A Motivated Search for Derby Longshots

By J. Keeler Johnson ("Keelerman") Twitter: @J_Keelerman

The Kentucky Derby is just nine days away, and the field is pretty much set. All that remains is to watch workouts, review replays, decipher data, and come up with our selections.

In years past, I've taken this week before the Derby to highlight live longshots worth considering for exotic wagers. Many have finished off the board (my apologies!), but there have been a few live ones along the way.

Without further ado, let's highlight three (hopefully live) longshots with the potential to outrun expectations in the 2021 Kentucky Derby:

Highly Motivated

The undefeated Essential Quality will be favored to prevail in the Kentucky Derby; final odds around 3-1 ought to be in the offing. So isn't there some appeal to playing Highly Motivated at 10-1 or so, considering he finished just a neck behind Essential Quality in the Blue Grass (G2)?

If there's one horse I'm confident is primed for a career-best effort on the first Saturday in May, it's Highly Motivated. If I may, allow me to repost a few paragraphs I wrote about Highly Motivated prior to his performance in the Blue Grass:

...Highly Motivated is conditioned by Chad Brown, who has done masterful work prepping horses like Highly Motivated to peak during the spring of their sophomore seasons. A few examples include:

  • Normandy Invasion, beaten a nose in the 2012 Remsen (G2) as a juvenile. After coming back with a slightly dull fifth-place effort as the 3-2 favorite in the 2013 Risen Star (G2), Normandy Invasion improved sharply in his second run of the season, finishing second by less than a length in the Wood Memorial (G1). Finally, Normandy Invasion ran the race of his life in the Kentucky Derby (G1), rallying prematurely to seize command in a fast-paced race before weakening slightly to finish fourth.
  • Practical Joke, whose two-year-old campaign included wins in the 2016 Hopeful (G1) and Champagne (G1) plus a third-place effort in the Breeders' Cup Juvenile (G1). Practical Joke's sophomore debut was rather unremarkable—he was beaten 5 3/4 lengths when second in the 2017 Fountain of Youth (G2). But Practical Joke improved in the Blue Grass (G2), finishing second by less than a length, and later outran expectations (and his pedigree) to finish a game fifth in the Kentucky Derby at 27-1.
  • Good Magic, the champion two-year-old of 2017 after winning the Breeders' Cup Juvenile (G1). One of the greatest upsets of 2018 came when Good Magic was beaten at 7-10 in the Fountain of Youth (G2), his first start as a sophomore. But Good Magic improved significantly off that effort, winning the Blue Grass (G2) before finishing second behind Triple Crown winner Justify in the Kentucky Derby.

I'm rehashing these details because Highly Motivated performed to script in the Blue Grass, carving out the pace before finishing fast (final three furlongs in :36.45) to give Essential Quality a stiff battle to the wire. This marked a big step forward off Highly Motivated's 2021 debut, when he received a tricky trip in the Gotham (G3) and settled for a non-threatening third.

Highly Motivated will be making his third start off a layoff in the Kentucky Derby, just like Normandy Invasion, Practical Joke, and Good Magic. He showed substantial improvement in his second prep run, just like Normandy Invasion, Practical Joke, and Good Magic. And he's exiting the Blue Grass, just like Practical Joke and Good Magic. Surely Highly Motivated is poised to produce his best effort yet in the Kentucky Derby?

I understand why some folks question whether Highly Motivated can handle the Derby's 1 1/4-mile distance; after all, he's bred for speed, and Essential Quality caught him fair and square in the Blue Grass. But Highly Motivated's pedigree isn't any more speed-oriented than that of 2020 Kentucky Derby winner Authentic (they actually share the same sire), and if Chad Brown can prepare a sprinter/miler like Practical Joke to outrun all expectations and finish fifth in the Kentucky Derby, I'm inclined to believe Highly Motivated can rise even higher.

Truthfully, I'm tempted to make Highly Motivated my top choice in the Kentucky Derby. But we'll have to wait until next week to see where I finally settle!

O Besos

I'm not sure how big a longshot O Besos will actually be, since everyone (myself included) seems to have identified him out as a live contender at a nice price. But even at 20-1 or so, the son of 2013 Kentucky Derby hero Orb is well worth playing.

After all, O Besos has shown promising and improving form since stretching out in distance. After rallying to finish fourth in the 1 1/8-mile Risen Star (G2), O Besos improved to third in the 1 3/16-mile Louisiana Derby (G2), a performance that was solid any way you slice it. Saving ground around the second turn, O Besos rallied boldly from seven to third place, beaten just two lengths while sprinting the final three furlongs in an excellent :37.29.

Only three Kentucky Derby contenders (Essential Quality, Highly Motivated, and Known Agenda) managed to finish faster than O Besos in their final prep, which bodes well for his chances on Derby Day. O Besos reminds me a lot of 2017 Arkansas Derby (G1) third-place finisher Lookin At Lee, who finished second at 33-1 in the 2017 Kentucky Derby after bringing the fourth-fastest final three-eighths fraction to the Derby field.

Lookin At Lee, of course, benefited from a ground-saving journey in the Run for the Roses; in fact, the Equibase result chart called it a "dream ins trip to 1/8," or a dream inside trip to the eighth pole. I hope to see O Besos employ similar tactics, since he's already shown in the Louisiana Derby that he doesn't mind rallying up the rail. An inside post would surely help O Besos receive the trip he needs to crash the Kentucky Derby superfecta at a solid price.


I'll be the first to admit there are plenty of obstacles standing between Sainthood and victory in the Kentucky Derby. He went unraced as a two-year-old... he's unproven against stakes company on dirt... he's yet to run particularly fast on the speed figure scales... you get the picture.

But I do believe Sainthood is better than he appears at first glance. Just check out his effort in the Jeff Ruby Steaks (G3) over the synthetic Tapeta track at Turfway Park. After tracking the leaders while racing inside, Sainthood got bottled up in traffic at a key point on the far turn, losing an opportunity to advance. Then, when he attempted to steer outside for racing room, he got bumped, blocked, and bounced around in traffic.

Sainthood could have called it quits, but instead, he re-rallied boldly to fall a length short of victory. Conditioned by two-time Kentucky Derby-winning trainer Todd Pletcher, Sainthood had previously displayed impressive tenacity to win a 1 1/16-mile maiden special weight over the dirt track at Fair Grounds, battling back after losing the lead to win by a nose.

Sainthood might not be the most likely winner of the Kentucky Derby, but he has the pedigree to handle 1 1/4 miles, and he may start at around 50-1 in the betting. At that price, Sainthood is worth including in exotic wagers. At least we know he won't give up if he runs into traffic!

Now it's your turn! Which Kentucky Derby longshots have caught your eye?


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J. Keeler Johnson (also known as "Keelerman") is a writer, videographer, voice actor, handicapper, and all-around horse racing enthusiast. A great fan of racing history, he considers Dr. Fager to be the greatest racehorse ever produced in America, but counts Zenyatta as his all-time favorite. He is the founder of the horse racing website www.theturfboard.com.

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