William Woodward had a plan for 1930: Gallant Fox would go for the Belmont Stakes and then certainly would make an appearance at Saratoga for the prestigious stakes races there. All of the Fox’s other races would be dependent upon his condition, but those stakes races were definitely on the list no matter what. That Gallant Fox won the Preakness Stakes and then the Kentucky Derby before the Belmont Stakes happened only because he was fit and ready. “It is called winning the triple crown,” Woodward remarks in his memoir on Gallant Fox, an understated assessment of what the Fox had done to that point. After six straight stakes wins, including the Dwyer and the Arlington Classic, Gallant Fox had come to Saratoga to tick two more races off his list, including the Travers Stakes.

For the Fox, the mile and a quarter Travers should be no problem. To that point, he had already run that distance twice, first in the Kentucky Derby and then in the Arlington Classic, both times winning easily. Now, though, this trip had a new wrinkle: a rematch with Whichone, the two-year-old champion of 1929. Bred and owned by Harry Payne Whitney, Whichone had beaten Gallant Fox in the Futurity at Belmont Park the previous year, but that was at seven furlongs. Whitney’s champion then missed the spring stakes races after bruising a heel and grabbing himself in a workout. Finally, though, they met again in the Belmont Stakes. Prognosticators predicted Gallant Fox’s downfall at the fleet feet of Whichone. Instead, the Fox had run his supposed rival off his feet, sealing America’s second Triple Crown in the process. Afterward, the Whitney colt was found to have a blind quarter crack and given a rest until Saratoga. There, the stage was set for an epic confrontation.

Tom Healey dropped Whichone’s name in the box for the Travers after winning three races in a row at the Spa, including the mile-and-a-quarter Miller Stakes. The Fox had arrived in Saratoga following his turn at Arlington Park, where he had won the Classic on July 12^th and then skipped the Arlington Cup in favor of a break before these late summer starts. Owner William Woodward and trainer “Sunny Jim” Fitzsimmons decided to forgo any races in those weeks between the Classic and the Travers, keeping Gallant Fox trim in workouts with relays of stablemates. His previous win over Whichone and everyone else for that matter made him the favorite for the Travers, but Whitney’s colt had his backers. Whether you pulled for the Fox or for his rival, you knew all of the other horses in the race were just running for third place money.

Besides Whichone and Gallant Fox, the Daily Racing Form had three other potential starters in their August 16^th issue: Caruso, Sun Falcon, and Jim Dandy. Sun Falcon, a son of champion handicapper Sun Beau, was cross-entered in an earlier race on the day’s card. Caruso had had a lackluster season to that point, with only one win in the Sysonby Purse, defeating Sun Beau (yes, you read that right, the sire of Sun Falcon). The field’s long shot was Jim Dandy, a colt with ten starts in 1930 and only one third-place finish in all of those races. One of his two wins at age two was in the Grand Union Hotel Stakes at Saratoga, where he seemed to relish a muddy track. He also was cross-entered in the fourth race on August 16^th, but opted to try the Travers rather than going for the one-mile Waterboy Handicap just one race earlier. For his owner Chaffee Earl and trainer John McKee, it was a fortuitous choice.

Jim Dandy had been less consistent than his famed competitors, with only two wins and two other finishes in the money in nineteen starts. However, this colt was by Jim Gaffney, winner of the 1907 Hopeful Stakes and sire of 1923 Preakness Stakes winner Vigil, out of Thunderbird, a Star Shoot mare. In Jim Dandy’s pedigree were an English Triple Crown winner Isinglass and legendary English sire and Epsom Derby winner Bend Or, names that promised much, but the colt had not delivered — yet. So, on Travers day, it was no surprise that hardly anyone was wagering on Jim Dandy, sending his odds soaring to 100-1. If the day’s gamblers had known what lay in store when the day dawned with a heavy rain-soaked racetrack, those odds might have been shorter.

As the rain continued into the morning of August 16^th, Caruso scratched out of the Travers, making it a scant four-horse field. A record crowd of 50,000 jammed into Saratoga, overflowing the grandstand into the infield. Governor Franklin D. Roosevelt and Eleanor Roosevelt were part of the throng, just two of the thousands waiting to see Gallant Fox and Whichone battle. Sun Falcon took up position on the rail in the first post, with Jim Dandy in post two, then Whichone, and Gallant Fox on the outside. Hours of rain had left some paths on the racetrack deeper than others, so each jockey would need to find the right running lane for his mount or risk racing at a disadvantage. At the break, jockey Sonny Workman moved Whichone to the center of the track, a firmer path than over the rail. With Gallant Fox to his outside, that move forced Earl Sande and Gallant Fox to move with him. The Fox had a slight lead with Whichone staying close for the first mile, the two stars dueling on the lead while Jim Dandy and Sun Falcon ran lengths behind them. They stayed that way for the first mile, coming out of that final turn with 50,000 sets of eyes on only two horses and zero notice for the surprise coming up on the rail.

As they turned into the stretch, just two furlongs to go, Whichone carried Gallant Fox wide, leaving the rail wide open for any horse willing to run in the sloppy lane there. No one should have been surprised to see Jim Dandy flying down the stretch in that path, though; this was the same kind of track he had won the Grand Union Hotel Stakes on the year before. And yet the jammed grandstand and crowded infield must have stood agog at the sight of the longest shot on the board glide over the slick surface and pass those two tired champions. By the time Earl Sande realized that the Fox’s lead had been lost, it was too late to send the exhausted colt after the Jim Gaffney colt. As William Woodward observed in his memoir about Gallant Fox, his Triple Crown champion had enough to outduel Whichone, but not enough to do that and catch Jim Dandy. Even the best horse since Man o’ War had his limits.

Jim Dandy crossed the finish line eight lengths in front of Gallant Fox, who straggled home another six lengths ahead of Whichone, with Sun Falcon bringing up the rear. While the battle played out on the track, the mass of people watching, both the famed and the anonymous, watched in stunned silence, astonished by the unexpected. They expected the white with red polka dots or the Eton blue with brown, but this jacket, the blue with white sleeves, was the height of upset. Was that stunned silence followed by gasps when they saw what was next?

With the battle done, Workman pulled Whichone up as soon as they crossed the finish line, H.P. Whitney’s champion clearly suffering. In the process of setting a suicidal pace and doing everything he could to beat Gallant Fox, Whichone bowed a tendon, ending his career. He would never race again.

Gallant Fox came out of the race none the worse for his test. By finishing second, he inched a bit closer to setting a new record for career winnings, but that milestone would wait for a different day. As for the Travers, Woodward acknowledged that “had we been drawn inside of Whichone, I am very confident that the Fox would have won,” for Workman would not have been able to push Gallant Fox wide nor would Sande have felt compelled to engage in that duel. Instead, they looked to his next start in the Saratoga Cup and the chance to get back to the Fox’s winning ways.

As for Jim Dandy, he joined the ranks of horses like Upset as a dethroner, those horses that give Saratoga its nickname of “Graveyard of Champions.” The Travers would be his one win of 1930 and his last victory of consequence. His owner Chaffee Earl eventually would give his Travers winner to trainer John McKee, who kept Jim Dandy in training until 1939. In his career, Jim Dandy would start 141 times, with only seven wins over his many seasons on the track. He had a second career as a dressage and jump horse, a horse loved and well cared for until his death. In 1964, the New York Racing Association immortalized this unlikely Travers winner with a stakes race named for him. At a mile and an eighth, the Jim Dandy Stakes often serves as a prep race for the Travers Stakes, with winners like Street Sense, Bernardini, and Arts and Letters going on to win the Travers as well.

Ninety years ago, in a year where Gallant Fox became America’s second Triple Crown winner and looked to go undefeated at three, he ran into a rival and found himself another victim of the Graveyard of Champions, his infamous Travers defeat a “jim-dandy” of an upset. Will we see another one this year? We shall find out when this year’s Travers Stakes goes off with a field of eight, including the favorite Tiz the Law, on Saturday, August 8th at 6:15 pm Eastern.

For more on the history of the Travers Stakes, including Jim Dandy’s 1930 victory, I recommend picking up The Travers: 150 Years of Saratoga’s Greatest Race by Brien Bouyea and Michael Veitch, a Dr. Tony Ryan Book Award semifinalist. Order the book today!