George Smith, The 1916 Derby and Beyond
By Eliza McGraw

The Outrider by Eliza McGraw

One hundred years ago, a horse named George Smith won the Kentucky Derby. His name seems like it could say a lot about the horse. Humble, plain, straightforward. But like his name—and his namesake, actually–George Smith was not what he seemed on paper. And in his complexity, he represented the world of racing at the time, which included sagacious gamblers, beautiful horses, and the constant cycling of figures that would play a role in the Man o’ War story.

The original George Smith, the horse’s namesake, was better known as Pittsburg Phil. (The horse got the name was because Phil had owned the horse’s dam.) He was a systemic handicapper who wrote a book of maxims that included things like, “A man cannot divide his attention at the track between horses and women,” and “a horse that is not contented in his stable cannot take on flesh and be happy.” He watched horses carefully, so he could tell what condition they were racing in. He once made $290,000 in three days, which, as Kevin Martin points out, would equal over $7 million. Phil died in 1905. “He was known as the bookmaker’s enemy,” read one of his obituaries, in the Los Angeles Herald in 1905.

George Smith the horse seemed to have internalized some of Phil’s maxims. Phil would have studied George Smith’s appearance: he was a handsome black colt, with what a New York Times reporter called, “wonderful conformation and silky coat that indicated the acme of fitness for the struggle.” He had just one race before the Derby, said his trainer, Hollie Hughes. “We shipped early in April from Charleston and raced George Smith late in April at the old Lexington track. This was the only race he had as a 3-year-old before the Derby. It was a mile and a sixteenth. A nice mare named Bayberry Candle beat him, but he was giving her 21 pounds on the scale.”

George Smith was a strong Derby contender; his owner John Sanford didn’t usually start his horses in Kentucky. But because he had George Smith, he did. The actual race was not particularly fast—2 minutes, 4 seconds. Harry Payne Whitney’s colts Dominant and Thunderer—who had never beaten, and was the brother of Regret, the previous year’s winner–were the favorites. George Smith was the third in the betting—he went off at 4-1.

Johnny Loftus was in George Smith’s saddle for the 1916 Kentucky Derby. Loftus would go on to ride Sir Barton to his Triple Crown victory, the first in history– the term wasn’t used yet—making him the first Triple Crown jockey. He would also ride Man o’ War during his two-year-old season in 1919, when the colt took the racing world by storm. But on Derby Day 100 years ago, Loftus had never won a classic race.

Derby Day was beautiful in 1916, warm, with only clouds of the “rainless, friendly sort,” as Thomas B. Cromwell wrote in the Daily Racing Form. The crowd was one of the largest that had even been to a Derby, 30,000 including the infield. But the most exciting thing in the Kentucky Derby seemed to be the performance of a horse named Star Hawk. He was English, and evidently struggling to understand American starts. So he was almost left behind, reported the Washington Post. “He did not seem to strike his stride until half of the race had been run, when he came with a terrific rush overtaking the field one by one, except the winner.” George Smith’s performance was enough to win the race by a neck, but apparently it was not as astonishing to onlookers as Star Hawk’s rush. In fact, the DRF’s Cromwell believed that had Star Hawk had Loftus aboard, he would have won, not George Smith. Still, Kentucky governor A. O. Stanley gave George Smith the roses, and gave Loftus a bouquet, too.

If his actual Derby had not been particularly remarkable, though, George Smith had the opportunity years later to make up for it with a dazzling performance in a unique Bowie Handicap, which was run at Pimlico in November of 1918. He ran against two other Derby winners, Exterminator and Omar Khayyam. It was “the greatest field of handicap Thoroughbreds ever sent to the post in Maryland,” wrote Edward Sparrow in the Baltimore Sun. The New York Times agreed that it the field included “the best horses in training.” Besides the Derby winners, other strong contenders were Corn Tassel, who would go on to win the Suburban in 1919; Cudgel, who vanquished Exterminator and Sir Barton in 1919; The Porter; and War Cloud. Jockey Frank Robinson rode George Smith.

George Smith showed resilience and talent in that race. He had to deal with interference at the beginning, but once Robinson moved him up on the outside, he had a “great burst of speed.” The two other Derby winners caught up, and the three headed for the finish, but George Smith maintained his lead to win, setting a new track record of 2:31 1/5 for the mile and a half.

George Smith’s victory was honestly earned,” Harry N. Price wrote in the Washington Post. “At the finish the son of Out of Reach was doing his best, and Frankie Robinson was riding the best he knew how to stall off the bold challenge of Omar Khayyam and the rush of Exterminator.”

“It will go down in the history of Pimlico as one of the greatest contests ever run at the Maryland Jockey Club’s course,” wrote Price.

George Smith may have been a lackluster Derby winner a hundred years ago. But he raced into history like his namesake, Pittsburg Phil.

ProQuest Historical Newspapers database
“George Smith Runs Away From Rivals,” New York Times, September 29, 1918, 28
“Kentucky Derby to George Smith,” The Washington Post, May 14, 1916, 53
Price, Harry N. “George Smith Sets New Track Record,” Washington Post, November 13, 1918, 10
Sparrow, Edward. “The Bowie Attractive,” Baltimore Sun, November 12, 1918, 15
And thanks to Kevin Martin for his work on Pittsburg Phil on Colin’s Ghost.

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