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Can Winning Impression Be a Serious Challenger at the 2020 Kentucky Derby?

| September 3, 2020 3:45 am PDT
Can Winning Impression Be a Serious Challenger at the Kentucky Derby?

Throughout the season, Winning Impression has somehow managed to stay in the running for the 2020 Kentucky Derby, despite his final 20-point score on the KD leaderboard. He’s a late performer, they say, meaning he tends to discover speed only after half the track is behind him.

And it took the gelding three attempts to break his maiden. Now, that’s not exactly a rare occurrence among young racing thoroughbreds, but it doesn’t exactly inspire confidence in the future success of a Kentucky Derby hopeful.

Winning Impression’s Trainer

Dallas Stewart has taken horses to the Kentucky Derby twice (2012 and 2014), and to the Preakness twice (2008 and 2015). He also has a solid record with various members of the Unbridled progeny in Breeders’ Cup races.

Stewart seems to make a living turning “problematic” thoroughbreds into winners, but Winning Impression may prove to be a bridge too far for even him—as his disappointing also-rans in his final two KD qualifying races would indicate.

Winning Impression’s Jockey

Joe Rocco Jr. has his work cut out for him. While Julien Leparoux rode Winning Impression to his only RTKD points in the Arkansas Derby, he failed to repeat that performance at the Indiana Derby.

And so it was that Rocco was in the irons for Winning Impressions last run in a KD qualifier: the Ellis Park Derby. But again, Winning Impression failed to perform, racking up his second seventh-place finish in a row.

Still, Rocco has shown with his many graded stakes wins over the years that he knows what to do when life hands him lemons.

Winning Impression’s Recent Form

Winning Impression didn’t break his maiden until December of 2019, after two earlier attempts resulted in disappointing fifth-place finishes.

After that, he managed a second and a third in allowance races at Fair Ground. It wasn’t until early May 2020 in the Arkansas Derby that he put himself on the RTKD leaderboard with a fourth-place finish—later upgraded to third-place after the winner, Charlatan, was disqualified after he tested positive for an “above-threshold amount” of lidocaine.

That DQ changed Winning Impression’s RTKD score from ten to 20, and those 20 points comprise Winning Impression’s final Road score, which placed him at Number 18 on the KD leaderboard and assured his slot in the Kentucky Derby.

But Winning Impression and his connections didn’t know that at the time, so he returned to the track at the Indiana Derby in July, but pulled a seventh-place finish for his efforts.

And history repeated itself, unfortunately with a seventh-place finish in his final KD qualifier, the Ellis Park Derby in early August.

Why Winning Impression Won’t Win the Kentucky Derby

Early handicappers put Winning Impression’s chance in the KD at 150-1—and that sounds about right. With only one win—his maiden back in December 2019—the gelding has failed to finish in the RTKD scoring for two-thirds of his qualifying starts. And seventh place is not a “missed it by that much” sort of finish.

Those last two seventh-place finishes are a clear signal that while Winning Impression might have been able to get on the final roster to run the Kentucky Derby, he’ll be following most of his competition during the race itself—late speed or no.

Looking to bet on the Kentucky Derby online? Check out this guide.

J.W. Paine
J.W. Paine

J.W. Paine is one of the most experienced writers at GamblingSites.com. He's written for television and the printed media, and is a published novelist (as Tom Elliott).

Paine loves writing about Las Vegas nearly as much he loves living here. An experienced gambler, he's especially familiar with thoroughbred horseracing, poker, blackjack, and slots.

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