2023 Kentucky Derby: Best Exacta Box, Picks & Predictions

The 2023 Kentucky Derby is fast approaching, and this year’s run for the roses will have a tough act to follow. In last year’s race (a race I attended), Rich Strike won the race as an 80/1 long shot and entered the race as an alternate after Ethereal Road was scratched from the race.

No, I didn’t have a single dollar on Rich Strike, but I do have a commemorative shirt from the event that doesn’t even have Rich Strike’s name listed!

It can only get better from here, right? Hopefully. But the Derby’s 20-horse field makes this race extremely tricky to handicap, as there are so many variables that can come into play. In this piece, I’ll break down my exotic bets for Saturday’s race.

2023 Kentucky Derby Betting Guide >>

What are exotic bets in horse racing? 

Exotic wagers are like horse racing’s version of parlays in sports betting. They are low-probability wagers that can carry some massive payouts if lady luck is on your side. And like a parlay, you need each leg to occur to win.

There are tons of different types of exotic wagers out there, but for the purpose of this article, we’ll stick to the main three:

  • Exacta: Picking the horses that will come in first and second place.
  • Trifecta: Picking the horses that will come in first, second and third place.
  • Superfecta: Picking the horses that will come in first, second, third and fourth place.

Another unique option in horse racing is the ability to “box” your exotic wagers. When you box a wager, you’re playing all of the possible combinations of your wager. This gives you a better chance to win, but increases your initial wager.

Let’s use an exacta as the simplest example. Say you bet a $1 exacta with Horse A finishing first and Horse B finishing second. If you do a straight exacta, you only win if Horse A and Horse B finish first and second exactly. If you box this exacta, it becomes a $2 wager (because there are two possible outcomes), but you will win if Horse B comes in first and Horse A comes in second.

It’s worth noting that you can bet more than two horses in an exacta, but keep in mind that your wager will increase. Say you take Horse A, B and C in an exacta box, that becomes a $6 wager because of the six possible combinations.

Best Exotic Wagers for the 2023 Kentucky Derby 

$2 Exacta Box: (14) Angel of Empire / (15) Forte

In a race where it’s so hard to pick a single winner, I don’t mind paying a little extra to box up my favorite horses in this race. Angel of Empire intrigues me the most given its four career wins plus its closing ability. I also like the trainer-jockey combo of Brad Cox and Flavien Prat, although both men won their respective Derby via disqualification.

Forte has a great chance of closing as the odds-on favorite, and rightfully so. Forte has six wins in six career races and enters the Derby with the most points during qualifying, including a win in the Florida Derby. Forte has posted triple-digit speed ratings in all six of his outings, but the question will be whether he has the stamina to go the 1 1/4 mile at Churchill Downs.

Both of these horses prefer to run from off the pace, which is my personal preference, as sometimes pace setters can get worn out down the stretch. And closing ability will come in handy in the lengthy Kentucky Derby.


Alternate $2 Exacta Box: (14) Angel of Empire / (6) Kingsbarns

If you’re looking for a juicier, longer shot exacta, I recommend working in the 6 horse Kingsbarns. He’s trained by the renowned Todd Pletcher and is coming off a wire-to-wire victory at the Louisiana Derby, which is one of the closest races in length to the Kentucky Derby. Kingsbarns is one of two horses in this field to win a race at a distance longer than 1 1/8 miles, and that matters at Churchill.


Horses to Consider in your Exotics: 

Finally, here is the full list of horses that I’ll be mixing and matching across my exotic wagers in the Kentucky Derby.

  • Verifying
  • Two Phil’s
  • Kingsbarns
  • Disarm
  • Angel of Empire
  • Forte


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