A century ago, Jan. 21 saw racing in the midst of its yearly changing of the guard, the champions of 1920 giving way to their successors.

With a new year came new discussions, new names, and new possibilities to consider for those celebrated events that populate our calendar. The business of racing went on – at Havana, Fair Grounds, Tijuana – but the race we will celebrate one hundred days from now in 2021 was still more than one hundred days off in 1921.

Of course, that expanse of time was no deterrent to promises of the greatest Kentucky Derby yet, as Col. Matt Winn boasted. The eyes of racing world had turned toward that dash for roses contested under twin spires, the Kentucky Derby, even as it said goodbye to its most immortal name.

New Shooters

The previous year’s 2-year-olds were now three, eligible for more chances for greatness in classics like the Derby. The horses that had dominated 1920’s juvenile races were in the mix for the season to come, but one stood out above the rest: Inchcape. A son of Belmont Stakes winner Friar Rock, Inchcape was the colt that had dominated his two starts, winning both so easily that comparisons to Man o’ War had already begun. His potential led famed trainer Sam Hildreth to purchase the colt for $150,000, an extraordinary sum in this era.

On Jan. 21, 1921, oil magnate Harry Sinclair then purchased Inchcape for his Rancocas Stable, picking up where famed owner Pierre Lorillard had left off in the late 19th century. Immediately, Sinclair nominated Inchcape for the 1921 Kentucky Derby, fully intending to send his dominant colt to Louisville.

As Inchcape dominated the news, the champion colts and fillies of the previous year had yet to start in 1921, but all were part of those Derby conversations. Harry Payne Whitney’s Prudery had beaten both colts and fillies at two, winning the Grand Union Hotel and the Spinaway before finishing second in the rich Hopeful Stakes.

Whitney also had Tryster, undefeated in his six races in 1920, including the inaugural Kentucky Jockey Club Stakes. Walter J. Salmon’s filly Careful shared best juvenile filly of the year honors with Prudery, winning 12 of her 17 starts.

Alongside Inchcape, Harry Sinclair had another of 1920’s good juveniles, Grey Lag, as a Derby hopeful. Grey Lag was one of the last foals of Star Shoot, sire of Triple Crown winner Sir Barton, and his performances in races like the Champagne and Remsen made him a leading candidate for the Derby on May 7.

Farewell to a Legend

While the 3-year-old division had plenty of horses to watch, racing fans were not quite done with one particular name: Man o’ War.

Arguably the greatest horse to ever look through a bridle, “Big Red” was about to say farewell to the racetrack for good, his owner Samuel Riddle content that his champion had achieved all that he could in his two seasons.

The Kentucky Association track in Lexington, Keeneland’s predecessor, was preparing for the grand occasion where Man o’ War was going to parade in the paddock under colors for the last time before departing to Hinata Farm for his stud duty.

On Jan. 21, as Col. Winn touted the 1921 Kentucky Derby as the greatest yet, he did so in the shadow of the immortal who had never raced in the state of Kentucky, but ironically would spend the rest of his days there, the name Man o’ War forever evoked as the greatest to never seek or wear roses.

A century ago on January 21…

A century ago, on Jan. 21, as they looked forward to another Derby, to the emergence of another name to add to the list of victors of America’s greatest race, racing fans might have gone to the opening of Charlie Chaplin’s latest film The Kid, and, before the feature, watched The Race of the Age, the exclusive film of the match race between Sir Barton and Man o’ War, that immortal’s final race. As they watch those two greats streak across the big screen, did they talk of the next horse that could challenge Big Red for their hearts? Did they debate the merits of Grey Lag and Tryster, of Prudery and Careful? As they watched two of racing’s greats and considered champions of the past, did they count down the days to roses as we do?