Foaled in Kentucky, he was out of the mare Golden Dust and was sired by Sportin' Life, who in turn was the son of the British Triple Crown champion Nijinsky.
Bet Twice was owned by a syndicate of approximately three dozen that included baseball players Pete Rose and Garry Maddox.
Early in his three-year-old season, Bet Twice won the grade two Fountain of Youth Stakes on the road to the Triple Crown.
He met a crop of talented horses in that three-year-old year, including Gulch and Cryptoclearance; however, his rivalry with Kentucky Derby and Preakness Stakes winner Alysheba was most famous.
Ridden by Craig Perret and trained by Jimmy Croll, he won by 14 lengths and denied Alysheba the Triple Crown.
When Bet Twice was four, his connections accepted an invitation to run him in the first revival of the $500,000 Grade I Pimlico Special Handicap at "Old Hilltop" in Baltimore, Maryland.
He entered that race as the post-time fourth choice at odds of 7–1 in a field of seven graded stakes winners, including Crytoclearance.