Keeler Johnson's Kentucky Derby 147 Selections

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

After a couple of frustrating misses in recent years, you might say I'm highly motivated to pick the winner of the 2021 Kentucky Derby (G1) at Churchill Downs. Preferably a winner who isn't the top betting choice.

I was among the handicappers who selected Maximum Security to win the 2019 Kentucky Derby, and for about 20 minutes, I thought I'd picked the right horse. But Maximum Security was ultimately disqualified for causing interference on the far turn, and my luck in 2020 was no better. I thought Tiz the Law was a lock to win the famously postponed edition of the "Run for the Roses," but after challenging for command at the top of the stretch, Tiz the Law settled for second place.

I'm eager to get back to the satisfying (though admittedly uncreative) string of success I enjoyed between 2014 and 2018, when four of my five Kentucky Derby selections visited the winner's circle. California Chrome, American Pharoah, Nyquist, and Justify were all favorites, but at least they were profitable plays.

If you had asked me two weeks ago to name the 2021 Kentucky Derby winner, I would have steered you toward #1 Known Agenda (6-1). On paper, I think the stoutly bred son of Curlin is formidable. Conditioned by two-time Kentucky Derby-winning trainer Todd Pletcher, Known Agenda has improved dramatically since adding blinkers two starts back. After dominating a Gulfstream Park allowance race by 11 lengths, Known Agenda blew the Florida Derby to pieces with a powerful sprint to the finish line, dashing the final three furlongs in :36.59 to score by 2 3/4 lengths.

But in the two weeks since, I've wavered in my support for Known Agenda. I'm still a little concerned about the greenness he's displayed throughout his career. In the Sam F. Davis (G3), back before he wore blinkers, Known Agenda fell far off the pace and refused to engage until much too late, when he came flying hard to finish fifth. And even in the Florida Derby, Known Agenda had difficulty maintaining a straight course down the lane, initially drifting out before shifting back in again.

I don't think drawing the rail will be an issue for Known Agenda, who raced inside for much of the Florida Derby before shifting out for his rally. But I do wonder if the chaos of the 20-horse Kentucky Derby field will bring out some of Known Agenda's greenness again, compromising his chances at victory.

Two weeks ago, if I had talked myself out of Known Agenda, I certainly would have sided with #14 Essential Quality (2-1). What's not to like? The undefeated Kentucky Derby favorite brings a perfect 5-for-5 resume to the table, including a pace-pressing victory in the Blue Grass (G2) last time out. He finished faster than any other Kentucky Derby contender in his final prep run, rocketing the final three furlongs in :36.34, and has shown versatility when it comes to running style.

But Essential Quality has also been on the top of his game for months—he was voted champion two-year-old male of 2020 after winning the Breeders' Futurity (G1) and Breeders' Cup Juvenile (G1) in succession. It can be difficult for young horses to remain atop their division for more than a few months, since growth spurts and the magic of maturity can rapidly shift the pecking order. Essential Quality did win the Blue Grass, but he was all-out to catch pacesetter Highly Motivated by a neck.

There's one other concern I have with Essential Quality, and that's the fact he paddles with his left front leg. This stride abnormality hasn't been an issue for Essential Quality so far, but as a general rule, paddling can make it difficult for horses to stretch out over extended distances. There's a part of me that wonders if the 1 1/4-mile journey of the Kentucky Derby will prove challenging for Essential Quality to negotiate, especially if he receives a tricky trip. In the Blue Grass, Essential Quality had the benefit of pressing a slow pace from second place—he couldn't have asked for a more relaxed run. But Essential Quality tends to fall farther behind in fast-paced races, and since the Kentucky Derby typically unfolds at a solid tempo, I think he'll be left with a lot more to do around the far turn and down the homestretch at Churchill Downs.

So if I've talked myself out of Known Agenda and Essential Quality, where have I landed? You guessed it; I'm going to give #17 Highly Motivated (10-1) a try. I actually made my case for Highly Motivated last week, diving deep into his credentials as a live longshot. To read my reasoning in detail, check out "A Motivated Search for Derby Longshots."

To recap in brief, I'm confident Highly Motivated has been perfectly prepared to produce a career-best effort in the Kentucky Derby. Trainer Chad Brown has done masterful work preparing horses like Highly Motivated for the Run for the Roses, favoring a two-prep approach that places a definite emphasis on the "prep" aspect. Winning early-season Derby qualifiers isn't the goal; in fact, the three horses Brown has saddled to earn purse money in the Kentucky Derby went a combined 1-for-6 during their winter/spring prep campaigns.

But Brown's horses have historically been ready to roll on the first Saturday in May, and Highly Motivated appears to be progressing down the same path. He kicked off 2021 with a third-place effort in the Gotham (G3) at Aqueduct, and while he did seem a bit short of his best, he nevertheless battled through a tricky trip to finish just 1 3/4 lengths behind the winner.

Then came the Blue Grass, where Highly Motivated took a big step forward. Finding himself in the unfamiliar position of setting the pace, Highly Motivated led most of the way and fought on gamely when challenged by Essential Quality, ultimately succumbing by just a neck while sprinting the final three furlongs in a rapid :36.45.

For the Kentucky Derby, Highly Motivated has drawn post 17, setting the stage for a perfect trip. He won't have to carve out the pace this time; he can let gate-to-wire Santa Anita Derby (G1) winner #15 Rock Your World (5-1) take up the task instead, giving Highly Motivated a target to chase. In recent years, this has been the ideal trip for Kentucky Derby winners, with California Chrome (2014), American Pharoah (2015), Nyquist (2016), Always Dreaming (2017), and Justify (2018) all employing this strategy.

So there you have it—for the first time on Unlocking Winners, I'm picking a Derby horse who won't be the first or second choice in the betting. I can't promise victory if you follow me into these uncharted waters, but at least I can guarantee a fun ride. No matter what happens, we'll have a shot at a big payday.


#17 Highly Motivated (17-1)


#1 Known Agenda (6-1)

#9 Hot Rod Charlie (8-1)

The Louisiana Derby (G2) winner has made steady progress for two-time Kentucky Derby-winning trainer Doug O'Neill, who utilized a two-prep approach to win the roses with I'll Have Another (2012) and Nyquist (2016). Hot Rod Charlie is following the same path and finished less than a length behind Essential Quality in the Breeders' Cup Juvenile last fall, so we know he has the class to compete at this level.

#14 Essential Quality (2-1)

#15 Rock Your World (5-1)

The gate-to-wire Santa Anita Derby (G1) winner looks like the "speed of the speed" on paper, and since he's only run once on dirt (and has no experience facing kickback), I have to think he'll employ front-running tactics again in the Kentucky Derby. He didn't race as a juvenile and has questions to answer from a foundation standpoint, but speed is always dangerous, and Rock Your World is one of the fastest horses on paper.


#4 Keepmeindmind (50-1)

The Breeders' Cup Juvenile third-place finisher is dropping blinkers, so he figures to take back and make one run. If he's able to save ground and slip up the rail, a top-four finisher isn't out of the question. We've seen less accomplished horses crash the Kentucky Derby superfecta.

#5 Sainthood (50-1)

He endured a significantly troubled trip when second in the Jeff Ruby Steaks (G3) and has room for improvement with a clean journey. Veteran Churchill Downs jockey Corey Lanerie takes the mount, and since Lanerie is never afraid to ride the rail with longshots (2017 Kentucky Derby runner-up Lookin At Lee comes to mind), I hope to see Sainthood work out a ground-saving trip.

#6 O Besos (20-1)

Saving ground also stands to produce a strong finish from O Besos, who rallied nicely up the Fair Grounds rail to finish third by two lengths in the Louisiana Derby (G2). He actually sprinted the final three furlongs in :37.29, the fourth-fastest finishing fraction posted by a 2021 Kentucky Derby contender in their final prep run.

#16 King Fury (20-1)

While King Fury did get a fast pace to work with in the Lexington (G3), he was also thoroughly dominant, rallying smoothly up the inside before splitting horses and drawing clear to win by 2 3/4 lengths. He may have trouble reaching the rail from post 16, but jockey Brian Hernandez has been highly successful at Churchill Downs and may give King Fury just the trip he needs to factor at a price.

Good luck!


Want to test your handicapping skills against fellow Unlocking Winners readers? Check out the Unlocking Winners contests page—there's a new challenge every week!


The Road to the Kentucky Derby handicapping challenge is back for the seventh straight year! Check out the Road to the Kentucky Derby contest page for more details.

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

Recent Posts

More Blogs