How to Bet $100 at the 2026 Kentucky Derby

LOUISVILLE, Ky. — Todd Pletcher, trainer of Kentucky Derby favorite Renegade, was on a plane to Louisville when he learned his colt drew the dreaded No. 1 starting post.

“I reached for the air sickness bag,” Pletcher said, a good line for one of the more serious trainers in the sport.

Drawing the No. 1 hole in the Derby might not be the stroke of doom it was before Churchill Downs went to a single, 20-horse gate, creating a little more room to maneuver into the first straightaway. But still: It’s the easiest place to find traffic trouble, and the last horse to win the race from that post was Ferdinand 40 years ago.

Thus, I’m tossing the favorite from my $100 betting plan. What looked like a wide-open race before the post-position draw is even more uncertain now.

With that in mind, feel free to take your wagers wherever you have conviction. This could well be a “Who’s That?” Derby, where the winner is charging down the stretch and people are feverishly scanning their programs to see which obscure long shot is about to render their wagers useless.

The four horses I’m working with are: Chief Wallabee (8–1 in the morning line), Commandment (6–1), Further Ado (6–1) and Emerging Market (15–1).

The horses I’m worried will nuke my plans: Japanese import Danon Bourbon (20–1), Santa Anita Derby winner So Happy (15–1), The Puma (10–1) and, yes, Renegade (4–1), if he can overcome the post position.

But that’s why it’s gambling—you cannot cover every eventuality. There is no shortage of guesswork involved.

I’m expecting the usual stout early pace that should burn up the front-runners when they come off the turn and head for home in the 1 1/4-mile race. That group should include Litmus Test (50–1), Six Speed (50–1), Pavlovian (30–1) and Robusta (50–1). At that point, the race will belong to the smartly positioned stalkers and the strong closers. Here’s the play:

I’m starting my $100 investment with a $20 win bet on Chief Wallabee. This is a moderate leap of faith on trainer Bill Mott, who won this race last year with Sovereignty and also captured the 2019 Derby by disqualification with Country House. Like Sovereignty, Chief Wallabee is coming to Louisville off a non-victory in the Florida Derby (Sovereignty was second, Chief Wallabee was third in a blanket finish). I am expecting the Chief to make a similar jump forward Saturday to what Sovereignty showed. The same jockey is aboard as well in Junior Alvarado.

I’ll play a three-horse, $5 exacta box with Chief Wallabee, the Brad Cox–trained Commandment (who won the Florida Derby by a nose) and another Cox trainee, Further Ado (who blew away a soft field in the Blue Grass Stakes). A “box” means that if any combination of those three finishes 1–2, it’s a win. That’s a $30 wager.

Then it’s time to try the trifecta. For the sake of simplicity here, let’s make it a four-horse, $2 box with Chief Wallabee, Commandment, Further Ado and Emerging Market. That’s a $48 bet.

The final $2 is for the Rich Strike saver bet. After watching that animal somehow win the 2022 Derby at 81–1 odds, it’s worth saving a couple dollars to place on the longest shot on the board. Stranger things can and have happened.

Go to the windows and bet with confidence. Just don’t blame me when it doesn’t work.

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