I’ m Generating These 8 Bets, Longshot Picks To the 2023 Kentucky Derby

The 149th running of the Kentucky Derby is upon us.

With a little help from my friends, I am going to give you the lowdown on this year’s race: a preview of several strong favorites and a healthy second tier of ponies that are capable of an upset.

The Kentucky Derby distance is 1 1/4 miles on dirt. A furlong is 1/8 of a mile. This is the first time our battling 3-year-olds will have run as far as 10 furlongs, so distance pedigree or parentage is one of the many things I, as a fellow Massachusetts horse race betting enthusiast, take into consideration.

Usually, 20 horses compete. This year, we’ll have just 20 horses racing. There were some scratches and the full field of 20 replacements used.

So, before I reveal my picks, here’s everything you need to know about each of the horses in the Kentucky Derby. Below, I’ve listed the post number, horse, trainer, previous race result, and projected odds. The number in parentheses is the horse’s best Beyer Speed Figure, a rating system to gauge the fastest a horse has ever run in its career.

Note: Since publication, Known Agenda, Soup and Sandwich, Like the King, Bourbonic, and O Besos all scratched for various reasons. There were only three replacement horses – King Fury, Keepmeinmind, and Brooklyn Strong – so 17 horses will run.

Kentucky Derby 2023 horses together with trainers

1. Hit Present (93)

Trainer: Brad Cox

Last race: Wood Memorial (2nd)

Odds: 26-1

Unless your horse is a speedster who likes to break out in front early, the 1-post position puts horses at a disadvantage. The last Derby winner from the 1-post was Ferdinand in 1986. There are two races in the Derby – the start and the race to the first turn. After that, you hope your horse is in a good position and can settle down and run as close to the rail as possible, taking the shortest path around the track.

I’m not sure if Hot Rod Charlie can do that. His best performances this year were at Aqueduct, but I doubt the Churchill Downs officials would move the race there this week. He’s trained by Brad Cox, but I think I’ll stay away.

2. Validating (99)

Trainer: Brad Cox

Last race: Blue Grass Stakes (2nd)

Odds: 17-1

More bad news for Cox: The 2-post is not better than 1. There used to be a time when the outside posts were considered disadvantageous, but not anymore. We have had several recent winners from the outside, like Justify last year from post 20, Big Brown from post 20 in 2008, and Country House from post 18 in 2019, among others.

Right now, I would take post-19 over post-2. But that won’t deter me from Betting on Essential Quality. People have liked him all year. He finished a strong fourth in the slop at the Rebel, despite encountering a difficult trip. But Essential Quality never quits. The Keeneland fans were treated to a thrilling stretch drive recently between Essential Quality and Highly Motivated in the Blue Grass Stakes.

Essential Quality was a close second, and Cox has had several more weeks to train him up. This colt has heart, and I am betting on him anywhere on my FanDuel Racing Ma app.

3. Two Phil’s (101)

Trainer: Lewis Rivelli

Previous race: Rob Ruby (1st)

Odds: 7-1

From experience, I usually prefer cheap races and figures that work on a synthetic surface such as the new Tapeta synthetic surface at Turfway. However, this bias has also led me to overlook Derby winners like Animal Kingdom in 2011 and Lil E. Tee in 1992. Not to mention Preakness winners Summer Squall and Althea Bayou.

No, Two Phil’s is legit, but the horse is ridden by a jockey named Loveberry. Where did he come from? Move on.

4. Self-confidence Game (94)

Trainer: J. Keith Desormeaux

Last race: Rebel Stakes (1st)

Odds: 17-1

Won Rebel last in the mud in February. But that was in the past. I wonder why Desormeaux didn’t give him another race. I get easily scared when it comes to the Derby. Especially when I think a horse is being stagnant. But what do I know? The trainer had earned enough Derby points, maybe his pony just prefers long rests.

But like I said, I scare easily. Will use only if Churchill is underwater.

5. Tapit Trice (99)

Trainer: Todd Pletcher

Last race: Blue Grass Stakes (1st)

Odds: 9-2

One of my favorites. Of course, he is only trained by Todd Pletcher and his tentacle device. To my sweat, Tapit Tris is gradually getting much better – as you would expect whenever a horse comes under the guidance of a good trainer. Tapit-3 had just defeated my baby, Verifying, in a battle at Keeneland. But that was just a warm-up. The real battle will be on Sunday.

But Todd’s fortune still holds. Tapit Tris drew the 5yo, which is statistically the best placement after the Derby. Sometimes it costs me money, but I will bet again on one of the horses trained by Pletcher.

Here is the corrected version of the text with grammar and punctuation errors fixed:

6. Kingsbarns (95)

Trainer: John Pletcher

Previous race: Louisiana Derby (1st)

Odds: 10-1

Oh, guess what? The second most successful post position in the Derby is post 6. Pletcher and his guys follow us around like the plague. I just can’t shake them. The horses he trains are everywhere; sometimes I wish he would be caught doing something wrong. Then I would have a legitimate reason to dislike him.

But they won’t. Pletcher never does. He’s as direct and straightforward as they come. On paper, Kingsbarns is supposed to be Todd’s third horse after Tapit Thrice and the favorite, Weakness. I think differently. Kingsbarns might be his best horse.

7. Reincarnate (95)

Trainer: Harry Yakteen

Previous race: Illinois Derby (3rd)

Odds: 13-1

This is an easy throw out despite being ridden by top jock Johnny V. The convicted drug cheater, Bobby-Bob Baffert, had to transfer his Derby contenders to trainer Harry Yakteen to qualify them for the Derby while Bobby-Bob served his suspension.

Whatever these two trainers are doing, it’s not making the horses better. Reincarnate is going backward. His recent finish at Oaklawn was nothing to write home about, and he had no excuse. The race was right there in front of him. But his vision also included the winner, Angel of Empire, about 10 or more lengths ahead.

8. Mage (94)

Trainer: Jorge Flojo

Last race: Florida Derby (2nd)

Odds: 17-1

Got him in the Florida Derby, and he nearly pulled it off. Caught big favorite Strength at the top of the stretch but got caught in turn in the final hundred yards. Really. Nice effort by a gutsy horse. However, Mage might be his own worst enemy; he’s always slow out of the gate. What’s this guy doing in the race? Watching the butterflies? You can get away with slow starts in other races. Not in the Derby.

Maybe a simple fix, but then again, maybe not. I like this horse, so I’m not tossing him out just yet.

WATCH: These casinos and racetracks are hosting Kentucky Derby watch parties, events.

9. Skinner (98)

Trainer: Bob Shirreffs

Last race: Santa Anita Derby (3rd)

Odds: SCRATCHED

Note: Since publication of this article, Skinner was scratched from the Kentucky Derby due to fever. He will not be replaced as all replacements had already been used when he scratched.

Wasn’t supposed to be here but got in on a late scratch. Unlike some other previous late entries, this guy is actually good. Real good. Came up just short at Santa Anita and probably needed just another 25 yards of track to catch the winner, Useful Move.

Trainer Bob Shirreffs knows what he’s doing, I suppose. But with a colt this good, why did Kim rely on luck and a scratch to get into the top dance? Okay, maybe Skinner is a late bloomer, but late entries make me nervous, especially when I’m not betting on them.

Besides, who would name their million-dollar pony Skinner? Doesn’t sound like Secretariat, God forbid he wins the Triple Crown. Pass.

10. Practical Head (100)

Trainer: Tim Yakteen

Last race: Santa Anita Derby (1st)

Odds: SCRATCHED

Note: Since publication of this article, Practical Head was scratched from the Kentucky Derby due to fever. Cyclone Mischief (91) is the replacement.

Tim Yakteen has always been the primary trainer, not Baffert. So far, so good for Tim. But his guy started to fade at Santa Anita and got caught. That was nine furlongs, so will this pony want 10? It gives me pause; there is a big difference between nine furlongs and 10 furlongs.

His sire was Practical Joke. I still remember betting on him in the Derby not too many years ago. I believed in him big. I lost big. The practical joke was on me. Will pass on the Santa Anita winner, with pleasure.

11. Deactivate (90)

Trainer: Steve Asmussen

Last race: Lexington Stakes (3rd)

Odds: 25-1

This guy is trained by Steve “Needles” Asmussen, who was caught on tape administering things to his horses back when. After a long investigation, he was cleared, offering a defense of “show me the money.” In his case, “prove that it was illegal injections.” Needles claimed it was just vitamins.

Deactivate is going to need a COVID shot for this race. His best Beyer is 80, and he may be regressing. You don’t want to know what I really believe. Pass.

12. Jace’s Road (90)

Trainer: Anthony Cox

Last race: Louisiana Derby (3rd)

Odds: 32-1

Another Cox-trained horse. Made it to the Derby via a backdoor scratch. He won Gun Runner some time back and then ran poorly in two prep races in the slop, including the Southwest. I was willing to concede to trainer Cox that his pony doesn’t like dirt. But in his last race at Fairgrounds, he failed to fire when the opportunity was given to him. Cox can’t make everyone great. Staying away.

13. Sun Thunder (88)

Trainer: Ken McPeek

Last race: Blue Grass Stakes (4th)

Odds: 30-1

I wish he was faster. His best Beyer of 88 is just not enough. I love his style; he cruises, he waits, then near the finish, he accelerates. Sun Thunder is the classic closer. But on Saturday in the Derby, there will be a lot of horses to pass, which means a lot of work. If he was faster, maybe he could be closer to the leaders and positioned better to execute his closing magic. But he’s not. Must pass.

14. Angel Of Disposition (94)

Trainer: Brad Cox

Last race: Arkansas Derby (1st)

Odds: 9-2

This is my man. Bet him as the winning long shot in the Rebel Stakes (G2). Then Angel made the Arkansas Derby look like child’s play. That’s what good horses do; they get better when they’re handled by a good trainer. Best Beyer of 94 is only so-so, and the 12 post leaves something to be desired, but that’s okay.

Angel can show speed and has tactical speed. That means he will listen to his jockey and hold back a little until asked. Tactical speed means he can accelerate quickly and secure a position, then settle to cruise. Horses must conserve their energy for the end. However, some horses won’t do that.

Frank Springer, the real trainer of War Emblem, tried to teach him, but his pupil wouldn’t listen. Finally, he just gave up and let War Emblem be the “rabbit” he was always destined to be. Instructed his jockey to let him go and hold on. War Emblem won the Illinois Derby,

the Kentucky Derby, and the Preakness. Only foiled by the 10 furlongs at Belmont, rebuffs for rabbits.

Want another reason why I like post 13? Angel Of Disposition is right next to the favorite Practical Joke at post 15. If only I was a fly on the wall to hear the trainer/jockey pre-race strategy. Remember what I wrote about the race within the race — the short sprint to the first turn.

15. Stand Out Point (100)

Trainer: Todd Pletcher

Last race: Florida Derby (1st)

Odds: SCRATCHED

First, let’s get something right. I am a Francophile, and “forte” is a Latin word. The pronunciation of forte is with a silent e, fort. If it had an accent mark on the e, it would be pronounced “for-tay.” But there is no grammar signal. It’s pronounced “fort” no matter how many others get it wrong. When one borrows a word from another language, at least get the pronunciation right.

As far as the horse, I don’t bet favorites in a 20-pony pool. Pass.

16. Raise Cain (90)

Trainer: Bill I. Mott

Last race: Illinois Derby (4th)

Odds: 30-1

Gotham winner in the slop going away. He even beat a loose horse who threw his jockey at the gate. But Cain has shown little since. Ran two recent races two weeks apart with mediocre results. Two races that collectively have become unusual in these days of coddled favorite ponies.

I mention here that even the great Seabiscuit, until he found his foot, was running weekly. More races won’t help Cain. He’s not good enough. Pass.

17. Derma Sotogake (N/A)

Trainer: Hidetaka Otonashi

Last race: UAE Derby (1st)

Odds: 7-1

This Japanese-owned horse came out of Lebanon, another way to qualify for Louisville. People estimated his Beyer for the Dubai race was about 101. Right. Many horse players like him; otherwise, he wouldn’t be a 6-1 morning line. But I think otherwise.

The DRF tells us that Japanese shippers are 0-for-18 in the Kentucky Derby. And what’s worse, not even one o-fer has finished as high as fourth. Not one. I’ve been to Japan countless times. A decent place, I quite like it, spent Christmas Eve there once. Perhaps today’s Japanese ponies are seduced by the warm winter sunshine, the Duty-Free, maybe even the sake. I guess. But one thing I do know: I will not bet on Derma to break the long losing streak.

18. Rocket May (91)

Trainer: Bill I. Mott

Last race: Illinois Derby (4th)

Odds: 27-1

In 2019 Mott became a Derby winner when the charge, Country House, was declared the winner despite finishing well back of first at the line,

Maximum Security. However, Country House won when Maximum Security was disqualified for interference. (An unfair decision, though I admit Maximum Security was my pick.)

Anyway, Churchill Downs was under water that first Saturday in May and all the ponies were slipping and sliding around. But arguing with the stewards and race officials is like arguing with the girlfriend or the IRS, you will never win. Regardless, Mott and Rocket May won’t have to worry about things like that. This year his horse has no shot.

19. Lord Miles (93)

Trainer: Saffie Joseph Jr.

Last race: Wood Memorial (1st)

Odds: DAMAGED

Note: Since publication of this article, Lord Miles was scratched from the Kentucky Derby due to a suspension given to trainer Saffie Joseph Jr. King Russell (87) is the replacement.

Saffie, the trainer, left his lair in South Florida and brought his horse North, thus capturing the Wood Memorial. Good for him. The Grade 1 Wood, unfortunately, is not as prestigious as it used to be. Harkening back to when the connections for Secretariat put the great one in the race and where he suffered his only defeat.

Lord Miles had and ran a perfect race, no obstacles and no stress. But still only received a 93 Beyer. Lord is not fast enough. Will pass.

20. Continuar (N/A)

Trainer: Yoshito Yahagi

Last race: UAE Derby (3rd)

Odds: DAMAGED

Note: Since publication of this article, Continuar has been scratched from the Kentucky Derby due to a decision from trainer Yoshito Yahagi. Mandarin Hero (100) is the replacement.

This horse qualified through Japan Road where the guaranteed spot goes to the horse with the most points in a five-race series. The Japanese make great torpedoes, fighter planes, and cars but have not produced many decent Derby horses.

Continuar has yet to win this year, and the April Cherry Blossoms in Washington, D.C., have long since seen their flowers fade.

How did this horse get here? I think I know. Carry boards, thankfully, cannot show beyond 99-1, and if I had a horse that somehow qualified for the Kentucky Derby, I know what I would do: “Look out guys and save some of the bourbon, I’m coming!”

21. Cyclone Mischief (91)

Trainer: Dale Romans

Last race: Florida Derby (3rd)

Odds: 32-1

Cyclone Mischief got his start at Churchill Downs, debuting in September. But all four of his races as a 4-year-old came at Gulfstream Park in Florida. He finished third in the Florida Derby on April 1 and was three lengths behind Essential Quality.

He may be close to the front of the pack at the start, but don’t expect that to last in the home stretch.

22. Mandarin Hero (100)

Trainer: Terunobu Fujita

Last race: Santa Anita Derby (2nd)

Odds: 21-1

Mandarin Hero is a late entry due to a scratch, but he’s got a legitimate shot to make some noise. That 100 Beyer Speed Figure is eye-opening and solid, and he’s one of the four Japanese-bred horses who are either in the field or were in contention (Continuar and Derma Sotogake are the other two) who have previously competed in the US.

However… let’s not forget that 0-for-19 record of Japanese-bred horses in the Run for the Roses?

23. King Russell (87)

Trainer: Ron Moquett

Last race: Arkansas Derby (2nd)

Odds: 32-1

King Russell is a fast-rising horse that needed five races to break his maiden, breaking through on Feb. 25 at Oaklawn. Just three weeks after that, he finished second in the prestigious Arkansas Derby. And now? He’s in the Kentucky Derby.

That Beyer Speed Figure is the slowest in the field, so I wouldn’t ride with this longshot pick today.

Is another Kentucky Derby upset imminent?

Despite all our great prognosticators, horse racing can be beset by inexplicable surprises or mishaps.

Take last year for example; Authentic was sitting at 21 and out of the race until D. Wayne Lukas scratched his pony later. Then suddenly Authentic was in, from post 15. Then Authentic went out and won. How he did it still amazes me. On paper, he was nothing, coming out of post 20, the task seemed impossible, but he won and paid 80-1. How can you not love horse racing?

My 2023 Kentucky Derby picks

My bets this year will be:

$50 to win on 14, Angel Of Disposition

$20 to place on 14, Angel Of Disposition

$20 win-place on 2, Essential Quality

$20 win-place on 6, Kingsbarns

I like the next longshots and will do $12 win-place bets on:

13, Sun Thunder, at 50-1

12, Jace’s Path, at 50-1

19, King Russell, at 30-1

Please note: Since publication of this article, King Russell was scratched from the Kentucky

Derby due to a suspension given to trainer Saffie Joseph Jr. No replacement was made.

My brother-in-law Gordon likes to play $1 dollar tri-boxes. Pick any three horses in any order. It’s only $6, and I may play around with it based on my picks above. But remember, for the tri-box to pay anything, you need to include a longshot.