1983: two-year-old season

Conditioned for racing by future U.S. Racing Hall of Fame inductee Woody Stephens, Devil's Bag was ridden by Eddie Maple. The colt won all five starts at age two by an average of five and a half lengths and was voted the American Champion Two-Year-Old Colt of 1983. His wins included the seven-furlong Cowdin Stakes in a stakes record time of 1:21.40 at Belmont Park. He set another stakes record at Belmont Park in winning the one-mile Champagne Stakes by six lengths, breaking Seattle Slew's 1976 record time. In his final race as a two-year-old, Devil's Bag won the 1¹/16 mile Laurel Futurity Stakes by five and a quarter lengths in a time of 1:42.20 that broke the track record set by Spectacular Bid. Scheduled to run in December's Remsen Stakes at Aqueduct Racetrack, while in training the colt stepped on a stone. Although the injury was very minor, his handlers chose not to race him again that year.

On December 20, 1983, it was announced that a syndicate led by Seth Hancock's Claiborne Farm paid $36 million for Devil's Bag, the highest price for any 2-year-old in racing history, and the third highest for any race horse ever. Hancock said that the colt would be retired to stud at Claiborne Farm after his three-year-old racing season with his 1985 fee set at $1 million for his first stallion year.^[3]

1984: three-year-old season

Devil's Bag was the winterbook favorite for the U.S. Triple Crown series. Such was his fame that a January 2, 1984, Time magazine article led with: "Devil's Bag, the next Secretariat."^[4]

Devil's Bag made his three-year-old debut on February 20, 1984, at Hialeah Park Race Track, scoring a seven-length win. However, on March 7 he suffered the first loss of his career in the 1⅛ mile Flamingo Stakes at Hialeah Park. After taking the lead heading for home, Devil's Bag suddenly slowed down and finished fourth. A March 12 article in Sports Illustrated called it "one of the most stunning surprises in recent racing history, for no 3-year-old since Secretariat, in 1973, had stirred the imagination more than Devil's Bag."

On April 19, Devil's Bag returned with a fifteen-length victory in the seven-furlong Forerunner Stakes at Keeneland Race Course and then won his next start on April 28 at Churchill Downs in the one-mile Derby Trial Stakes. He was the pre-race favorite for the May 5 Kentucky Derby. Then, on May 1, trainer Woody Stephens announced that Devil's Bag would not run in the Derby but that he might start in the Preakness Stakes.

On May 7, it was announced that veterinarian Dr. Alex Harthill had discovered a small fracture in Devil's Bag's right front knee and that the colt would be retired from racing.