Asmussen Teams With Smith and Santana Seeking Derby Win

Heading into the 2010 Kentucky Derby Presented by Yum! Brands (G1), trainer Todd Pletcher was winless in the classic from 24 starters. So he turned to a cagey, successful Derby jockey, giving Calvin Borel the ride on Super Saver  , one of his four entries that year.

The eventual Hall of Fame jockey worked his Derby magic, hugging the fence on a sloppy racetrack on the WinStar Farm-owned runner. Super Saver splashed his way to victory at Churchill Downs, giving Pletcher the first of his two Derby wins (followed by Always Dreaming   in 2017), while Borel notched his third Derby victory in a four-year period.

Now Hall of Fame trainer Steve Asmussen, seeking his first Derby win, is giving a leg up to another multiple Derby-winning rider, Mike Smith, with hopes he can lead one of his 3-year-olds to Derby success. Smith will ride Winchell Thoroughbreds' Midnight Bourbon , one of the trainer's two entries, while Asmussen's regular go-to rider, Ricardo Santana Jr., retains the mount on Erv Woolsey and Keith Asmussen's Super Stock .

Smith has won the race twice, first on late-running longshot Giacomo  in 2005 and then on Triple Crown winner Justify   in 2018. 

"I'm 0-for-21 in the Derby and Mike isn't," Asmussen quipped of seeking out the rider.

Specifically, Smith is 2-for-26 with four seconds and a third. 

Asmussen views the veteran rider's skills as a good fit for Midnight Bourbon, who won the Lecomte Stakes (G3) this winter on the lead and later hit the board in the Risen Star Stakes Presented by Lamarque Ford (G2) and Twinspires.com Louisiana Derby (G2) after pressing the early pace.

"I just strongly feel Midnight Bourbon is in position. We're there. You know, he's been away from the gates nice and clean. He's got a big rhythm. Horse's got excellent pace to him," the trainer said. "We've all witnessed Mike with those attributes at this level."

Asked by Camilla Yakteen in a recent interview on XBTV.com what it is like to enter the first turn in the Derby, Smith explained that it depends on the style of runner.

"When I was on Justify it was pretty sweet. Man, we were in front. He was in a high, yet a nice cruising speed," he said. "I've also been back in that second flight, where I mean it's like playing the game of ping pong, almost. I mean you're just getting knocked back and forth, you know."

Possessing speed, Midnight Bourbon should be clear of the thickest Derby traffic—provided he breaks well, which is vital in the Derby, according to Smith.

"You would think going a mile and a quarter if you missed the break, you'd be OK. That's a death sentence. I mean, nine times out of 10," said the Hall of Famer, whose slow-starting mount in 2020, Honor A. P.  , rallied belatedly for fourth.

According to Smith, 55, who teamed with Asmussen previously as the rider of 2019 champion older female Midnight Bisou , the Derby is regularly a scramble for early position.

"They don't ride it like it's a normal mile-and-a-quarter race," he said of his fellow jockeys. "They literally ride it like—to me, it's ridden a lot like a 440-yard race for the first 100 yards out of there, and then everything settles into place afterwards."

Though not as experienced as Smith in the Derby, Santana has ridden in the Derby six times, mostly for Asmussen. His best finish was a fifth last year on Max Player , a colt who served as a workmate for Super Stock April 24 when they breezed five furlongs in tandem at Churchill in 1:01 1/5.

Santana, 28, has in recent years earned Asmussen's and his owners' faith with the trainer's best stakes horses.

Four or five years ago, it was not uncommon for him to be replaced on certain high-profile stakes runners. Santana rode WinStar Farm and Bobby Flay's Creator  in the 2016 Derby, in one example, guiding him to 13th-place finish, but he was replaced by Irad Ortiz Jr. in the Belmont Stakes Presented by NYRA Bets (G1), a race Creator won by a nose.

"Tremendous amount of talent and effort, which I think the most impressive thing from equines and human is effort," Asmussen said of Santana. "He's putting it together. The last few years, you know, multiple Breeders Cup wins—it's time for him to win a classic. He obviously has (the) talent level that is well within him to do so."

The 2016 Belmont is one of three American classics won by Asmussen, the others being the 2007 Preakness Stakes (G1) with Curlin   and the 2009 Preakness with Rachel Alexandra .

Though Asmussen has twice had horses run second in the Derby (Nehro , 2011, and Lookin At Lee  , 2017), show finishes in the Derby from Curlin and Gun Runner   are editions that Asmussen regards as ones that may have gotten away. Curlin and Gun Runner would go on to earn more than $10 million and $15 million, respectively, and would both win Horse of the Year titles, Curlin at 3 and 4 and Gun Runner at 4.

He attributes those editions as not "meant to be."

"I think that the Derby more than any other horse race I've ever witnessed seems to be more of an event than a race. It really does. Not yet—was kind of our situation," said Asmussen, who will also saddle 3-year-old fillies Clairiere  and Pauline's Pearl  in the April 30 Longines Kentucky Oaks (G1) at Churchill. "Obviously everything feels extremely positive right now. Couldn't be any more pleased with how this group is traveling."