Sharp or Square - KENTUCKY DERBY BETTING PREVIEW

The Herd with Colin Cowherd37mApril 30, 2026

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AI-Generated Summary

In this episode of 'Sharper Square,' hosts Chad Millman and Simon Hunter welcome Mike Conte, a seasoned handicapper, thoroughbred owner, and Kentucky Derby expert, for a deep dive into the 152nd running of the Kentucky Derby. The conversation kicks off with Mike recounting his emotional and euphoric experience as an owner when his horse, Miss Call, won a race at Keeneland, highlighting the unique physical cues—muscle tone, coat shine, ear position—that signal a horse’s readiness. The hosts then pivot to a pressing issue: the growing influence of AI and computer-assisted wagering (CAW) in horse racing, which is giving professional syndicates a massive edge over casual bettors. Mike explains how real-time betting algorithms can lock in odds in milliseconds, drastically altering payouts and making it harder for average bettors to find value. Despite this, he remains optimistic, emphasizing the unpredictability of the Derby, where long shots have won as often as favorites in recent years. He highlights key contenders like the Puma, Chief Wallaby, and emerging long shot Dan and Bourbon, while sharing his own exacta key box bet centered on the Puma. The episode closes with a reminder that the Derby remains a cultural phenomenon, drawing both fans and professionals, though the latter treat it more as a public spectacle than a strategic goldmine.

Key Takeaways
1

AI and computer-assisted wagering are creating a massive advantage for professional syndicates, making it harder for average bettors to find value.

2

The Kentucky Derby is a once-in-a-lifetime race for three-year-old horses, with a 20-horse field, a mile-and-a-quarter distance, and unprecedented starting gate pressure.

3

Horse owners can spot strong contenders by physical cues: muscle tone, coat shine, pricked ears, and confident movement in the paddock.

4

Long shots have won the Derby as often as favorites in recent years—seven of the last seven winners included at least one long shot, with two at under 10-1 and two at 60-1 or longer.

5

Mike Conte’s top pick is the Puma (9), whom he believes has the form, pedigree, and jockey to win, with Chief Wallaby (12) and Emerging Market (15) as strong secondary options.

…and 2 more takeaways available in PodZeus

Chapters
0:00
8 min

Podcast Promos & Introduction

The episode opens with a series of iHeartRadio podcast promos for shows like The Clifford Show, 2%, Look Back At It, and Learn the Hard Way, followed by the official intro to Sharper Square, hosted by Chad Millman and Simon Hunter.

7:30
6 min

Mike Conte’s Ownership Experience with Miss Call

It was one of those moments where for those that have seen the movie Secretariat, the trainer is yelling at Ronnie Turcotte in the movie, Ronnie, don't fall off going for the wire and the Belmont. And that's kind of how I felt because we had such a big lead. I was like, Brian, just hang on to her.

Highlight
13:00
10 min

The AI Revolution in Horse Racing

When you have a horse that's paying 40 bucks in the sequence, no matter what else you had, I think you had two other favorites in that sequence. It's changed the game for the average better.

Highlight
22:30
13 min

The Kentucky Derby: Unique Challenges & Field Dynamics

Mike explains the unique challenges of the Kentucky Derby: a 20-horse field, a mile-and-a-quarter distance, a narrow starting gate, and the deafening crowd noise. He emphasizes that this is a one-time opportunity for each horse, making the race emotionally and physically intense.

35:00
28 min

Top Contenders & Betting Strategy

My top choice... is going to be the Puma. I think a horse, you know, again with a win over at the Tampa Bay Derby, ran really well in the Florida Derby just to get nipped at the wire by Commandment. I think that this is a horse that can continue to move forward as he has pretty much throughout his young life so far.

Highlight
High-Impact Quotes
My top choice... is going to be the Puma. I think a horse, you know, again with a win over at the Tampa Bay Derby, ran really well in the Florida Derby just to get nipped at the wire by Commandment. I think that this is a horse that can continue to move forward as he has pretty much throughout his young life so far.
Mike Conte36:31
Viral: 90.0
When you have a horse that's paying 40 bucks in the sequence, no matter what else you had, I think you had two other favorites in that sequence. It's changed the game for the average better.
Mike Conte11:17
Viral: 88.0
It was one of those moments where for those that have seen the movie Secretariat, the trainer is yelling at Ronnie Turcotte in the movie, Ronnie, don't fall off going for the wire and the Belmont. And that's kind of how I felt because we had such a big lead. I was like, Brian, just hang on to her.
Mike Conte5:33
Viral: 85.0
Speakers

Hosts

Chad MillmanSimon Hunter

Guest

Mike Conte
Topics Discussed
Kentucky Derby Betting Strategy95%AI and Computer-Assisted Wagering90%Horse Racing Physical Cues85%Thoroughbred Ownership Experience80%Long Shot Contenders75%Derby Field Dynamics70%Betting Pools and Takeout65%Jockey and Trainer Combinations60%
People & Brands

Mike Conte

person

18xPositive

Chad Millman

person

15xNeutral

Simon Hunter

person

14xNeutral

Miss Call

other

12xPositive

Puma

other

10xPositive

Chief Wallaby

other

8xPositive

Emerging Market

other

7xPositive

Dan and Bourbon

other

6xPositive

Hard Rock Bet

brand

5xPositive

Churchill Downs

organization

4xNeutral

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