Daily to Derby: Jerry Bailey and Randy Moss Join the Monster Pod (Friday, May 1, 2026)

Jerry Bailey and Randy Moss Join the Monster Pod — and It’s Our Biggest Video of Derby Week

Thirty thousand 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?

🏇 Oaks Night — Primetime on NBC

For the first time in its 152 year history, the Kentucky Oaks goes off in primetime. NBC’s coverage starts at 4 PM ET on Peacock, with the main broadcast at 8 PM ET on NBC. Post time is 8:40 PM ET. Fourteen fillies.

I wrote a full horse-by-horse guide to the Oaks for Sky Sports Racing / At The Races. My verdict: Zany on top despite the defeat last time — the Ashland was better than it looked, and Pletcher has won this race four times. Always A Runner is the most appealing alternative because of her ceiling and late speed. And Meaning stays on side as well. I’ll play those three in exactas and have a goofy longshot to throw in the mix.

👉 Read: Horse-by-Horse Guide: Kentucky Oaks (At The Races)

Also live on ATR this week:

👉 Horse-by-Horse Guide: Kentucky Derby

👉 Horse-by-Horse Guide: American Turf Stakes

👉 2026 Kentucky Derby Preview

🌍 For International Viewers

For Sky Sports Racing viewers in the UK, Ireland, and beyond — the Oaks is live at 1:40 AM on Saturday morning (Sky 415 / Virgin 512). The Derby is live tomorrow night at 11:57 PM. All of my ATR previews are live now and free to read.

🚨 Field Update — Final (Probably)

Two scratches this week: Silent Tactic (bruised foot) and Fulleffort (bone chip). Great White and Ocelli drew in. The field is locked at 20. No further changes expected.

Updated odds as of Thursday evening: 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’s move from 15-1 ML to 6-1 is the market story of the week.

🌧️ Weather

Rain hit overnight Wednesday and more is possible today. Chad Brown moved Emerging Market’s final work up to beat it. If we get a wet track tomorrow, that changes the handicapping. We’ll update in the morning.

📄 Free Derby Contender Profiles — 19 Live

👉 Browse all contender profiles

📋 ICYMI

👉 Why You Can’t Bet the Derby on Kalshi (ITM Original)

👉 Can You Win the Derby From the Rail? (ITM Original)

👉 Is Todd Pletcher Actually Bad in the Derby? (ITM Original)

👉 Derby OddsWatch — updated April 26

👉 Final Answers — The Full Show from Lexington

👉 Sean Boarman’s Derby Day Breakdown — Plus subs get the full LP5 picks

👉 Great White Monster Pod

👉 Brad Cox Monster Pod

👉 Monster Pod Full Compilation — every horse, 2+ hours

👉 Free Bris Derby PPs (PDF)

🥃 Derby Dram No. 5

Woodford Reserve Double Oaked Single Barrel, Barrel Proof — Barrel 0389

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

Woodford’s Double Oaked process takes their standard bourbon and finishes it in a second barrel — heavily toasted, lightly charred — designed to amplify the wood sweetness that defines the expression. Most Double Oaked pours rich and sweet. Barrel 0389, selected November 2025, didn’t read the script. This single cask at 94.86 proof skews dry and tannic in the most interesting way. Dark fruit runs through everything — dried plum, dried orange peel, a persistent leather note — with vanilla present but muted, playing support rather than lead. The toasting process usually produces sweetness; here it produced structure. Pleasantly atypical for the style, 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.

❓ Today’s Open Question: It’s Oaks Day. The fillies go first. Who do you like tonight — and are you using the Oaks to set up your Derby Day Pick 6?

Previous editions: Edition 21: Final Answers, Two Scratches, and Kalshi · Edition 20: Can You Win the Derby From the Rail? · Full archive