🐎 Kentucky Derby 2025: My Handicapping Breakdown for the 151st Run for the Roses

A Tradition Like No Other… and You Know I Had to Weigh In

May 03, 2025

Hey everyone!

Normally, I save Saturdays for a Deep Dive, but I’m switching it up this weekend. Those of you who’ve been riding along with me for a while know I started working at a greyhound racetrack back in high school and stayed there into my early 20s before I ever sat behind a trading desk. It was loud, fast, and gritty—and honestly, not that different from the NYSE Trading Floor. That experience taught me how to read odds, spot value, and understand momentum in ways that still help me today.

And if you’ve been around, you also know how much I love the most exciting two minutes in sports—the Kentucky Derby. So today, I'm doing something a little different: I'm handicapping the 151st Run for the Roses and giving you my take on who might shock the field and who might disappoint.

So grab a Mint Julep 🥃🌿 and let’s dive in!

🏁 The 2025 Kentucky Derby Lineup

Odds as of May 3rd (Scratches Noted)

1. Citizen Bull (16-1)
2. Neoequos (53-1)
3. Final Gambit (16-1)
4. Rodriguez (SCR)
5. American Promise (12-1)
6. Admire Daytona (37-1)
7. Luxor Cafe (13-1)
8. Journalism (7-2)
9. Burnham Square (18-1)
10. Grande (SCR)
11. Flying Mohawk (34-1)

12. East Avenue (31-1)
13. Publisher (28-1)
14. Tiztastic (18-1)
15. Render Judgment (12-1)
16. Coal Battle (27-1)
17. Sandman (5-1)
18. Sovereignty (10-1)
19. Chunk of Gold (31-1)
20. Owen Almighty (40-1)
21. Baeza (34-1)

🔍 The Horses Grabbing Headlines

Journalism (7-2) – The morning line favorite. Trained by Michael McCarthy, he's riding a four-race win streak and has the speed to justify the hype. But favorites only win about 40% of the time at the Derby. A stalking style could get him into trouble if the early pace collapses or the field backs up.
Sandman (5-1) – Strong closer with a lot of fans. If the front runners burn each other out, Sandman will be flying late. Some sharp handicappers have him as their top pick.
Sovereignty (10-1) – One of the strongest closers in the field and could get the perfect setup if the race goes fast early. I like his style and his timing.
Burnham Square (18-1) – Quiet value pick. Winner of the Blue Grass and improving with every race. One of the few with solid Churchill experience.
Flying Mohawk (34-1) – The wild long shot. He's still figuring things out, but there’s some real upside if the distance suits him and the pace melts.

🧠 My Derby Take

You know I approach everything like a trader—risk/reward, probability, trend. So here’s how I see it:

Journalism is fast, but I’m not betting the favorite at 7-2. The reward just isn’t there in a 20-horse stampede. The pace scenario is chaotic, and that makes me lean toward closers who can swoop in late after the front runners tire out.

Out of all the closers, Sovereignty jumps off the page for me. He’s got Derby bloodlines, and if this pace falls apart (and I think it will), he’s built to capitalize.

If I’m taking a swing on value, I’m backing Burnham Square—he’s peaking at the right time, has experience on this track, and could surprise everyone if the race breaks right.

And if you're a fan of bombs, I wouldn’t talk you out of tossing Flying Mohawk into your superfecta ticket.

🏆 My Picks:

Sovereignty (10-1)
Burnham Square (18-1)
Sandman (5-1)
Journalism (7-2)
Flying Mohawk (34-1)

🎯 Betting Strategies

🏇 Strategy 1: The Conservative Approach – Just Want Action

Small risk, big fun. Total Budget: ~$20–$30

$5 Win/Place on Sovereignty (10-1)

If he wins or comes second, you collect.

$1 Exacta Box – Sovereignty, Sandman, Burnham Square

Total cost: $6
You win if any two of them run 1st and 2nd in any order.

$0.50 Trifecta Box – Sovereignty, Sandman, Burnham Square

Total cost: $3
Any combo of those three running 1st-2nd-3rd.

🎲 Low cost, multiple shots at a decent payout if Sovereignty hits.

💰 Strategy 2: The Value Play – Looking for a Score

Mid-range budget with value in mind. Total Budget: ~$50

$10 Win on Sovereignty

You believe he’s the best closer and will get the setup.

$5 Win on Burnham Square

Improving form + value = solid upside.

$1 Exacta Box – Sovereignty, Sandman, Burnham Square, Journalism

Total cost: $12
Covering all 1-2 finish combos among your core four.

$0.50 Trifecta Box – Sovereignty, Sandman, Burnham Square, Journalism

Total cost: $12
Looking for 3 of the 4 to hit the board in any order.

🎯 More coverage, and still enough leverage to make it count if the favorite gets upset.

🧨 Strategy 3: Go Big or Go Home – The Bomb Hunter

Aggressive plays for serious bragging rights. Total Budget: ~$100

$20 Win on Sovereignty
$10 Win on Burnham Square
$5 Win on Flying Mohawk (34-1)

If the bomb lands, you’ve got bragging rights for years.

$1 Trifecta Key – Sovereignty on top, with Sandman, Burnham Square, Journalism, Flying Mohawk underneath

Cost: $12
You need Sovereignty to win, and the others to fill out 2nd and 3rd.

$0.50 Superfecta Box – Sovereignty, Burnham Square, Sandman, Flying Mohawk

Total cost: $12
All four must finish in the top 4 in any order.

$1 Exacta – Sovereignty over Sandman, Burnham Square, and Journalism

Cost: $3
You need Sovereignty to win and one of the others to run second.

💥 This is the trader who bets on earnings crushes and moonshots. Risky, but the reward could be massive.

📝 Final Thoughts

Favorites rarely win, and chaos is part of what makes the Derby so fun to bet. Whether you’re looking for value, playing it safe, or swinging for the fences, there’s a strategy here that fits. Just like in trading, define your risk, find your edge, and let the probabilities play out.

🏁 Who are you betting on? Let me know below or hit reply!

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Disclaimer: Everything I share in The Options Oracle is my opinion, not financial advice—even when it's about horses. 🐎

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