky Derby. Mayor Guinn again bet Marion Black 106 — the Spirit of Florida Tangerine Brandy, distilled by Fishhawk Spirits of Ocala.

“We’re looking forward to welcoming Mayor Guinn and his return to Louisville for the Derby,” Mayor Fischer said. “No matter which horse you pick, you always win with a trip to the Derby and experiencing all that Louisville has to offer.”