Everything You Need to Know About This Year’s Unusual Kentucky Derby

What to look for at this Saturday’s much-anticipated running

Photo: Coady Photography

Medina Spirit.

The Kentucky Derby slips back this year in its rightful place as the keystone of the South’s rites of spring, and it’s a most welcome rebirth. For their part in all this, Thoroughbred racehorses haven’t quite gotten the memo that there has been a pandemic, so they just want to race, and that unstoppable natural power is a bracing gate-opener to the month of May, and to the rest of the Triple Crown season. The reserved seats at Churchill Downs this Friday and Saturday for the Kentucky Oaks and the Derby will be reduced by 50 percent, but that, in comparison to the almost wholly deformed 2020 racing season, is a victory in Louisville, and for spectator sports.

The unflappable Arizona horseman and legendary Hall of Fame trainer Bob Baffert—whose mounts have won a record six Kentucky Derbies, seven Preakness Stakes, three Belmonts, and two Triple Crowns—arrived on Monday, April 26, trackside at Churchill with his 2021 contender Medina Spirit, who was out for a maintenance gallop. Baffert’s most recent Derby victory was last year with Authentic, a running that was postponed from May until September, making it a short seven-month span between the 146th Derby and the 147th. “I was hoping to enjoy my Derby win a little longer,” the trainer joked, “but it’s always great to be back at Churchill Downs.”

Famous for introducing unexpected top-tier horses to the nation through the Derby, Baffert is quite realistic about his mount’s chances on Saturday, rating him in the top ten of the twenty-horse field. “He’s run second to some really nice horses,” Baffert added. “He’s doing well over this track.” The horseman’s rule is that anything can happen in a Kentucky Derby, and often does, but, loosely translated, Mr. Baffert is saying that he could, just, wind up in the money. But he doesn’t have the favorite.

In addition to its occasion—the jolly display of hats, the sweat beading on the julep cups, the flare of the buglers calling the horses to the track—for the horses, the Derby is a more warlike rite of spring. Although most have raced in their second year, they are, with these storied stakes, being introduced to the nation and the world, and not least, to each other. The Class of 2021 has produced more than a handful of favorites from among the three-year-olds for the 147th running of the Derby, among them, the aptly named Hot Rod Charlie, Essential Quality, Rock Your World, Highly Motivated, and Midnight Bourbon.

As the late March and early-April prep races got underway, the undefeated Essential Quality was the leading favorite, but he only won his last key prep, the Blue Grass Stakes at Keeneland on April 3, by a neck.  The horse that nearly took him at the wire was Highly Motivated, who is a contender Saturday afternoon. From the way he ran in the Blue Grass, Highly Motivated is thought to have a splendid chance to sneak up and steal Essential Quality’s thunder.

photo: Coady Photography
Essential Quality at the Blue Grass Stakes.

That’s not the only intramural frisson in this field. The clear “big boy” is the very aptly named Rock Your World, who, in the post-position draw on April 27, drew what the horsemen call the “15 hole,” or the fifteenth stall in Churchill’s vast, twenty-horse gate. That is one stall to the right of Essential Quality, in post position fourteen. (The rule in racing, especially in the Derby’s traditional twenty-horse fields, is that everybody will be pushing toward the rail to get position and save ground.) Highly Motivated, Essential Quality’s other major rival, is three stalls to the right, at seventeen. In short, Essential Quality, who is only the favorite by a bit, has his two deadliest competitors to his outside. It means he has to have a perfect start. 

In a word, unlike last year’s heavily asterisked running, the race is hot. It can play out to be hotter than that. Herewith, an early picture of the field, with each horse’s post position and early odds to win.

Post Position — Horse, Morning Line

1 — Known Agenda, 6-1
2 — Like the King, 50-1
3 — Brooklyn Strong, 50-1
4 — Keepmeinmind, 50-1
5 — Sainthood, 50-1
6 — O Besos, 20-1
7 — Mandaloun, 15-1
8 — Medina Spirit, 15-1
9 — Hot Rod Charlie, 8-1
10 — Midnight Bourbon, 20-1

11 — Dynamic One, 20-1
12 — Helium, 50-1
13 — Hidden Stash, 50-1
14 — Essential Quality, 2-1
15 — Rock Your World, 5-1
16 — King Fury, 20-1
17 — Highly Motivated, 10-1
18 — Super Stock, 30-1
19 — Soup and Sandwich, 30-1
20 — Bourbonic, 30-1

By definition, because of the prep races before the Derby, however lightly they’ve raced, the three-year-olds entered in the Derby are experienced horses. But this year all of them are inexperienced in one special way that will matter to them: No matter how tough the preps have been that they have run as two- and three-year-olds, all of them have only run under pandemic spectator-sport protocols. The public has not been allowed at racing meetings for the last year—which was the crucial first year of racing for this crop of Thoroughbreds.

The upshot is, the majority of this Derby field has never run in front of a crowd. Even at 50 percent capacity, a Kentucky Derby is a blaring charivari of color, light, and noise. Even in a normal Derby year (which 2021 is not), a factor in the paddock and on the track before the race is what the horsewomen and horsemen call the Derby Freak-Out Factor. Some young horses just can’t take it, and melt down in the race.

To help us parse how this massive crush of athleticism will deal with these and other hurdles, we’ll call now on our longstanding and most generous Kentucky horseman, the Bluegrass Wise Man™, who last appeared in this space to explain the inner workings of the 2020 Breeders’ Cup. The Wise Man, well-known in his home state, prefers to remain anonymous so as not to unduly influence the tote. At least, that’s what he says to us. 

So, you’re just gonna tell me to bet Baffert, right, Medina Spirit all the way?

Anybody betting on Medina Spirit had better have a bunch of other fancy tickets featuring Hot Rod Charlie, Rock Your World, Essential Quality, Highly Motivated, Known Agenda, and on and on. It’s a big race this year, some good competition in there well above Medina Spirit’s pay grade, which we need, obviously. [Jockey] “Big Money Mike” Smith is on Midnight Bourbon, which automatically makes him more dangerous. More the merrier, all that. Everybody’s been racing, but been a bit of a dry spell with fans…

photo: Coady Photography

Stop right there. You’re famous for your freak-out theory about the Derby. Give us your take on the specialness of that this year.

Lemme put it this way: You haven’t lived until you’ve had a horse get their brains fried so they run last in the Derby. This year, I’m not sure how many of ’em have even ever raced with fans, but not many. Point is, what does 50 percent mean? Fifty percent of who’s in the stands, so twenty thousand people? Thirty thousand? It’s still a ton of people, and they’re gonna be happy to be there, out in the springtime, at the race. None of these horses have ever seen that, and they’re just three, right? I mean, Rock Your World, who’s a top horse, has only raced three times. I can guarantee you that he’s never seen anything like this.

Okay, let’s assume whatever meltdowns there are let them make it to the gate. Bear down on the Derby’s famous crush. This is your shot to tell us about post positions.

The crush is about traffic. It’s not just that the horses have never run in the Derby, or in front of a crowd. None of them have ever run in fields this big. It means a lot of things. The run to the first turn is a quarter mile, which, with a field of seven to ten would be plenty of room. If you basically double the number of runners, which the Derby will do, that room gets cut dramatically. Given that, everybody’s going to want to save ground, so they tend to break in and come down on whoever’s inside. Whoever’s drawn the inside at the Derby has their work cut out for them. They have to get out there quick. The secondary risk with a lotta traffic is, if you survive the break but don’t get to where you might like to be, then you have to dig back up through the traffic on the backstretch to even have a hope around the far turn. Sometimes, that just gets to be too much for them, and it wears ’em out.  What it boils down to is that trainers and jockeys don’t much like drawing the rail or the heavy inside post positions, because if you don’t get a good break, which sometimes happens, everybody and their mother comes down on you and you drown.  

Coverage starts Saturday, May 1, on NBC at 2:30 p.m. The Kentucky Derby is scheduled to be run at approximately 6:57 p.m.