(This blog post is the second in a series of four, profiling the first horse to traverse what we now know as the Triple Crown trail. In 1918, one horse started in the Kentucky Derby, the Preakness Stakes, and the Belmont Stakes for the first time, inspiring Sir Barton’s run in all three the following year. You can read part one here.)

In 1916, A.K. Macomber sent his imported colt, Star Hawk, to the Kentucky Derby as one of the historic race’s favorites. Not quite a year into his reentry in American racing, Macomber was poised to win his first Kentucky Derby, tantalizingly close to one of those dream moments all horse owners seek. Instead, jockey Johnny Loftus on a colt named George Smith held off the driving Star Hawk in the stretch to win the Derby for owner John Sanford. Coming that close to winning the Kentucky Derby prompted Macomber to search his growing stable for another chance at the roses. He tapped War Cloud to carry the red and white Macomber stripes in the 1918 Kentucky Derby.

Early on, his likely competition seemed to be the champion two-year-old colt, Sun Briar, owned by Willis Sharpe Kilmer. A bad beat in a prep race and the poor workouts that followed prompted Kilmer to keep the juvenile champion out of the race. That left Escoba, owned by native son Kenneth Alexander, and War Cloud as the race’s probable favorites. War Cloud had been shipped to Louisville more than a week before the Derby and his workouts since he had arrived had given many observers cause to believe that War Cloud was the best horse. Trainer Walter Jennings sent the colt the Derby route of a mile and a quarter the Monday before the race and, carrying 127 pounds, ten more than he would carry on race day, War Cloud ran 2:05 2/5. Macomber’s colt seemed to be building on his two-year-old form, a season where he won four of his six starts. On race day, War Cloud went to the post as the favorite, with jockey Johnny Loftus on his back.

After Star Hawk lost the 1916 Derby to George Smith, Macomber sought out Johnny Loftus’s services, making him the stable’s star jockey. Two years later, Loftus served as War Cloud’s regular rider, both for morning workouts and afternoon races. With a family to support, Loftus was eager to score another Derby win, this time for Macomber, his millionaire boss. With his star jockey on his back, War Cloud strode onto the Churchill Downs dirt track, ready to face the barrier again. What he found under his feet was the difference between dominance and defeat.

Days of rain left the dirt pocked with puddles, a surface antithetical to the long stride of a horse like War Cloud. Speed would find no purchase here; this was the kind of track that favored horses who didn’t need a fast track to run their best race. As the field strode to the post, War Cloud was followed in the post parade by a Kilmer-owned horse, but it was not Sun Briar. Exterminator had been purchased for $9,000 by Kilmer’s trainer Henry McDaniel, who needed a workmate for Sun Briar. Instead, when Sun Briar wasn’t ready for the Derby, Colonel Matt Winn, the promoter who had made the Kentucky Derby into an event, convinced Kilmer to send Exterminator. War Cloud took his place in post four, the long and homely Exterminator stood next to him, in post five. It was time to run.

At the break, the filly Viva America took the lead, Escoba and Sewell Combs on her heels. Six furlongs into the race, the filly gave way to Escoba and then Exterminator, as those two moved into the lead. As the two battled for the lead down the stretch, Escoba did his best to stay with Exterminator, but gave way in that last eighth of a mile. Exterminator, the gelding who had been an afterthought for his owner, won the Kentucky Derby at odds of 30-1, paying $61.20 for the lucky few that had put their money down on the unknown horse. The 1918 Kentucky Derby started the gelding on a path that would make him a legend in his sport.

Meanwhile, the favored War Cloud, Macomber’s hope for the Derby, never factored in the rain-soaked race. The muddy going made it difficult for the colt to find his footing while interference from other horses left him unable to run in a more ideal position. His roadblocks left him struggling home at race’s end, finishing four lengths behind Viva America, who had hung on for third. War Cloud barely had time to wash off his Derby mud before he was loaded onto a railcar, racing toward Baltimore for another prestigious race, the Preakness Stakes.

Only eight horses had gone to the barrier for the Derby, with a half-dozen good horses opting to stay back in Maryland rather than ride the rails to Louisville. A shortage of available railcars might explain some of that, but truly there were fifteen thousand other reasons to be in Baltimore. The Maryland Jockey Club had announced it would add $15,000 to the purse for the Preakness Stakes, matching the money added for the Kentucky Derby and making it a hot target for the 144 horses nominated for that race. On that list and a train bound for Baltimore was War Cloud, another step closer to making history.