I’m Making These 7 Bets, Longshot Picks For The 2023 Kentucky Derby

Written By Jack Flaherty on May 4, 2023 - Last Updated on May 6, 2023
My best bets, longshot picks for Kentucky Derby 2023, from playma.com

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

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

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

Normally, 20 horses run. This year, we’ll have just 18 horses racing. There were five scratches and the full allotment of three replacements used.

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

Note: Since publication, Practical Move, Skinner, Lord Miles, Forte and Continuar all scratched for varying reasons. There were only three replacement horses — Mandarin Hero, Cyclone Mischief and King Russell — so 18 horses will run.

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Kentucky Derby 2023 horses and trainers

1. Hit Show (93)

Trainer: Brad Cox

Last race: Wood Memorial (2nd)

Odds: 26-1

Unless your pony is a rabbit who likes to get out front early, the 1-post buries horses. The last Derby winner from 1 was Ferdinand in 1986. There are two races in the Derby — the finish and the race to the first turn. Once there, you hope your pony is in good position and can settle down and run as close to the rail as possible, taking the shortest way possible around the oval.

Not sure Hit Show can do that. His best two efforts this year were at Aqueduct, but I doubt the Churchill people plan to move the race there this week. A Cox-trained colt but I must stay away.

ALSO READ: Kentucky Derby Basic Betting Tips For Beginners

2. Verifying (99)

Trainer: Brad Cox

Last race: Blue Grass Stakes (2nd)

Odds: 17-1

More bad news for Cox: The 2-post is not much better than 1. There used to be a time when the outside posts were considered death, but no longer. We have had several recent winners from outside, including Rich Strike last year from 20, Big Brown from 20 in 2008 and CountryHouse at 18 in 2019, plus others.

Today, I would take post-19 over post-2. But that won’t take me off Verifying. I have liked him all year. He finished a rapidly closing fourth in the slop at the Rebel, even after suffering a nightmare trip. But Verifying never quit. The Keeneland fans were treated to a dramatic stretch drive recently between Verifying and Tapit Trice in the Blue Grass Stakes.

Verifying was a close second but Cox now has had four more weeks to train him up. This colt has heart and I am betting him somewhere on my FanDuel Racing Massachusetts app.

3. Two Phil’s (101)

Trainer: Larry Rivelli

Last race: Jeff Ruby (1st)

Odds: 7-1

From habit, I usually discount races and figures run on a synthetic surface such as the new Tapeta artificial surface at Turfway. But this prejudice also encouraged me to neglect Derby winners such as Animal Kingdom in 2011 and Lil E Tee in 1992. Not to mention Preakness winners Summer Squall and Prairie Bayou.

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

4. 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 a long time ago. I wonder why Desormeaux did not give him another race. I scare easily when it comes to the Derby. Especially when I think a horse is being held back. 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 under water. 

5. Tapit Trice (99)

Trainer: Todd Pletcher

Last race: Blue Grass Stakes (1st)

Odds: 9-2

One of the favorites. Of course, he is trained by Todd Pletcher and his tentacled  machine. To my discomfiture, Tapit Trice has been getting progressively better — as one would expect when a horse is placed under the management of a good trainer. Tapit-3 just beat my boy, Verifying, in a battle at Keeneland. But that was only a warm-up. The real thing is Saturday.

But Todd’s luck is still holding. Tapit Trice drew post 5, which is the best Derby post position according to stats. It costs me money sometimes, but I will again pass on a Pletcher-trained horse.

RELATED: Kentucky Derby Still Major Gambling Event In MA, Even With Legal Sportsbooks

6. Kingsbarns (95)

Trainer: Todd Pletcher

Last race: Louisiana Derby (1st)

Odds: 10-1

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

But they won’t. Pletcher never will. He’s as straight and honest as they come. On paper, Kingsbarns is supposed to be Todd’s third horse after Tapit Thrice and the favorite, Forte. I think otherwise. Kingsbarns is his best horse.

7. Reincarnate (95)

Trainer: Tim Yakteen

Last race: Arkansas 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 turn over his Derby contenders to trainer Tim Yakteen, to qualify them for the Derby while Bobby-Bob served his suspension.

Whatever these two trainers are doing, it’s not making the horse better. Reincarnate is going backwards. 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 away.

8. Mage (94)

Trainer: Jorge Delgado

Last race: Florida Derby (2nd)

Odds: 17-1

Had him in the Florida Derby and he almost pulled it off. Caught big-favorite Forte at the top of the stretch but got caught-in-turn the final 100 yards. Damn. Nice effort by a gutsy pony. But Mage could be his own worst enemy; he is always slow out of the gate. What’s this guy doing in the cage? Looking at butterflies? You can get away with slow starts in other races. Not the Derby.

Maybe an easy fix, but maybe not. I like this pony, not throwing it out yet.

WATCH PARTIES: These MA Casinos And Racetracks Are Hosting Kentucky Derby Watch Parties, Events

9. Skinner (98)

Trainer: John Shirreffs

Last race: Santa Anita Derby (3rd)

Odds: SCRATCHED

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

Was not supposed to be here but got in on a late scratch. Unlike some other previous late entries, this guy is good. Real good. Came up just short at Santa Anita and probably needed only another 30 yards of track to catch the winner, Practical Move.

The trainer, John Shirreffs, knows what he is doing, most of the time. But with a colt this good, how did John rely on luck and a scratch to get into the big dance? OK, maybe Skinner is a late bloomer but late bloomers make me nervous, especially when I am not wagering on them.

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

10. Practical Move (100)

Trainer: Tim Yakteen

Last race: Santa Anita Derby (1st)

Odds: SCRATCHED

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

Tim Yakteen has always been his primary trainer, not Baffert. So far for Tim, so good. But his boy began to flatten at Santa Anita and almost got caught. That was 9 furlongs so will this pony want 10? It gives me pause; there is a big difference between 9 furlongs and 10 furlongs.

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

11. Disarm (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 maintained it was only vitamins.

Disarm is certainly going to need a COVID shot for this race. His best Beyer is 90 and he has been digressing. You don’t wanna know what I really think. Pass.

12. Jace’s Road (90)

Trainer: Brad Cox

Last race: Louisiana Derby (3rd)

Odds: 32-1

Another Cox-trained horse. Got into the Derby via a backdoor scratch. He won Gun Runner a while back and then ran poorly in two preps run in slop, including the Southwest. I was ready to concede to trainer Cox that his pony no likey mud. But in his last at Fairgrounds, he failed to fire when the chance 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 attacks. Sun Thunder is the classic closer. But Saturday in the Derby, there will be a lot of horses to pass and that means a lotta work. If he was faster, he could be closer to the leaders and positioned better to do his closing magic. But he’s not. Must pass.

14. Angel Of Empire (94)

Trainer: Brad Cox

Last race: Arkansas Derby (1st)

Odds: 9-2

This is my boy. Bet him as the winning long shot in the Risen Star (G2). Then Angel made the Arkansas Derby look like child’s play. That is what good horses do; they get better when they are managed by a good trainer. Best Beyer of 94 is only so-so and the 14 post leaves something to be desired, but that’s OK.

Angel can rate and has tactical speed. That means he will obey his jockey and hold back a little until asked. Tactical speed means he can speed up quickly and secure a better position, then settle back to cruise. Horses must reserve their strength for the end. However, some horses won’t do this. 

Frank Springer, the real trainer of War Emblem, tried to teach this but his pupil would not listen. Finally he just gave up and just let War Emblem be the “rabbit” he was always destined to be. Told 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 12 furlongs at Belmont, a brick wall for rabbits.

You want another reason why I like post 14?  Angel Of Empire is just inside the favorite Forte 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 inside the race — the sprint contest for the first turn.

15. Forte (100)

Trainer: Todd Pletcher

Last race: Florida Derby (1st)

Odds: SCRATCHED

Note: Since publication of this article, Forte was scratched from the Kentucky Derby due to a vet deeming him unfit to race Saturday morning. He will not be replaced, as all three replacements were already used when he scratched.

First, let’s get something straight. 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 above 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: William I. Mott

Last race: Arkansas 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. However, Cain has shown little since. Ran two recent races 14 days apart with mediocre results. Two races that close together have become rare in these days of coddled darling little ponies.

I mention here that even the great Seabiscuit, until he found his feet, 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 Dubai, another way to qualify for Louisville. People estimated his Beyer for the Dubai race was around 101. Huh. A lot of horse players like him, otherwise he would not be a 6-1 morning line. But I think otherwise.

The DRF informs that Dubai shippers are 0-for-18 in the Kentucky Derby. And what’s worse, not even one of those o-fers finished as high as fourth. Not one. I have been to Dubai countless times. A decent place, I kind of like it, spent Christmas Eve there once. Perhaps today’s Dubai ponies are seduced by the warm winter sunshine, the Duty-Free, maybe even the booze. I speculate. But one thing I do know: I will not wager on Derma to break the long losing streak.

18. Rocket Can (91)

Trainer: William I. Mott

Last race: Arkansas Derby (4th)

Odds: 27-1

In 2019 Mott became a first-time Derby winner when his charge, Country House, was declared the winner despite finishing well back behind first to the line, Maximum Security. Nevertheless, Country House won when Maximum Security was taken down for interference. (An atrocious decision, although I admit Maximum Security was my guy.)

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

19. Lord Miles (93)

Trainer: Saffie Joseph Jr.

Last race: Wood Memorial (1st)

Odds: SCRATCHED

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 shipped his horse North, thus capturing the Wood Memorial. Good for him. The Grade 1 Wood, unfortunately, is not as prestigious as it once was. Harkening back to when the connections for Secretariat put the great one in the race and where he suffered his only loss.

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

20. Continuar (N/A)

Trainer: Yoshito Yahagi

Last race: UAE Derby (3rd)

Odds: SCRATCHED

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

This horse qualified via Japan Road where a guaranteed spot is reserved for the pony with the most points in a five-race series. The Japanese have made great torpedoes, fighter planes and automobiles, but have not produced many decent Derby horses.

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

So why is this pony here? I think I know. Tote boards, thankfully, cannot demonstrate beyond 99-1 and if I had a horse that somehow qualified for the Kentucky Derby, I know exactly what I would do: “Look out guys and save some of the bourbon, I’m coming in!”

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 3-year-old came at Gulfstream Park in Florida. He finished third in the Florida Derby back on April 1 and was three lengths behind Forte.

He could be near the front of the pack in the beginning, but don’t expect that to last into the home stretch.

22. Mandarin Hero (100)

Trainer: Terunobu Fujita

Last race: Santa Anita Derby (2nd)

Odds: 21-1

Mandarin Hero is a late add due to a scratch, but he’s got a legitimate shot to make some noise. That 100 Beyer Speed Figure is eye-opening and legit, and he’s the only of the three Japanese-bred horses who are either in the field or were in the field (Continuar and Derma Sotogake are the other two) who has previous trained in the US.

But … remember that 0-for-19 stats about 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 five weeks after that, he finished second at the prestigious Arkansas Derby. 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 of us great prognosticators, horse racing is beset by inexplicable surprises or upsets.

Take last year for example; Rich Strike was sitting on 21 and out of the race until D. Wayne Lukas scratched his pony late. Then suddenly Rich Strike was in, at post 20. Then Strike 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 14, Angel Of Empire

$20 to place 14, Angel Of Empire

$20 win-place 2, Verifying

$20 win-place 6, Kingsbarns

I like the following longshots and will also do $10 win-places on:

13 Sun Thunder at 50-1

12 Jaces Road at 50-1

19 Lord Miles at 30-1

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.

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

Photo by AP Photo/Charlie Riedel
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Jack Flaherty

Jack Flaherty independently represented manufacturers in the Middle East and Africa for 29 years and is a lifelong horse racing fan who, on two occasions, successfully bribed the National Guard with cheap beer and hopped the fence to attend the 1974 and 1975 Kentucky Derby. Jack currently resides in Falmouth, Massachusetts.

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