On January 14, 1932 Eddie Arcaro won his first race as a jockey on a horse named Eagle Bird at the Aqua Caliente Race Track in Tijuana, Mexico.

Arcaro was not yet a licensed jockey, he was only 15 years old.

Once he turned 16 and acquiring a jockey license, Arcaro became employed in New Orleans at the Fair Grounds Racecourse.

Due to his strong work ethic and charisma, Warren Wright of Calumet Farms in Kentucky hired him to ride some of the best thoroughbreds.

In 1941, Arcaro won the Triple Crown on Whirlaway and again in 1948 on Citation.

Arcaro won a grand total of 4,779 races in his career, including the Kentucky Derby five times, the Preakness Stakes six times and the Belmont Stakes six times.