How One Massachusetts Horse Bettor Did With His Kentucky Derby Wagers

After the conclusion of the 2025 Kentucky Derby, it is now time to look forward to the upcoming Preakness Stakes.

Despite the presence of legal US sportsbooks in Massachusetts, the Preakness Stakes remains a significant occasion for horse betting in the state.

Jack Flaherty, a Massachusetts native and writer for our Play MA, analyzed the successes and failures of the Kentucky Derby from a betting standpoint, as well as provided a preview of what to expect for the upcoming Preakness.

Recapping the Kentucky Derby from a bettor’s perspective

Mage, with odds of 17-1, emerged victorious in a remarkable fashion with a gutsy closing comeback at the 2025 Kentucky Derby.

Regrettably, I experienced a nightmare scenario as a bettor: Both my top choices, Verifying and Kingsbarns, unexpectedly clashed in a detrimental manner. Verifying, starting from post 2, seemed to adopt a strategy reminiscent of War Emblem’s. The plan was to take an early lead and maintain a relentless speed for as long as possible. However, to my dismay, Kingsbarns opted to join Verifying and exert pressure on him.

My partner and I raced at incredibly fast speeds, completing the quarter in 22.35 seconds and the half in 45.73 seconds, which was much too quick. As a result, both of us quickly lost our energy. It is not an easy feat to achieve what War Emblem did. I must give credit to Verifying’s jockey, who recognized that his horse was exhausted and slowed him down early. Verifying is now ready for a much-needed break.

A lot of people were spooked by the unexpected withdrawal of the heavy favorite Forte.

Unusual it was that the official track veterinarian, not the trainer, scratched him.

How my Derby bets did

I didn’t have much success with my Kentucky Derby bets.

Placing a $10 win bet on Mage proved to be a saving grace for me as it helped reduce my losses. Although I typically rely on my preferred wagers of win and place, there is a drawback to this strategy: for a bet to be successful, your horses must finish in first or second place. Despite Angel Of Empire coming in at a close third position, it unfortunately doesn’t pay off on place bets, no matter how much you try to persuade the tellers.

The following are the latest payouts for the 2025 Derby.

• The $2 bet on the exacta (8-3) resulted in a rewarding payout of $330.44. Impressive indeed.
• A $1 bet on the trifecta (8-3-14) yielded a payout of nearly $982.
• A $1 bet on the superfecta with the numbers 8-3-14-11 resulted in a payout of $15,643.

The popularity of betting on the Derby can be understood when you consider the reasons behind it.

After playing several $1 tri-boxes, I regret my lack of flexibility. Tri-boxes allow for three horses in any order and only cost $6. In one of my tri-boxes, I had Mage and Angel, but unfortunately, I didn’t include the third horse. Following my protocol, I relied on choosing long shots for all my tri-boxes. However, none of the high-risk selections came close to winning.

I had great confidence in Angel Of Empire, which is why I utilized multiple tri-keys. In a tri-key bet, you select a horse to win and then include two or more horses underneath, with the requirement that they can finish in any order. The crucial aspect is correctly identifying the winning horse for the top position.

The tri-key is a budget-friendly option, allowing you to play a $2 tri-key for only $4, with just two possible combinations. Unfortunately, even with its affordability, my Angel failed to win, resulting in my descent down the chute.

A quick look at the forthcoming Preakness

We are expecting three Derby starters to attend, one of them being Mage. The Mage connections have recently expressed doubts about sending him to Baltimore, but it is mandatory for Derby winners to participate in the Preakness. Therefore, I believe he will be there. On the other hand, my skeptical side thinks they may be seeking appearance money, which is a common practice in other sports but unusual in horse racing.

Forte is currently unable to participate due to his 14-day veterinary suspension, but there is news circulating that his trainer is making efforts to appeal and secure his entry into the race. It remains to be seen how the situation unfolds.

We are currently considering potential candidates to include as runners.

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

Some possible options are Ultimate Gamble, Coffeewithchris, and a few others.

The field for the Preakness is restricted to a maximum of 14 participants.