With five starts behind him, Sir Barton’s shiny pedigree with its English Triple Crown winners and juvenile superstar half-brother was starting to look a bit tarnished. All of the flash and form he showed to clockers in the morning had yet to make an appearance in the afternoon when it truly mattered. John E. Madden sold the colt to his friend J.K.L. Ross with the promise of pedigree and performance, but with 1918 on its way out, Sir Barton needed to make good on those promises.

He had been in the barn of H.G. Bedwell for not quite a month, but the Hard Guy must have seen something starting to unlock in the Star Shoot* colt for they took advantage of Madden’s foresight to nominate the colt in the Belmont Futurity as a foal and entered him for the 1918 edition of the most prestigious juvenile race of that era. Sir Barton had fourteen other competitors on the sandy oval of Belmont that day, including Duboyne and Purchase, two other good juveniles who promised to make waves in 1919 as well. The fifteen went to the barrier at 3.46 pm on Saturday, September 14th, with Sir Barton in the thirteenth post, far on the outside, and a young Earl Sande on his back.

At the break, Sir Barton came out in sixth and then eased in behind the front runners, Duboyne, The Trump, and Pigeon Wing. At the half-mile pole, he was fourth; at the three-quarters, he was third. In the stretch, as Pigeon Wing began to fade, Sir Barton moved up into second, only a length and a half behind Duboyne, who had been on the lead for the whole race. Andy Shuttinger shook up Duboyne and the colt increased his lead to 2 1/2 lengths over Sir Barton at the finish, but, as J.K.M Ross writes in Boots and Saddles, Commander Ross “seemed more pleased with the result than I had ever seen him. […] Even on the following day, while lunching with Duboyne’s owner at the old Ritz-Carlton, my father was still smiling so broadly that anyone would have thought it was his horse and Mr. Clark’s that had won” (132).

Sir Barton’s first finish in the money portended even more when Earl Sande recounted his experience at the start of the Futurity. Had Sir Barton not been boxed in by the general tangle of a large field, he likely would have had a chance to move into a position that would have allowed him to catch and even pass Duboyne.

In October 1918, before Sir Barton could get another start in at two, a kick from another horse opened a cut on his stifle, which soon became infected. The resulting blood poisoning sent the colt’s temperature to a dangerous 105 degrees, but Bedwell, who had lived intimately with horses since he was a young man, nursed Sir Barton until he recovered. The illness put the son of Star Shoot* on the shelf for the rest of 1918, not to be seen again until Derby Day 1919.