Photo-Match: Definitive photo-matches have been made to the following races: 1996 Massachusetts Handicap (Alamy 2PFEKBW) and 1996 Arlington Citation Challenge (Getty 235088). Photos have been uploaded in the listing.
Presented here is what may be the most comprehensive Jerry Bailey racing "uniform" ever offered at auction. Most importantly, Lelands has photo-matched the silks offered here to those worn by Bailey during the 1995 and 1996 racing seasons, which is the reason we are attributing the uniform to those two years. It was during those two racing seasons that Bailey was the exclusive jockey for Cigar, the two-time Horse of the Year (1995-1996) and winner of sixteen straight races, including the 1996 Breeder's Cup Classic. Jerry Bailey won 5,893 races during his illustrious career, including two wins each in the Kentucky Derby, Belmont Stakes, and Preakness. When he retired in 2006, he ranked second on the career North American money list with $296 million (currently ranks third). He was elected to the United States Racing Hall of Fame in 1995.
1) Silks: The colorful red-white-and-blue silks show excessive wear from being worn in multiple races, with conclusive photo-matching to multiple races. Here is a list of total style matches: 1995 Breeder's Cup (Getty 51992230) and 1995 Jockey Club Gold Stakes (Getty 456863842), 1996 Dubai World Cup (Getty 229210), 1996 Massachusetts Handicap (Getty 456863866), 1996 Arlington Citation Challenge (Getty 72281225). Including numerous areas of pilling, wear to logo on front, and a few holes on the left sleeve. There are numerous pinholes on the right shoulder strap, where he pinned his number badge. "A. Paulson" (for Allen Paulson, Cigar's owner) is embroidered in red on the interior left front tail. A "Fast Colors" label appears on the left front tail. Handwriting in red marker on the interior left-front tail reads "Bree, $3,000 Cup, BOS" (possibly indicating Bailey's 1995 Breeder's Cup $3,000,000 win at Belmont). The number "833" and the crossed out numbers "394" and "698," along with an illegible name (not Bailey) appear in black marker on the rear interior tail.
2) Boots: Each of the black boots, with red trim, shows excessive wear. This same style of boot can be seen worn by Bailey throughout 1995-96 racing seasons. Each has Bailey's initials, "J.D.B.," written on the interior in black marker.
3) Helmet with hat: "Caliente" safety helmet by McHal, together with a blue silk riding hat. The helmet, with white chin strap, is well worn, with numerous exterior nicks and abrasions, and an application of several strips of tape. The blue silk cap that covers the helmet has "Bailey" embroidered in white on the reverse. EX.
4) Goggles: Pair of clear riding goggles. Bailey has signed the googles twice, once on either side in black marker (grading 6/10). The goggles display heavy wear.
5) Pants: Pair of white riding paints. "Bailey" is embroidered in blue stitch on the reverse exterior waistband. The pants display excellent wear.
6) Undershirt: White short sleeve undershirt. "J.D Bailey" is lettered on the front in black lettering, directly below which is an image of horse and rider. The shirt shows displays heavy wear, including sweat stains on neck
7) Socks: Pair of brown socks. Each has "J.D Bailey" printed in black marker and these can be seen in numerous photos we found.