For many years, the Kentucky Derby featured fields ranging from seven to eleven horses. Trainers and owners didn’t run unless they felt they had a horse that belonged. When Captain Bodgit, a horse I co-owned, ran second in 1997 he was in a field of 13. But over the past two decades, field sizes have swelled to the maximum of 20 and owners of three year old horses scrambled to qualify for the race. Being in the race became the goal; not winning it. People are into experiences and there are very few experiences that can match having a horse in the Derby. The “walkover” from the barn to the paddock on the track in front of 145,000 people has become an iconic moment. I sure won’t forget my walkover with Went the Day Well when he ran fourth in 2012.

But things are changing again. This year, many owners of horses that qualified for the Derby are skipping the race. In the end, only 20 even entered. My theory? With Covid eliminating many of the race activities and the number of participants in the walkover, the experience iust isn’t the same and owners of horses with little chance aren’t wasting their time. So what, you say? The end result this year is a field that includes about ten also-rans. Given that the overall field is weak from top to bottom, it creates a situation in which I believe you can safely eliminate more than half the horses. Picking the Derby winner is a matter of pride. But if you bet correctly, having the winner in a group of four or five can suffice.

Essential Quality, with five wins in five starts, will be favored. He’s trained by Brad Cox, a guy who wins everything in sight while raising suspicions about how he does it. His owners, the rulers of Dubai, are obsessed with winning the Derby and this is their best chance to finally get that first win. California-based Rock Your World is the wild card. He’s run only three times but crushed his fields in all three. His first two races were on grass before he crushed in the Santa Anita Derby. It used to be folly to think such a lightly raced horse could win. But then Justify won the Triple Crown in 2018 after only three prep races.

Bob Baffert? He appeared loaded with three year old a couple of months ago but all but one has fallen by the wayside. That horse, Medina Spirit, is a nice horse but doesn’t appear to be one of the best. On the other hand, Baffert can never be discounted in the Derby.

I’ll assess all 20 horses in post position order. Note: for logistical reasons I will not be able to update these picks should any scratches occur. If it happens, just eliminate the horse from wagers and move up the next contender.


#1 KNOWN AGENDA —The #1 post position is virtually death. It’s almost impossible not to get banged around and lose all position out of the starting gate from that post and Churchill’s unique configuration for 1 ¼ mile races. This horse won the Florida Derby, is trained by Todd Pletcher and has real ability. But until somebody wins from the one hole, I’m not picking anybody who starts from it.

#2 LIKE THE KING—I don’t Like the King.

#3— BROOKLYN STRONG—he made it in only because eight horses with more qualifying points were held out of the race.

#4 KEEPMEINMIND—This horse was better last year as a two year old but his trainer has a ridiculously high win percentage that has raised eyebrows.

#5 SAINTHOOD—Todd Pletcher trainee got in by winning a race on an artificial surface. That race was recently given top Derby qualifier status because the track is now owned by the company that owns Churchill Downs.

#6 O BESOS—There are a zillion reasons this horse can’t win. He’s never won a stakes race. He last ran in the Louisiana Derby, the prep race that never ever produces horses that do anything in the Kentucky Derby. His jockey is ordinary. BUT!!!!!! This horse’s speed figures have improved in all five of his races. He ran a 2 on the Thoro-Graph sheets and that’s faster than all but four horses in this race have ever run. He is one of the few who will relish the marathon Derby distance. He is a tremendous closer who will get a rapid pace up front to run at. His trainer, while low profile, is very good. His workouts over Churchill have been outstanding. He’ll need a crafty ride and some racing luck, but he’s a longshot with a huge chance to pull a shocker and win the Kentucky Derby. If I’m wrong, my apologies. But I’m backing this horse with my own money and think he represents compelling value.

#7 MANDALOUN—He was the heavy favorite in the above mentioned Louisiana Derby but faded badly. I think the Louisiana Derby was the strongest of all the prep races (which it never is until this year) and this horse could rebound.

#8 MEDINA SPIRIT—Bob Baffert trains him so he must be considered. Baffert has gotten away with more junk in his career that any 200 other trainers combined. Still, this horse has a tendency to lose ground in the stretch. On the other hand, he has faced strong competition and is ridden by the great John Velazquez.

#9 HOT ROD CHARLIE—What a great name. He won the Louisiana Derby which, as stated before, usually means nothing. But as I’ve been saying, I think that race was loaded this year. The Lou Derby is seven weeks before the Kentucky Derby and, in the past, that was too much of a layoff. But in today’s horse racing, good horses race less than ever. The trainer, Doug O’Neill, won the Derby in 2012.

#10 MIDNIGHT BOURBON—This is the other longshot that could win. He’s 20-1 in the program but he ran a strong second in the Louisiana Derby, the race I am apparently obsessed with this year. He’s never been worse than third in seven starts. The layoff probably helps him because he ran a lot of races early in his career. I am blown away by his workouts over Churchill Downs which I believe are the best of any of the 20 horses in the field. The horse’s regular rider was dumped so they could get aging Mike Smith. He barely rides anymore but still gets mounts in big races and is nicknamed “Big Money Mike.” I think Smith is a negative because he rides like he’s scared and keep his horses needlessly wide. But he’s a great judge of pace. This horse should get a perfect trip laying about four or five off the early lead and that’s usually the best way to win the Derby. If he does, you can celebrate at midnight with a bourbon.

#11 DYNAMIC ONE—Pletcher trainee who had run slowly in all of his starts but ran second in the Wood Memorial over a weird and tiring track at Aqueduct.

#12 HELIUM—Every year there’s a Derby horse I can’t figure out. Helium could win or he could run last. He won the Tampa Bay Derby the same day my Untreated ran lights out in a maiden race at the same Tampa track. Our horse ran faster in his race. Unfortunately, he’s on the shelf with an injury and Helium is here. Like I said, I don’t know what to do with him and can offer no insight on his chances.

#13 HIDDEN STASH—All of his races have been way too slow to win the Derby.

#14 ESSENTIAL QUALITY—-The unbeaten favorite. He has an ideal running style and will probably be about seventh or eighth in the early going. He’s sired by Tapit, the most dominant classic sire in America. Jockey Luis Saez is very aggressive and would have won the Derby two years ago had his horse not been disqualified. He has a major chance but he just doesn’t seem that much better than several others and he had a very hard race in his last start. He’s a legitimate, but vulnerable, favorite.

#15 ROCK YOUR WORLD—His first two races were on turf and he won them both. He was training so well on dirt they ran him in the Santa Anita Derby. He cruised to victory. He might be a freakish superstar and lightly raced horses have fared well in recent years. Rider Joel Rosario, who is one of the best two jockeys in the country, chose to get off of Hot Rod Charlie to ride this horse. Joel’s agent is very sharp. This horse had all of his timed workouts in California so it’s been harder to gauge him at Churchill Downs this week but he is an obvious win contender.

#16 KING FURY—Ran fast to win a lesser Derby prep three weeks ago. His trainer has pulled off lots of shockers in his day and the jockey is very competent and underrated. He’s a borderline contender with some positives and a few more negatives.

#17 HIGHLY MOTIVATED—Lost by a nostril to Essential Quality in the Blue Grass Stakes last out and has three excellent races in a row. Trainer Chad Brown is overdue to win the Derby. This is clearly one of the best horses in the race but I didn’t like his appearance on the track this week at Churchill. He needs to be considered in wagers but I have him in the second of four or five tiers of horses here.

#18 SUPER STOCK—He won the Arkansas Derby in dominant fashion four weeks ago and trainer Steve Asmussen is one of the best. Amazingly, he has improved in every one of his eight starts. The trainer here is important. When Asmussen’s horses get good, he has a knack of having them stay good. The wide post position doesn’t help but toss this horse out at your peril.

#19 SOUP AND SANDWICH—Identical story to #12 Helium. Same trainer. Again, only three races and all were good. But he’s a horse who needs to run close to, or on, the lead and the wide post position really hurts those kinds of horses as they have to be pushed hard to avoid being hung out wide in the first turn. I’m leaning against.

#20 BOURBONIC—Two horses with Bourbon in their names this year. This one, trained by Pletcher, won an unimpressive Wood Memorial and had to run in a claiming race just to break his maiden. On the other hand, he’s improving and is bred to get the distance and will be running late.


#6 O Besos 20-1
#10 Midnight Bourbon 20-1
#15 Rock Your World 5-1
#9 Hot Rod Charlie 8-1
#14 Essential Quality 2-1
#18 Super Stock 30-1


If I’m wrong it’s because I’m overrating this year’s Louisiana Derby. Historically, it is the Derby prep race that produces nothing but also-rans. But the game is changing and rest is more important than ever. The speed figures from all the services that track these things came back very strong. So the top three from that race are in my top five. Rock Your World is a possible freak but we won’t know for sure until late afternoon Saturday. Essential Quality, the favorite, has to be included.

There is a fair amount of early speed in the race and that should give the stalkers and closers a shot. I wish O Besos had a better jockey because working out a trip from the very back of the pack in a 20-horse rodeo is very hard. Midnight Bourbon will get a better trip but I lack confidence in his rider also. In a weak field, none of these horses is close to perfect. But two of them are likelier to go off at prices way higher than they ought to. That’s where I’m landing. If I’m wrong, I’ll never pay attention to the Louisiana Derby again.


First of all, I encourage you to consider everything on your own and craft your own bets. If you want to blindly follow me, I’m listing several wagers here appropriate for various budgets. They are listed in order of how much I like them. On some bets, bet size can be moved up or down according to your budget.

$20 to win win place and show on #6 and #10 ($120)
$1 trifecta 6-10 over 6-9-10-14-15-18 over all ($180)
50-cent trifecta 6-9-10-14-15-18 over 6-10 over all ($90)
$2 exacta box 6-9-10-14-15 ($40)
$2 exacta 6-10 over all ($76)
$1 exacta All over 6-10 ($38)


On Churchill Downs’ Saturday card, I also like:
#5 Tap It to Win (8-1) in Race 10, The Churchill Downs Stakes
#9 Ride a Comet (5-1) in Race 11, the Turf Classic


In Friday’s race for three year old fillies, I like #1 Pauline’s Pearl (20-1). In terms of value, she is compelling.

Suggested $1 Oaks Derby Double: 1-6-10-12-14 with 6-9-10-14-15-18 ($30)


Most of the OTBs are still closed or restricted. You can bet legally online. I strongly encourage you to only use legal US-based sites. While I won’t endorse any, all of the following are fine and easy to use: Xpressbet, Twin Spires, TVG, NYRA Bets, DRF Bets.

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