Daily to Derby

Cherie DeVaux, Chuck Simon, and the Moment That Changed Everything

At the post-position draw last week — before the race, before the history — Kali and the TwinSpires social team sat down with Cherie DeVaux. She talked about starting her career as the Oaks girl at Churchill Downs 22 years ago. She talked about a mentor she lost. And she said something that hits very differently now.

"Just keep going. And be yourself. There were times that I questioned this journey, this path. And luckily I always got brought back. You can't let the mistakes define you. You have to really look for the lessons. Even if it's a bad situation, there's always a lesson. As long as you can use that and implement it going forward in your life, then nothing you do is ever going to define you."

The mentor she was talking about was Chuck Simon.

Simon was a Saratoga Springs native, an Allen Jerkens protégé, and a horseman who won 359 races and over $11 million in purses before retiring in 2019. He hired Cherie in her early 20s and kept her for six years. Here's what she told TDN after he died: "Chuck is the whole reason that I am where I'm at this point in my life. He saw that I was going down the wrong path. He didn't force me to do anything I didn't want to do but he gave me direction and really took me under his wing. He was almost like a big brother."

Simon died on September 8, 2024, at 57, from Stage 4 cancer. Eight months later, the woman he pulled off the wrong path became the first female trainer to win the Kentucky Derby.

At the draw, DeVaux said Simon would have ribbed her mercilessly — their relationship was crude and honest, and he always joked that her superpower was marching to her own drum. "I think he'd be tickled to see me out here," she said.

After the race, she had a simpler observation: "I'm just glad I don't have to answer that question anymore."

(Full credit to Kali and the TwinSpires social team for the pre-Derby interview.)

The Road to Laurel Park — May 16

The Preakness picture is shaping up fast, and it looks nothing like the Derby. The key developments from Sunday morning:

Golden Tempo — On the table, not confirmed. DeVaux: "As long as he's in tiptop shape, we'll talk about it. It is on the table. But it's really up to him." If she runs him, she'd be the first female trainer to win both the Derby and the Preakness. Four of the last seven Derby winners skipped the Preakness entirely — including last year's winner Sovereignty.

Renegade — No Preakness. Pletcher confirmed Sunday: "He'll head to Saratoga on Tuesday. Play the Belmont by ear." The rematch, if it happens, waits until June 6.

Ocelli — Not likely despite running third at 70-1. Beckman says no Triple Crown pursuit. Still a maiden.

Crude Velocity — The Oddschecker favorite at 6/4. Destroyed the Pat Day Mile for Baffert. Connections said pre-race they'd target the Preakness. Sean Boarman singled him in the LP5 — "any pick fives would go through him and him alone." Now he's the horse to beat in Baltimore.

Also pointing to the Preakness: Chip Honcho (Asmussen, bullet work Derby Day), Iron Honor (Chad Brown), Ottinho (Chad Brown), Napoleon Solo (Summers, ships to Laurel May 10), Taj Mahal (Russell, already at Laurel, perfect 3-for-3), The Hell We Did (Fincher, already at Laurel), Cherokee Nation (Baffert), Silent Tactic (Casse, hoping to make it after Derby scratch).

This is the first Preakness at Laurel Park while Pimlico undergoes a $400 million renovation. Different track, different dynamic. We'll have a full preview as the field takes shape.

Oddschecker First Prices

Crude Velocity 6/4
Taj Mahal 6/1 · Silent Tactic 6/1 · Golden Tempo 6/1
Iron Honor 12/1 · The Hell We Did 12/1 · Chip Honcho 12/1
Great White 14/1 · Cherokee Nation 14/1 · Pretty Boy Miah 14/1
Napoleon Solo 16/1 · Ottinho 16/1

Notable absences: no Renegade, no Chief Wallabee, no Commandment, no Further Ado. The books are pricing a completely fresh field with Derby Day also-rans and shooters who skipped Churchill entirely.

24 Editions from April 10 to May 2

Every edition from the road to Derby 152 is here:

👉 Browse the full archive

And the three ITM Originals that defined our coverage:

👉 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?