By early November, 1919 had become a year of mixed blessings for jockey Johnny Loftus. He had been aboard Man o’ War for all of his victories — and his lone defeat. Loftus had ridden winners for a number of racing’s top stables and trainers, everyone from Sam Hildreth to H.G. Bedwell. He had won a Kentucky Derby on Sir Barton but also lost the Dwyer Stakes to Purchase, who Loftus also had ridden to victory that year. Loftus had been set down for rough riding, yet he also had served as trainer Louis Feustel’s go-to rider for a fractious and challenging Man o’ War. With the year winding down, Loftus was looking forward to 1920, possibly his final year in the saddle. Years of fighting his weight left the jockey ready to consider what’s next. In the meantime, he was ready to finish out 1919 on a high note.

The Autumn Handicap on November 5th would prove to be anything but.

Sir Barton came into the race as the heavyweight, laden with 132 pounds. Sailor was the lightweight at 96, with Mad Hatter, a horse on a hot streak, carrying 111 pounds despite his recent wins. Pimlico had absorbed heavy rain the night before, but winds had started to dry the surface, leaving the track cuppy, especially at the rail. Sir Barton had proven himself to be more than capable of handling an off track, but the Dwyer demonstrated that the colt had trouble running on the rail on a drying track. Loftus had ridden Sir Barton in the Dwyer so he should have been familiar with the colt’s difficulty in handling that type of track. But the jockey had no other mounts that day, opening up the possibility that he was not aware of how the surface was playing.

Bridesman took the lead at the start, with Sir Barton’s stablemate Milkmaid challenging. Mad Hatter stalked the pace just behind the two leaders, Sir Barton running behind him. As they hit the six-furlong mark, Mad Hatter made his move out in the center of the track as Loftus asked Sir Barton for more down on the rail. Mad Hatter passed Bridesman, Fator looking for Sir Barton to press for the lead as well. Instead, Loftus and his mount labored behind Bridesman, the heavy impost and cuppy track slowing Sir Barton’s move. When it was clear that they would not catch Mad Hatter, Loftus eased Sir Barton, who finished twelve lengths back of the winner. It was a dull performance from a horse who had been asked to carry 132 pounds after a long campaign. But to finish third by twelve lengths to a horse he had already beaten? Trainer H.G. Bedwell was livid.

What happened next opened up a schism that rocked the Ross Stable and may have changed one man’s life for good. Read more in Chapter 10 of Sir Barton and the Making of the Triple Crown.