Kentucky Derby 2023 betting strategy: Horses to bet on and expert tips

The Kentucky Derby is the single greatest wagering opportunity in all of sports.

Granted, that does not roll off the tongue as effortlessly as the most exciting two minutes in sports, but it is just as true.

Last year, there was $179-million bet on the Kentucky Derby. With the track retaining about 20%, that means bettors competed for a share of about $143.2 million. That is the money we are trying to win. So, how do we do it?

The good news is part of our competition is all the bettors betting Mage because their uncle is a magician, or Raise Cain because they’re an Hebrew scriptures scholar or specific numbers because it’s their address/anniversary/birthday/social security number.

All those are fine ways to enjoy betting the Kentucky Derby, but there is no finer way than with a big score, and here’s how I think I’ll do it this year.

First, the general game plan is to identify the horses I like best (Tapit Trice and Skinner) and least (Confidence Game, Continuar, Derma Sotogake, Jace’s Road, Mage, Kingsbarns, Raise Cain and Reincarnate). With rare exception, I will need one of the horses I like best to finish in the trifecta while none of the ones I like least can.

With two horses in the “boss” pile and eight in the “toss” pile that leaves 10 others still in the mix. I further split those 10 into win contenders (Forte, Practical Move and Two Phil’s) and exotics contenders (Angel of Empire, Disarm, Lord Miles, Hit Show, Rocket Can, Sun Thunder and Verifying).

My wagering strategy for 2023 Kentucky Derby

Take the two horses in the boss column and play them in exactas with the other 10. That costs $18 with one of the boss’s winning and another $18 to use them in second underneath the other 10 ($36 total).

Take Skinner, who will be a big price, and play him in exactas with the other boss (Tapit Trice) plus the win contenders from the secondary list. That’s $4 each way for $8 total.

Take the two boss horses in a trifecta with the win contenders and then the secondary list. So one of the two bosses has to finish first, one of the five win contenders has to finish second, and one of the 12 from the non-toss list has to be third. That costs $40. I’d then make the same bet with the two bosses in second behind the win contenders for another $40. That’s $80 in trifectas.

Total bet: $124, and if it comes Skinner, Two Phil’s, Disarm then we’ll win thousands. Watch this space after the draw for additional discussion, including program numbers and how to call various bets.