Kentucky Derby Prop Bets: Margin of Victory A Valuable Play

The most exciting two minutes in sports returns as the Kentucky Derby resumes from Churchill Downs. The 150th annual Run for the Roses gets underway on Saturday, May 4. Betting on the 149th edition of the Derby reached $188.7 million, with all of the first Saturday in May's races betting hitting nearly $300 million. This year's event offers a wealth of fun Kentucky Derby picks to get in on the action. 

Let's dive into the Kentucky Derby Prop Bets odds and pick some winners.

Kentucky Derby Prop Bets

Check out the following 2024 Kentucky Derby prop bets, with many more set to become available on race day.

A Kentucky Derby winner leading wire-to-wire happens a lot less often than you'd think. The last Kentucky Derby winner to complete the feat was Authentic in 2020. However, since 1875 only 23 winners have led from the start and finished with a wire-to-wire victory.

Race favorite Fierceness dominated the Grade 1 Florida Derby at Gulfstream Park, putting up a top-tier 110 Beyer Speed Figure in the process. However, trainer Todd Pletcher has won six of the last 10 Florida Derby's, with only Always Dreaming in 2017 managing to repeat the feat and win the Kentucky Derby.

Thankfully, Fierceness sports a Hall-of Fame trainer (Pletcher) and rider (John Velasquez). He won the Breeders Cup Juvenile last year and has been better in his three-year-old season. Crucially, he loves the lead. If you're on Fierceness to win the Kentucky Derby, sprinkling a few dollars on him to lead from start to finish at +400 odds makes sense.

Will the Kentucky Derby Winner Lead Wire to Wire: Yes (+500)

Odds as of May 4

Betting on the margin of victory is tough. There's always a chance that two of the Kentucky Derby favorites, like Sierra Leone and Fierceness find a way to go neck and neck down the stretch.

The largest winning margin in Kentucky Derby history is a four-way tie at eight lengths, set by Old Rosebud in 1914 and equaled by Johnstown in 1939, Whirlaway in 1941 and Assault in 1948. More recently, 50-1 winner Mine That Bird won by 6 3/4 lengths in 2009, while Barbaro defeated Bluegrass Cat by 6 1/2 in 2006. The odds of predicting a large margin of victory don't match the current field.

Flashback from Barbaro winning the 2006 #KyDerby with ease. pic.twitter.com/8cAdcbR34m

— Kentucky Derby (@KentuckyDerby) April 29, 2019

On the flip side, the smallest possible margin of victory, a nose, has occurred nine times. With the last instance being Grindstone's win in 1996. The turn of the century has seen few close finishes, with only Giacomo in 2005 and the disqualified Medina Spirit in 2021 winning by a half-length. More likely than not, the Derby will be decided by less than one length, which has occurred 44 times in the history of the race. I love the value on 1/2 to 3/4 length at +800.

Best Kentucky Derby Winning Margin Bet: 1/2 length to 3/4 length (+800)

The First Quarter Mile is historically a very popular wager. Speed horses have taken control of the Running for the Roses of late. In fact, eight of the last nine winners have been pacesetters or stalked directly behind the race leader.

Over the last two years, the opening quarter-mile times have been soarsing. The 2022 edition set the record with a 21.78 quarter mile. While the 2023 Kentucky Derby was only slightly behind at 22.35. On top of that, six of the last eight races have come in UNDER this prop of 23 seconds. With Fierceness' speed and tendency to set the pace, I love the UNDER here.

Kentucky Derby First Quarter Mile Best Bet: UNDER 22.8 Seconds (-150)

Kentucky Derby Props and Specials

Kentucky Derby prop bets are fun horse racing wagers where you bet on things that aren’t directly related to the result of that specific horse race. Sportsbooks let you wager on who the winning jockey will mention first in his post-race victory speech, or whether it will be a trainer’s first time winning the Kentucky Derby.