Maximum Security, Improbable Face Off in Awesome Again

The field of five will also include last out allowance optional claiming winner Take the One O One, winner of the Charles Town Classic (G2) Sleepy Eyes Todd, and the dual graded winner Midcourt. 

Maximum Security holds the first spot in the Breeders’ Cup Classic rankings, while Improbable holds the fourth. The two went up against each other a year-and-a-half ago at Churchill Downs in the 2019 Kentucky Derby Presented by Woodford Reserve (G1), where Maximum Security was disqualified and moved from first to 17th for interference. 

In the Derby, Improbable moved up from fifth to fourth with the disqualification. 

The two runners are trained by Hall of Famer Bob Baffert, who only conditioned Improbable in 2019. It wasn’t until this spring the trainer got ahold of Maximum Security, who was transferred following the indictment of former trainer Jason Servis on doping-related charges in March.

The four-year-old New Year’s Day colt has taken two victories from two runs since then, including the San Diego Handicap (G2) July 25 at Del Mar. He also won by three lengths in the Aug. 22 TVG Pacific Classic Stakes (G1), a designated Breeders’ Cup qualifier that awarded him an automatic berth in the Classic.

"He's training really well. I'm happy with him," Baffert said. "He hasn't regressed or anything like that. I love the way he's moving."

Maximum Security is owned by Gary and Mary West, and the Coolmore-affiliated Susan Magnier, Michael Tabor, and Derrick Smith. 

With his Aug. 1 Whitney Stakes (G1) victory at Saratoga, Improbable also received a Classic berth. He won that race by a couple of lengths over By My Standards and Tom’s d’Etat. 

Because of this, the Awesome Again’s “Win and You’re In” aspect does not matter to the runners, but it is the home track of both of them. They do not need to ship, resulting in a six-week rest going into the Classic.

Improbable has traveled this year, shipping to Arkansas before finishing second to Tom’s d’Etat in the Oaklawn Mile Stakes. He also went to Saratoga to run in the Whitney and won the Hollywood Gold Cup (G1) at Santa Anita on June 6. 

The four-year-old son of City Zip is owned by WinStar Farm, China Horse Club, and SF Racing.

According to Baffert and Elliot Walden, who is the president and racing manager for WinStar, the two decided that the timing of the Awesome Again was a better option compared to other races like the Oct. 10 Jockey Club Gold Cup (G1) at Belmont Park. 

"He's always been a great athlete that skips over the ground," Baffert said about Improbable. "He's going to be tough. He's a good horse. But I think mentally, he's matured. Physically, he's matured."

Improbable will be joined by jockey Drayden Van Dyke, while regular rider Luis Saez will have the call for Maximum Security. 

Both of the runners carry high weight of 126 pounds, spotting the other entrants in the field between two and four pounds. 

The field will also include Midcourt, who could provide the biggest challenge to the duo. He finished a nose behind Maximum Security in San Diego and then third in the Pacific Classic. 

The five-year-old Midnight Lute gelding is owned by C R K Stable and trained by John Shirreffs.