How One Massachusetts Horse Bettor Did With His Kentucky Derby Wagers

Written By Jack Flaherty on May 12, 2023
How a MA horse bettor's Kentucky Derby bets played out, from

The 2023 Kentucky Derby has come and gone, and the Preakness Stakes is up next.

Even with legal US sportsbooks live in Massachusetts, betting on the Preakness Stakes is still a major event for horse betting in Massachusetts.

Our Play MA writer and Massachusetts native, Jack Flaherty, took a look at what worked — and what didn’t work — from a betting perspective for the Kentucky Derby, plus a lookahead toward the Preakness.

Recapping the Kentucky Derby from a bettor’s perspective

The 2023 Kentucky Derby was won by Mage after a gutsy closing comeback. Mage had odds of 17-1 to win.

I, unfortunately, suffered a bettor’s nightmare: Two of my principal picks, Verifying and Kingsbarns, decided to kill each other. Verifying started in post 2 and evidently the strategy was to just blaze out and try to do a War Emblem. Go out front right away and just keep going as fast and as long as you can. Unfortunately, Kingsbarns decided to join and press him.

Together my pair ran dreadful fractions of 22.35 for the quarter and 45.73 for the half, which was way too fast. Both guys were soon cooked. It’s not easy to accomplish what War Emblem did. To his credit, Verifying’s jockey knew his pony was fried and eased him back early. Verifying is ready for a well-deserved rest.

The late scratch of the heavy favorite Forte spooked a lot of people.

It was the official track veterinarian and not the trainer who scratched him. Unusual.

How my Derby bets did

My Kentucky Derby bets didn’t do very well.

I put a late $10 win bet on Mage and that helped cut back my losses. I rely on my dominant wagers of win and place, but there is some drawback to that: In order to cash a ticket, your ponies actually have to come in first or second. Angel Of Empire came closest at third, but third does not pay off on place bets no matter how much you plead with the tellers.

Here are the recent 2023 Derby payouts:

  • The exacta (8-3) paid $330.44 on a $2 bet. Pretty damn good.
  • The trifecta (8-3-14) paid close to $982 for a $1 bet. 
  • The superfecta (8-3-14-11) paid $15,643 on a $1 dollar bet.

You can see why betting on the Derby is so popular.

I kick myself for not being more flexible after playing a bunch of $1 tri-boxes. Tri-boxes use three horses in any order and cost just $6. I had Mage and Angel in one, but not the third horse. I was using long-long shots in all my tri-boxes according to my protocol. But none of the deep long shots came close. 

I also used several tri-keys since I had a lot of faith in Angel Of Empire. In a tri-key (trifecta key bet), you have to key a horse to win on top, and then include two horses (or more) underneath to finish in any order. The trick is to get the winner on top right. 

A tri-key is inexpensive. You can play a $2 tri-key for just $4 (it’s only two combinations). However, no matter how cheap, my Angel did not win so down the chute I went.

A quick look at the forthcoming Preakness

We have three Derby starters slated to come, including Mage. The Mage connections have recently disassembled about shipping him to Baltimore, but Derby winners must compete in the Preakness. So I think he will. My cynical side thinks they are posturing for appearance money. Common for stars in other sports, but rare in horse racing.

Forte is out because of his 14-day vet suspension, but I recently read his trainer is appealing to get him into the race. We’ll see.

So we’re looking at potential runners to include:

  • Blazing Sevens                   
  • Chase the Chaos                 
  • Confidence Game                
  • Disarm                                 
  • First Mission                         
  • Mage                                    
  • National Treasure                  
  • Perform                                  
  • Red Route One  

Maybes include Ultimate Gamble, Coffeewithchris and some others.

The Preakness limits its field to 14.

Photo by AP Photo/Julio Cortez
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Jack Flaherty

Jack Flaherty independently represented manufacturers in the Middle East and Africa for 29 years and is a lifelong horse racing fan who, on two occasions, successfully bribed the National Guard with cheap beer and hopped the fence to attend the 1974 and 1975 Kentucky Derby. Jack currently resides in Falmouth, Massachusetts.

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