Daily to Derby — Jerry Bailey and Randy Moss Join the Monster Pod

Kentucky Derby 152 · Road to Churchill Downs

Your morning briefing on the road to the Kentucky Derby

Edition No. 22 · Friday, May 1, 2026

🎙️ MONSTER PODCAST

Jerry Bailey and Randy Moss — 30K Views in 21 Hours

NBC's Jerry Bailey and Randy Moss sat down with PTF and JK for the Kentucky Derby Best Bets show — and it became the biggest ITM video of Derby week by a wide margin. If you haven't watched it yet, what are you waiting for?

▶ Watch: Derby Best Bets with Bailey and Moss →

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🏇 OAKS NIGHT — PRIMETIME ON NBC

Kentucky Oaks Goes Under the Lights

For the first time in its 152 year history, the Kentucky Oaks goes off in primetime. NBC at 8 PM ET. Post time 8:40 PM ET. 14 fillies.

My verdict for Sky Sports Racing / At The Races: Zany on top, Always A Runner as the value play, Meaning on side. I'll play those three in exactas and have a goofy longshot to throw in the mix.

👉 Horse-by-Horse Guide: Kentucky Oaks

👉 Horse-by-Horse Guide: Kentucky Derby

👉 Horse-by-Horse Guide: American Turf Stakes

👉 2026 Kentucky Derby Preview

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🌍 FOR INTERNATIONAL VIEWERS

Oaks live at 1:40 AM Saturday (Sky 415 / Virgin 512). Derby tomorrow at 11:57 PM. All ATR previews live and free.

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🚨 FIELD UPDATE — FINAL (PROBABLY)

Two scratches: Silent Tactic, Fulleffort. Great White and Ocelli in. Field locked at 20.

Updated odds: Renegade 9-2 · So Happy 6-1 · Commandment 7-1 · Further Ado 7-1 · The Puma 8-1 · Chief Wallabee 9-1 · Emerging Market 11-1 · Danon Bourbon 14-1

So Happy from 15-1 ML to 6-1 is the market story of the week.

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🌧️ WEATHER

Rain possible today. If we get a wet track tomorrow, that changes the handicapping. We'll update in the morning.

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📄 FREE CONTENT

👉 Browse all 19 free contender profiles

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📋 ICYMI

👉 Why You Can't Bet the Derby on Kalshi

👉 Can You Win the Derby From the Rail?

👉 Is Todd Pletcher Actually Bad in the Derby?

👉 Final Answers — Full Show

👉 Sean Boarman's Derby Breakdown — Plus subs get full LP5 picks

👉 Monster Pod Full Compilation — every horse

👉 Free Bris Derby PPs (PDF)

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🥃 DERBY DRAM No. 5

Woodford Reserve Double Oaked Single Barrel — Barrel 0389

MSRP ~$75 · 47.43% ABV / 94.86 proof · Versailles, KY

Woodford's Double Oaked process takes their standard bourbon and finishes it in a second barrel — heavily toasted, lightly charred. Most Double Oaked pours rich and sweet. Barrel 0389 didn't read the script. This single cask skews dry and tannic — dried plum, dried orange peel, a persistent leather note — with vanilla present but muted. The toasting usually produces sweetness; here it produced structure. Pleasantly atypical, and a reminder that single barrel variation is real and worth chasing.

Tomorrow we close out Derby Dram week with two: Maker's Mark turned up to 11 — the Cellar Aged is what happens when you give Kentucky's most iconic bottle more time and more proof. And the one you've been waiting for all week: Pappy Van Winkle 15 Year on the biggest day in horse racing. See you at the finish line.

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