1913, Donerail
1913-1915: The Kentucky Derby Makes Front Page News
For three consecutive years—1913, 1914 and 1915—the Kentucky Derby hit the front page news and was finally established as a premiere American sporting event. Here's what happened...
First, in 1913, Donerail, the underdog in the 38th running of the Kentucky Derby race, upset the field, with 91-1 odds. Donerail still stands as the biggest long-shot victory, paying $184.90 on just a $2 win bet.
Second, in 1914, Old Rosebud won the Kentucky Derby with the fastest recorded time in its 40 year history, just over 2 minutes and three seconds. Old Rosebud won the race 8 lengths ahead of the second place finisher, setting another record, for the longest distance between the 1st and 2nd place finishers, which would take another sixteen years to break.
1914, Old Rosebud
Historical Archive
Third, in 1915, a filly named Regret raced in the Kentucky Derby, and was the first female Thoroughbred to win. Regret is one of only three fillies who have ever won the Kentucky Derby.