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The Herd with Colin Cowherd

Sharp or Square - KENTUCKY DERBY BETTING PREVIEW

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PodcastThe Herd with Colin Cowherd
Publisher/creatoriHeartPodcasts and The Volume
Published
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About this episode

One of America's most cherished Rites of Spring, the 152nd running of the Kentucky Derby is this Saturday at Churchill Downs in Louisville, Kentucky. This is the perfect event for sports fans and gamblers looking to turn a small investment into a big payday, with limitless opportunities and a massive parimutuel pool. To help them build some winning Kentucky Derby slips, betting expert Chad Millman and professional gambler Simon Hunter welcome back one of their favorite annual guests, effervescent horse racing handicapper Mike Conti.  Together they discuss what makes "The Most Exciting Two Minutes In Sports" unique as both a sporting event and betting bonanza, and how to approach betting a race of this magnitude. Mike Conti provides guidance on how to wisely build your exactas and trifecta tickets and manage your bankroll, and which thoroughbred horses he will be tossing from consideration. Top contenders Renegade, Commandment, Further Ado, Chief Wallabee, and The Puma will be in the starting gate for this Run For The Roses, and famous trainers Todd Pletcher and Bob Baffert are once again in the mix. We also get our guests's expert picks and predictions for the Kentucky Oaks, and several other races taking place at Churchill Downs on both Friday and Derby Day. Plus, a fascinating breakdown of how Artificial Intelligence is revolutionizing the horseracing side of parimutuel betting. #Volume  0:00:00 - START 0:08:00 - HOW A.I. IS REVOLUTIONIZING HORSE RACING 0:18:00 - WHAT MAKES THE KENTUCKY DERBY UNIQUE 0:26:57 - FAVORITE DERBY LONGSHOT HORSES 0:29:19 - KENTUCKY DERBY BEST BETS & EXACTAS -- All lines provided by Hard Rock Bet Subscribe to Sharp or Square for gambling advice, best bets, and predictions from sports betting experts Chad Millman and Simon Hunter. Follow on all platforms: https://www.instagram.com/sharporsquare/ https://x.com/SharporSquare_ See omnystudio.com/listener for privacy information.

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Episode summary

Welcome back to Sharper Square. Derby weekend is here, they’re running for the roses, and we’ve got our favorite horse‑handicapper and Ithaca football legend, thoroughbred owner Mike Conti, in the chair.

You just watched your filly Miss Call win at Keeneland. What did that feel like from paddock to winner’s circle?

Pure adrenaline. She looked sharp in the paddock on a sloppy track after a layoff, Brian Hernandez tipped her out, she opened up by daylight, and it felt like a once‑in‑a‑lifetime rush I want to chase again.

When you say a horse looks good in the paddock, what are you seeing?

Shiny coat, good muscle, fluid walk, ears forward, on her toes—confident body language that says she’s ready, though it still has to translate once the gate opens.

Miss Call surged clear late and hit the wire first for Brian Hernandez Jr., with rivals chasing for minor awards.

Quick detour: there’s an AI‑driven money boom in horse betting. CAW teams are hitting pools fast, and casual players at smaller tracks face a real disadvantage. Mike, how are you seeing it heading into the Derby?

It’s changed the everyday game. On routine cards, payouts feel compressed and odds can halve late, so I mostly play bigger days where their impact is softer; without a central governing body, rules lag and the average player gets squeezed.

For listeners, parimutuel means you’re betting into a pool, so your price moves until the race starts. With AI placing money in milliseconds and massive global handle, does that dampen the experience for you?

CAW has exploded over the last few years and tracks need that liquidity because of takeout—around twenty percent in the win pool—so it’s complicated; it keeps lights on but narrows edges for most bettors.

It’s Whisper Wednesday. What are you hearing from the backstretch?

Dan and Bourbon, the Japanese runner, has trained like he belongs; The Puma is taking early money; Silent Tactic scratched, so Great White draws in and outside posts slide one stall in; Emerging Market has been catching eyes in the morning.

How much does post matter with this huge field and all that Derby chaos?

It’s a once‑ever shot for three‑year‑olds, often their first try at a mile and a quarter, with twenty in a tighter gate and a wall of crowd noise; trip matters more than usual, and they must handle the moment.

Run us through the top five on the board.

Renegade in the one hole closes hard off the Arkansas Derby but needs a clean trip; Commandment, the Florida Derby winner, gets Luis Saez after top riders opted elsewhere; The Puma is lightly raced with upside, Mage vibes, and nearly beat Commandment; Chief Wallaby had traffic in the Florida Derby and brings back last year’s winning trainer‑jockey combo; Further Ado freaked in the Blue Grass with a big figure, though that prep hasn’t been as predictive lately.

Recent winners include shockers and mid‑priced runners. Any long shots worth a look?

Dan and Bourbon has distance and form at a price; So Happy brings tactical speed out of the Santa Anita Derby; Emerging Market is ultra‑lightly raced off the Louisiana Derby and could make history if he pulls it off.

What’s on your betting card?

Top pick is The Puma; I’ll also build around Chief Wallaby, who should sit a better trip with a rider who just won this race.

Do professionals treat Derby like the Super Bowl?

Pros chase edges wherever their models work best; the Derby is a spectacle I love to bet, but day‑to‑day grinders often prefer softer, local pools.

Agreed. It unites casuals and diehards, but pros still hunt the best overlays rather than the biggest stage.

Give us your exotics before we wrap.

Exacta key box with The Puma on top or second, paired with Commandment, So Happy, Chief Wallaby, Emerging Market, and Further Ado.

When’s Miss Call back, and how can listeners get into ownership?

She runs Friday at Churchill in race three, and we like her more than the morning line; newcomers can try syndicates to learn the ropes, and smaller groups give you more say with the barn.

We’re riding with Miss Call. Mike Conti, congrats and thanks for the Derby breakdown. This is Sharper Square—watch on YouTube, rate and review, and we’ll see you after the fastest two minutes in sports. Love you.

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