2024 Kentucky Derby Betting: Which Longshot Can Upset Fierceness, Sierra Leone?

Written By Eli Hershkovich | Published at May 2, 2024

The opening horn is nearing for Kentucky Derby odds. TheLines caught up with veteran horse-racing handicapper Mike Wilkening to find out his strategy for the 150th Run for the Roses. Below, you will find his Kentucky Derby picks, including an intriguing longshot bet to fend off morning-line favorites Fierceness and Sierra Leone.

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Kentucky Derby picks: pace expectation

Although many variables are in play for the greatest two minutes in sports, one certainty is the Derby's mile-and-a-quarter distance of the race is no sprint. If a contestant puts too much onus on the early goings, he likely won't participate in the purse distribution at the end.

But could there be a pace meltdown in store? This term refers to two or more front-running horses fighting for an early lead, wearing one another out. Ultimately, these instances benefit horses who took it easy early on and have enough energy for a late surge. It occurred as recently as 2022, with 80-1 longshot Rich Strike crossing the finish line after there was a pace meltdown in which they flew through early fractions of 21.78, 45.36, and 1:10.34.

Wilkening cites the 2013 Derby as another bona fide pace meltdown. This time, the contenders galloped from behind, accentuating the rapid pace. Ultimately, Orb, entering the race as the 7-2 betting favorite, emerged victorious by two-and-a-half lengths, followed by 50-1 longshot Golden Soul and 10-1 Revolutionary. Nevertheless, Wilkening anticipates a healthy pace this coming Saturday, but that doesn't insinuate that morning-line favorite Fierceness is immune to adversity.

"Some pay close attention to the final three-quarter mark, but it's really that final half mile, where horses separate themselves," Wilkening said. "I don't think it's going to be a case where the speed horses spit the bit, but the chaotic part could be if Fierceness doesn't run 'his race.' There have been a couple of races where he's been done around the turn. If that happens, you can probably pick the winner out of a hat."

Which Horse Syncs Up?

Speaking of pace, Mystik Dan's closing speed caught Wilkening's eye at Southwest Stakes (G3) on Feb. 3. Fellow Derby candidate Just Steel, the son of Triple Crown winner Justify, rushed to the lead at the quarter pole from post No. 4 under jockey Ramon Vasquez.

However, Mystik Dan skipped past him on a muddy inside stretch. Conditions could be eerily similar at Churchill Downs. While he isn't necessarily bred to go the full mile and a quarter, he's shown the ability to stride out well in the waning moments.

"He'll probably fall into a trip where he's in fourth, fifth, or sixth (early on)," Wilkening said. "He's got his jockey, Brian Hernandez Jr., who's one of the foremost (riders) at saving ground and isn't afraid to come up the rail. That's not a terrible place to be. When horses decelerate off the turn, they often leave the inside open.

"He (Mystik Dan) might get a trip similar to what Two Phils (who finished second) got last year."

Wilkening is targeting Mystik Dan, concerning straight bets and exotics, at 20-1 odds. He expects Mystik Dan to still sport an attractive price for bettors waiting until Derby day to place their wagers. If Fierceness avoids the upset, Wilkening thinks the three-year-old colt will accomplish the same feat in the Preakness. He's priced at 9-2 in the latest futures pool.