2023 Kentucky Derby picks: Betting strategy for big race

Whether you play the ponies regularly or just throw a couple of bucks on the Triple Crown races, it’s still a fun challenge to come up with a handicapping strategy for a race like the Kentucky Derby.

With 19 of the best 3-year-old horses in the world competing, the “Run for the Roses” always has potential for chaos and this year is no different.

Though people betting favorites will want the race to stay predictable and go as planned, those who make bets hoping for bedlam can get paid off quite handsomely.

There have been plenty of four and five-figure trifecta payouts in this race over the years and almost all of them have the same thing in common: Things went batty.

So here are a couple of chaos narratives to work with in order to build a ticket that has high upside: 

Fade the common narrative

One thing you’re going to hear a lot about from the railbirds in your life is that this iteration of the Kentucky Derby lacks early pace and that the best horses (Forte, Tapit Trice and Angel of Empire) are all closers that will make late charges and pick up the pieces down the stretch.

It’s quite possible that the race plays out like that and the three favorites get the race they’re hoping for, but what if things fall apart a little bit and one of the horses that enjoys getting out to an early lead is able to put too much distance between himself and the closers?

Even if you like betting the favorites, you should, at the very least, have a ticket or two that sets yourself up for that scenario.

Playing a long shot like No. 7 Reincarnate (16/1 down from a morning line of 50/1) could provide a nice payoff if he is able to get out to, and maintain, a lead long enough to hit the board. 

Buy low on the No. 1 position

It’s really hard to win the Kentucky Derby out of the No. 1 position.

There are 19 horses all trying to get themselves into position and if you’re being squeezed from the outside by 18 of them, you’re in for a rough go.

But this is not some secret.

Everybody knows that the No. 1 horse is going to have a tough time, which means very few people will bet him.

That market sentiment usually leads to a pretty significant discount. 

Kentucky Derby 2023 Betting: Everything you need

Hit Show (36/1) is the unlucky No. 1 this year, but there are a lot of people who are pretty bullish on his chances to perform better than his current odds, which likely will be higher by the time the race goes off.

The last horse to win from the No. 1 spot was Ferdinand back in 1986, so if we see something historic and you get it right, you’ll get paid off handsomely. 

The $1 Superfecta

In terms of upside, there are few bets in all of sports that have better “lottery-ticket potential” than playing a $1 superfecta (getting the first-, second-, third- and fourth-place horses right) at the Kentucky Derby.

Since 2005, there have been 13 payouts of at least $10,000 and four that hit six figures, including last year.

So pick a couple of long shots, toss them into a superfecta box and pray.