Imaginationthelady Gives Dettori Double Jessamines

October 3, 2025

Imaginationthelady swept to the front for the victory. (Courtney Snow/Past The Wire)

Opening Day of Keeneland Fall Meet

Keeneland Release

LEXINGTON, Ky. – Imaginationthelady swept to the front of a tight pack at the sixteenth pole to score a 1-length victory over Infinite Sky to give jockey Frankie Dettori back-to-back wins in the Jessamine Presented by Keeneland Sales.

Trained by Brendan Walsh, Imaginationthelady completed the mile and a sixteenth on a firm turf course in 1:42.61 and earned a fees-paid berth to the $1 million John Deere Breeders’ Cup Juvenile Fillies Turf (G1) on Oct. 31.

Lit Ship led the field of 11 through fractions of :22.43 and :47.70 while Dettori, who won last year’s race on May Day Ready, had Imaginationthelady outside of horses and racing in mid-pack.

Lit Ship carried her lead into the stretch but was soon confronted by a wave of challengers with Imaginationthelady getting the first jump on the late runners.

A Keeneland sales graduate, Imaginationthelady is a Kentucky-bred daughter of Not This Time out of the War Front mare Romanticism. Now 2-for-2 in her career, Imaginationthelady increased her bankroll to $331,400.

Imaginationthelady returned $22.16, $11.08 and $5.46. Infinite Sky, ridden by Luan Machado, returned $17.38 and $7.04 and finished a nose in front of favored Time to Dream, who paid $2.64 to show under Irad Ortiz Jr.

It was another neck back to Soloist with Lit Ship, Aggressive Lime, Carolyncaroline, Loveliest, Red Beretta, Mackinac and Victor Help Me following in order.

Racing continues on Fall Stars Saturday with an 11-race program beginning at 1 p.m. ET and featuring five graded stakes, three of them Grade 1s.

Frankie Dettori (winning rider of Imaginationthelady): “Brendan (Walsh, the trainer) quietly was quite confident, and I thought, ‘I’m just going to ride a positive race.’ I knew there was a bit of speed, and I didn’t want to go four wide. I managed to slot her in behind the leaders, and I got to teach her something: to relax. Then I crept my way through the bend and swung her out. She’s a big filly with a big stride, so I gave her an eighth of a mile to get organized and then she took off. She’s got lots of potential.”

Dettori gets back-to-back Jessamine Stakes. (Courtney Snow/Past The Wire)
Dettori gets back-to-back Jessamine Stakes. (Courtney Snow/Past The Wire)

Brendan Walsh (winning trainer): “I was quietly confident. We liked her before she ran the first time (in a maiden special weight at Kentucky Downs Sept.  4), and she won, and she’s been improving since. So it was a question of how much she was improving — typical 2-year-old — but she ran a very nice race (today). (Jockey) Frankie (Dettori) was able to wait as long as he could, and like he said, he gave her a good education, and I’m sure that will stand her down the line.”

On whether she goes to the John Deere Breeders’ Cup Juvenile Fillies Turf (G1): “Obviously you wait to see how she comes out, but if everything goes right, I can’t see why not.”

Luan Machado (rider of runner-up Infinite Sky): “We had a little bit of trouble leaving the gate. The horse inside of me came out and got us pretty good. A little bit of stopping in the first turn and (from there) it was a perfect trip. I believe I had the best filly in the race today. I was very proud of her performance and the way she tried for me. The whole team, we are very happy with her.”

Irad Ortiz Jr. (rider of third-place finisher and beaten favorite Time to Dream): “I had a good trip. There was traffic. I waited a little too long, and it cost me the race.”

Todd Pletcher (trainer of Time to Dream): “She got a good trip into the first turn, even though she was further back than we wanted to be. (Irad Ortiz Jr.) was able to save ground, but then turning for home he had nowhere to go, blocked in and bumping around. Just got free too late but closed well when she did.”

Breeders’ Cup still under consideration? “Absolutely.”

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