Bold Venture, trained by
Hall of Fame conditioner
Max Hirsch, was entered in the 1936
Kentucky Derby without achieving a single
stakes win. His rider was
apprentice jockey Ira "Babe" Hanford, who had been riding in races for less than a year. Hanford's contract was owned by Hirsch's daughter, Mary, also a trainer. Just as Hanford's mount had never won a stakes race, no apprentice had ever won the Derby. Bold Venture was held at 20-1 odds in the Derby. That year, Brevity, owned by
Joseph E. Widener of
Elmendorf Farm, was the favorite. Brevity had won the
Florida Derby and had equaled the world record for 1 1/8 miles.
Indian Broom, owned by
Austin C. Taylor, was second favorite after lowering Brevity's record in the
Marchbank Handicap. As soon as the gates opened, Brevity was knocked to his knees, and the horse who would go on to win that year's American Horse of the Year award,
Granville, threw his rider,
James Stout. Indian Broom was trapped in a scrum of racing horses. Bold Venture was in no better position. On the way out of the gate, another horse slammed into him, which was like, Hanford said: "...a bowling ball hitting the pins." This started a chain reaction that caused Granville to throw Stout. But Bold Venture then found running room and by the
backstretch had taken the lead. Then Brevity broke free of the pack and came charging after Bold Venture. However, Bold Venture crossed the finish line first. The win did little for Bold Venture's reputation. Aside from the mess at the start,
Charles Kurtsinger, the rider of the
Santa Anita Derby winner He Did, claimed someone leaned over the rail and snatched his whip, causing his horse to come in seventh. Two weeks later, Bold Venture was entered in the $50,000
Preakness Stakes. This time ridden by
George Woolf, he had a second bad start but still won, beating Granville by a nose. Undefeated in his three-year-old season, and with two legs of the
Triple Crown won, Bold Venture
bowed a tendon and was retired. ==Stud record and death==