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How to Bet the Kentucky Derby: Finding the Best Value for a Bigger Pay Day

If you like Essential Quality as your bet to win the Kentucky Derby, I’m sorry. The prospective payout is small and likely to get smaller.

The unbeaten two-year-old champion was established as the 2–1 favorite in the morning line by Churchill Downs oddsmaker Mike Battaglia, lower than many expected. “I thought he might be 3–1,” said Essential Quality trainer Brad Cox, “but I’m not betting, so. …”

“Mattress Mack” is betting, and his promised wager will further diminish the price on Essential Quality if the gray colt wins the Run for the Roses. Jim McIngvale, owner of the national Gallery Furniture chain, told me he wired $4 million to Churchill on Wednesday in preparation for betting on the Derby favorite in a promotion tied to his chain’s mattress sales. “I may bet $2 million, I may bet $4 million,” he said, aiming for a total that would cover his guarantee to reimburse every Gallery Furniture customer who buys a mattress worth $3,000 or more if the favorite wins.


Mattress Mack’s monster bet could be the largest single wager in the 147-year history of the Derby, seemingly certain to hammer Essential Quality’s odds down closer to even money. The only horse sent off at shorter than even money in the last 28 runnings of the Derby was last year, when Tiz the Law was the 7–10 favorite at post time. He was repulsed in a vigorous stretch duel with Authentic.

Does Mattress Mack know what he’s doing? From a business perspective, this is a smart play. From a handicapping standpoint, not necessarily. McIngvale attended his first Derby in 1971 and has been in the thoroughbred ownership game for a long time, but that doesn’t make him a racetrack sharpie.

“Generally, I don’t pick too well,” he said. “I couldn’t pick my brother out of a roomful of giraffes.”

Those of us betting less than $2-4 million also will be trying to avoid picking a giraffe to win. It’s never easy figuring out how to bet a 20-horse race, since the permutations are endless. By week’s end, the information overload is real—everyone has a different theory, and everyone has different insight into how the horses look in the morning workouts.

But it all boils down to an essential question about Essential Quality: Is he as far ahead of his peers as the morning line suggests?

With a 5–0 record and virtually no complications along the way, he’s a deserving favorite. Looking for holes in his game to this point is fairly futile. But should be really be sent off at, say, 4–5?

That kind of price is an invitation to find value elsewhere, and the two most enticing candidates are Hot Rod Charlie at 8–1 and Rock Your World at 5–1.


Hot Rod Charlie burst onto the scene with a strong second-place finish to Essential Quality last November in the Breeders Cup Juvenile at odds of 94–1. He then punched his Derby ticket with a win in the Louisiana Derby in March. In both cases, the son of 2013 Preakness winner Oxbow was on or near a solid early pace and did not falter late.

Hot Rod Charlie has trained sharply at Churchill this week for Doug O’Neill, who has won this race twice. At odds of 8–1, he’s arguably the best value among the top contenders.

Rock Your World (5–1 morning line) presents both a higher upside than Hot Rod Charlie but also greater risk. He did not race at two years old, which from 1883 until 2017 was an impenetrable impediment to winning the Derby. Then Justify did it in 2018, on his way to the Triple Crown, breaking the so-called Curse of Apollo (last unrated two-year-old to win the Derby to do it before Justify, in 1882).

Like Justify, Rock Your World comes from California unbeaten in just three races. Like Justify, he was dazzling in winning the Santa Anita Derby—perhaps signifying the arrival of a real monster. Unlike Justify, he is not trained by Bob Baffert, who has won six Kentucky Derbies and knows better than any man alive how to get it done on the first Saturday in May. Rock Your World trainer John Sadler is a well-regarded West Coast conditioner, but his four previous Derby entrants have never finished better than sixth.

The third betting choice in the race is 6–1 Known Agenda, the Florida Derby winner trained by Todd Pletcher. The horse drew the rail in the No. 1 spot in the starting gate, generally considered the kiss of death in this 20-horse brawl for position heading into the first turn. That may not be a reason to totally toss Known Agenda from your wagering plans, but proceed with caution.

At 10–1, Highly Motivated was beaten by just a neck by Essential Quality in the Blue Grass Stakes, giving the unbeaten champ his toughest test so far. If he can replicate that effort here, he should be in the mix in the home stretch.

Among longer shots, the intrigue lies with a trio of horses that were beaten by Hot Rod Charlie in the Louisiana Derby: Mandaloun (15–1) threw in a mysterious clunker there after going off as the favorite but has impressed on the Churchill track; Midnight Bourbon (20–1) was second in Louisiana but picks up jockey Mike Smith for the Derby, a race in which he’s won twice and finished second four times; and O Besos (20–1), who showed an intriguing late surge and may benefit from the additional distance of the Derby.

The race could be contested from posts 14–17 in the starting gate. Essential Quality breaks from 14, Rock Your World from 15 and Highly Motivated from 17. How they break and then position themselves—and how the pace unfolds—could be the decisive factors.


On paper, this doesn’t look like a group that will burn through the first half of the 1 1/4-mile race. If it’s a softer pace, that could set up well for horses who figure to be on the front end, like Hot Rod Charlie and Rock Your World, and could add pressure to Essential Quality jockey Luis Saez not to let them get away.

Ultimately, I see Hot Rod Charlie and Rock Your World with the lead heading into the stretch and Essentially Quality trying to close in the final furlong. I’ll bet that Essential Quality gets to the wire first in a thrilling finish.

So I’ll make a modest win bet on him at flattened odds, plus boxing an exacta with those three horses, and I’ll factor in the rest of the Louisiana Derby pack plus Highly Motivated in the trifecta and a small swing at the superfecta. I’m no Mattress Mack, though. The total bet will be in the neighborhood of $100, with the full expectation that some horse I haven’t considered all week will hit the board and blow it all up.

Good luck to all who make a wager.

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