James “Jimbo” Bailey is retiring after an impressive 56-year career as a jockey valet at Finger Lakes Gaming & Racetrack, where he became a beloved figure in the horse racing community. Starting as a hot walker and groom, Bailey worked closely with legendary jockeys like Bill Shoemaker, Jerry Bailey, John Velazquez, and most notably John Davila Jr., whose record of over 4,000 wins at Finger Lakes remains unmatched. Beyond the races, Bailey cherished the deep friendships and family-like bonds formed at the track, which kept him dedicated to the sport for more than five decades.

As Bailey steps away from the racetrack, he looks forward to enjoying retirement with his wife, planning road trips, visits to national parks, and sunny days in Florida. Though leaving the job he called a blessing is bittersweet, his impact and presence will remain a lasting part of the Finger Lakes racing family. Colleagues and riders alike recognize Bailey not only for his professionalism but for the warmth and camaraderie he brought to the jockey room throughout his remarkable career.