In the March 2019 Rebel Stakes at Oaklawn Park, Improbable overcame a wide trip, took command at the top of the stretch – then was run down by Long Range Toddy. A month later at the Arkansas Derby, Improbable overcame a wide trip, drew even with Omaha Beach, but couldn’t pass him.

Improbable at BC Dirt Mile
Improbable could be a probable winner of Saturday’s Oaklawn Handicap, but the talented horse needs to overcome starting and finishing issues. (Image: Coady Photography/Churchill Downs)

Fast forward to this year’s Oaklawn Mile Stakes on April 11. Improbable got out wide after acting up in the gate, seized the lead at the top of the stretch, and again, got caught and passed midstretch — this time by Tom’s d’Etat.

Detect a trend here? Hall of Fame trainer Bob Baffert and the rest of Improbable’s connections would like to think otherwise heading into Saturday’s $600,000 Grade 2 Oaklawn Handicap. The track’s premier race for older horses and one of Oaklawn’s feature races on closing day, the 1 1/8-mile handicap fits in between the Arkansas Derby’s two divisions as the 12th race on the 14-race card.

Improbable owns four victories and three seconds in his 11 starts – with all three seconds at Oaklawn. He’s closing in on $1 million in career earnings ($949,520). He won his first three races as a 2-year-old, including a five-length dismantling of the field in the Grade 1 Los Alamitos Futurity in December 2018.

From Derby Favorite to Preakness Disappointment

That stamped Improbable as a probable Kentucky Derby contender. When Omaha Beach scratched the week of the Derby, Improbable vaulted to the morning-line favorite. And even after finishing fifth, promoted to fourth when Maximum Security was disqualified, Improbable entered the Pimlico gate for the Preakness as the favorite.

His Equibase Speed Figures and pedigree (the son of the late City Zip) illustrate a horse who should finish what he starts.

Improbable’s talent all adds up. So what’s keeping him from the winner’s circle? Why has he won just one race in 17 months, that being the Grade 3 Shared Belief Stakes at Del Mar last August? Why did he finish a poor sixth as the Preakness favorite? A well-beaten fifth in the Breeders’ Cup Dirt Mile at Santa Anita last November?

And why is a horse with this much talent only 8/1 in the Oaklawn Handicap?

Improbable’s Gate-Crashing Issues Frustrate Baffert

One big reason is Improbable’s well-chronicled gate issue. Improbable is a starter’s nightmare, acting up in the gate at the Preakness and in the Pennsylvania Derby, where – once again – he went off as the 6/5 favorite, yet finished fourth in the six-horse race.

“I don’t know why he does it,” Baffert told reporters after the race. “He doesn’t do it in California. (Jockey) Mike (Smith) said he was really good and then heard a noise and it set him off. It’s just bad luck. It is very frustrating when you go that far and he pulls that stuff.”

Improbable “pulled that stuff” again in the Oaklawn Mile Stakes, getting fractious in the gate before turning in what Baffert called “a winning race.” Gate antics aside, it was probably Improbable’s best race since his 2-year-old season.

Positive Vibes Coming Into Handicap

“He got beat by a really good horse,” Baffert told Oaklawn’s Jennifer Hoyt. “His gate issues, I don’t know why … you take him in the morning and you could set a bomb off in the gate and he won’t move. He knows. He’s smart. That’s the reason I left him there (in Arkansas). That gate crew is getting to know him and I think that’s going to help.”

For the second consecutive race, Improbable drew the outside post, meaning jockey Martin Garcia has one more issue to contend with. Now, add in Improbable’s talented 4-year-old counterparts like Tacitus and By My Standards, and favorite Combatant coming off a Santa Anita Handicap win.

Once you throw in his recent races at Oaklawn and the aforementioned gate issues, Improbable has a lot of plates in the air. The question is, can he overcome his starting-gate and finishing-wire issues and finally crash the Oaklawn winner’s circle before any of them hit the ground?