Our Top Sportsbooks

2021 Kentucky Derby Predictions and Best Bets

Kentucky Derby Betting Odds

The 147th running of the Kentucky Derby (G1) is here, run just eight months after a delayed 2020 Run for the Roses due to the pandemic.

A full field of 20 will line up, there will be a limited number of fans under the Twin Spires at Churchill Downs, and it will be a blockbuster day of wagering action with 14 races on tap with first post of 10:30 a.m. ET.

It is time for a few Kentucky Derby predictions, and we have to talk about the favorite Essential Quality first. The undefeated colt is the 2-1 morning line favorite and is currently listed at +275 in early Kentucky Derby wagering at Bovada.

The colt seemed likely to go off at 3-1 or 7-2 but Jim “Mattress Mack” McIngvale of Gallery Furniture announced his plans on wagering between $2 million and $4 million on the Derby favorite. Mack is running a mattress promotion for his customers: Spend $3,000 or more on a mattress and get a full refund if the betting favorite wins the Kentucky Derby.

To offset the cost, McIngvale said he would wire Churchill Downs $4 million and place some or all of the money on the favorite, which is certainly going to be Essential Quality. In 2019, $41.8 million was wagered in the Win pool in the Derby, meaning Mack’s bet is going to move the needle and make Essential Quality an underlay in the race.

The colt is not flashy but can be close to the pace or sit off if the pace is sharp. He had to work a bit harder than I thought he would last out in the Blue Grass (G2) at Keeneland but did earn a career top speed figure. However, with Mattress Mack dropping a $2-million to $4-million win bet on this guy, getting 3-1 or 7-2 is out the window.

He checks all the boxes, a solid two-year-old campaign capped off by his win in the Breeders’ Cup Juvenile (G1), and he broke his maiden in his debut over the main track at Churchill Downs. The main knock is 2-1 or 5-2 is just an underlay.

If you’ve never previously bet on the Kentucky Derby or horse racing and are unsure of which sportsbook to use, don’t sweat it. Odds Shark has put together a handy Kentucky Derby Betting Guide that even seasoned bettors may want to review to ensure you’re picking the best betting site for you

Who Are the Live Long Shots in This Year’s Derby?

Medina Spirit +1400

Medina Spirit at +1400 in the latest Derby wagering odds at Bovada gets the call as a live long shot as his trainer, Hall of Famer Bob Baffert, goes for a record seventh win in this race. The colt is coming off a solid second in the Santa Anita Derby (G1) that produced the only triple-digit Beyer Speed Figure among the Derby preps, belonging to the winner Rock Your World, who earned a 100 while taking the field gate to wire while down toward the inside on the best part of the racing surface that day.

The colt actually broke on top and it looked as if he might be sent to the lead, but the winner got in front with a long shot in between them running a little interference going into the first turn. The Baffert trainee chased the winner and weakened in the stretch to finish 4¼ lengths behind the winner at 4-5. Medina Spirit has four starts under his belt this year and earned a 99 Beyer for his runner-up finish in the Sham (G3) to kick off the year, and then won the Robert B. Lewis (G3).

He was no match for his stablemate Life Is Good in the San Felipe (G2), beaten eight lengths by the then favorite for the Derby. It is tough to take the field gate to wire but Baffert did it last year with Authentic. With a clean break, this guy may be able to get to the lead and that may be the strategy. If not, he will be sitting in a good position just off the pace. I doubt this colt goes off at 15-1 with Baffert calling the shots but still should end up offering decent value.

Highly Motivated  +1200

Highly Motivated gave Derby favorite Essential Quality all he could handle last out in the Blue Grass (G2). He set the early fractions and led until deep stretch when the champ finally got to him nearing the wire to win by a neck. The colt did not switch leads smoothly but earned a career top speed figure and finally got over his tendency to break a beat slow.

His last was his first trip around two turns. He had a rough trip two back in the Gotham going a one-turn mile. He was off a step slow when bobbling, had to steady nearly hitting the temporary rail and then was caught in tight heading down the backstretch, came with a four-wide bid and finished up well for third, beaten 1¾ lengths. The top pair came back to run third and fourth in a slow edition of the Wood (G2).

The colt seems to be getting better with each start and while trainer Chad Brown is 0-for-5 with his Derby starters, Good Magic ran a solid second and Normandy Invasion ran well in a fourth-place finish. This colt looks as if he has some upside and is quick enough to get a good position and hopefully stay out of trouble. He is by Into Mischief out of the stakes winner Strong Incentive ($123,568), who won a restricted stake at a mile on turf at Woodbine. He does not have the strongest pedigree in the field to get the distance, but he is tactical, has good connections and should end up a fair price.

Other Contenders

Rock Your World (+475) is going to end up the second choice and that won’t get the pulse racing. His Santa Anita Derby win was solid but may have been aided by the racing surface. It was his first start on dirt, his first two career outings coming on turf. He is bred to run all day, by Candy Ride out of the stakes winner Charm the Maker (Empire Maker). He reunites with Joel Rosario for trainer John Sadler, who is 0-for-4 with Derby starters. If Medina Spirit is sent, that is going to hurt this guy’s chances.

Hot Rod Charlie (+800) won the Louisiana Derby (G2) and I liked the race and I think Mandaloun is going to bounce back. But that 42-day break bothers me. The winner was bumped coming out of the gate, pressed the early pace and drew clear late to win by two lengths.

Mandaloun (+2200) was the beaten favorite in the Louisiana Derby, tracking the early pace, looking as if he was going to make a move and then just ran out of gas, fading to finish nearly a dozen lengths back. The colt has been working sharply since and seems likely to bounce back with a much better effort for the Cox barn.

Kentucky Derby Best Bets

The main question is how to wager on this year’s Kentucky Derby?


Medina Spirit is worth a win wager if we get odds of 8-1 or better. The same goes for Highly Motivated if we see odds of 6-1 or better.


It is going to be Medina Spirit and Highly Motivated in the top spot using Essential Quality, Rock Your World and Hot Rod Charlie for minor awards. If you are playing trifectas and superfectas, I would also recommend using Known Agenda, Mandaloun and Dynamic One in the third and fourth spots.

When is the Kentucky Derby?

This year’s Run for the Roses will be contested Saturday at 6:57 p.m. ET at Churchill Downs. The race is the 12th of 14 on the card. Horseplayers can catch the action from 12:30 p.m. to 2:30 p.m. on NBCSN, and then from 2:30 p.m. to 7:30 p.m. on NBC.