2021 Kentucky Derby Analysis and Betting Tips by a Lawyer with a Lifelong Horse Habit

By: Amanda Simmons Luby

TV Coverage: NBCSN 12:30pm-2:30pm; NBC 2:30pm-7:30pm. Post Time: 6:57pm EDT. Location: Churchill Downs, Louisville, Kentucky. Age: only three-year-olds. Distance: 1 ? miles (10 furlongs)(a furlong is one-eighth of a mile)

Post Position Horse (Pedigree). Morning Line Odds

1. Known Agenda (Curlin – Byrama {GB}, Byron {Ire}). 6/1. A relentless, come-from-behind grinder that really knows how to reach into his stride, this horse has been training lights out even though he’s not considered a great work horse. He does, however, know how to turn it on in the afternoons. Plus, he knows how to take a few bumps during the course of the race. This gorgeous chestnut won the Florida Derby in his last start and you can tell the longer the race is, the better. He’s maturing at the right time and seems very focused right now. Sired by two-time Horse of the Year, Curlin, Known Agenda is a true, classic dirt horse that should love the 1 ? distance. I hate the inside post for him since he’ll have to deftly weave through traffic to win, but given everything else, definitely consider him in your win wagers as well as all exotic wagers. I really like this horse to win. Jockey: Irad Ortiz, Jr. (last year’s champion jockey had many options and chose this horse). Trainer: Todd Pletcher (elected to Hall of Fame this year; won two Derbies). Breeder/Owner: St. Elias Stables (owned by Vinnie Viola, a West Point grad; won the Derby a few years ago in an ownership group with Always Dreaming). 

2. Like the King (Palace Malice – Like A Queen, Corinthian). 50/1. Purchased for $170,000 as two-year-old in training, Like A King won his Derby prep in convincing fashion even after experiencing some traffic trouble in the race. However, it was against lesser quality (including Sainthood) than what he’ll be facing in the Derby. He’s been training very well up to the race with a series of long, speedy drills. He’ll have the fitness to win and is trained by Wesley Ward who is a bit of a horse whisperer. This horse is a closer and will come from far back. His lack of early speed could be an impediment to winning, but as a closer, it’s hard to ignore him in your exotic wagers. Jockey: Drayden Van Dyke (talented, young jockey). Trainer: Wesley Ward (never won the Derby and typically specializes with speedier two-year-olds). Owner: M Racing Group LLC. Breeder: Horseshoe Racing LLC.

3. Brooklyn Strong (Wicked Strong – Riviera Chic, Medaglia d’Oro). 50/1. You could have bought this New York-bred for a mere $5,000 as a two-year-old at auction last year and now he’s in the Derby! Winner of a major two-year-old race late last year beating top contender Known Agenda, he hasn’t been as consistent this year and was most recently beaten soundly by Bourbonic and Dynamic One in their last race. In fact, Brooklyn Strong only was accepted into the field after three others defected from the race due to injury, illness or distance limitations. He’s been training decently at his home track in Pennsylvania, but we have no idea how he’ll handle the Churchill track. He’ll go off as a super longshot and I’m unlikely to put any money on him since getting into the Derby seemed more happenstance than anything, but when the horse is sound and training well, you can’t blame the team for wanting to run in the Derby. Fortunately, he also has an excellent jockey in the irons. Jockey: Umberto Rispoli (1st Derby; 2x champion Italian jockey that just came to the US in January; has been riding exceedingly well and actually rode Rock Your World in his last win). Trainer: Daniel Valazquez (never had a Derby starter). Owner: Mark Schwartz. Breeder: Cheryl Prudhomme & Dr. Michael Gallivan.

4. Keepmeinmind (Laoban – Inclination, Victory Gallop). 50/1. Winner of an important two-year-old race at Churchill Downs last Fall, Keepmeinmind tries hard every time. It should be noted that major stallion operation, Spendthrift Farm, was so impressed with Keepmeinmind last year that they purchased his breeding rights. However, he just hasn’t put it all together as a three-year-old and hasn’t hit the board this year in his two starts. Beaten by Essential Quality every time they’ve met, I don’t think he’s matured as well as others have into his three-year-old year. He’s bred to get the distance and typically comes from well off the pace, so he may gallop on strongly enough to finish third or fourth (if the pace is fast enough), but I would really be surprised if he did better than that. Blinkers off for the Derby which should make him keener. Jockey: David Cowen (1st Derby start). Trainer: Robertino Diodoro (1st Derby start). Owner: Cypress Creek Equine, Arnold Bennewith, and Spendthrift Farm LLC. Breeder: Southern Equine Stables LLC

5. Sainthood (Mshawish – Lemon Hero, Lemon Drop Kid). 50/1. With a pedigree laced with stamina influences, getting the Derby distance should be no trouble for this up-and-coming horse. Todd Pletcher has this horse firing on all cylinders. Second to Like The King in his final prep for the Derby after experiencing a lot of traffic trouble, he’s training fabulously and with enthusiasm over the track. This is your Hail Mary bomb. The least heralded of Pletcher’s four entrants, Sainthood was purchased by his connections for just $62,000; but his connections won the Triple Crown with Justify and are heavyweights in the industry. This horse is an athlete, by a young unproven stallion, and would be a surprising, but interesting choice to win. Jockey: Corey Lanerie (Churchill is his home track; never won the Derby). Trainer: Todd Pletcher. Owner: Winstar Farm LLC & China Horse Club. Breeder: Edward Taylor & Springland Farm

6. O Besos (Orb – Snuggs and Kisses, Soto). 20/1. A lot of racetrackers like how this horse is maturing. He’s never won a stakes race, though he finished well in his last prep, the Louisiana Derby, in which he finished third after having a clean run from the back of the short and closely-boxed field. However, I’m just not convinced he’s capable of beating the top four or five horses unless he gets a dream trip. His sire won the Derby so distance should not be a problem and, like with Hot Rod Charlie, Midnight Bourbon, and Mandaloun, he’s one of just a few horses that have run 1 3/16 miles in their last race (just a sixteenth of a mile shorter than the Derby distance). He’ll be fit, but whether he’s fast enough is a different story. He’ll pay a good price so don’t be afraid of using him in your exotic wagers. He’ll come from way back. Name translates to “O Kisses” in Spanish. Jockey: Marcelino Pedroza. Trainer: Gregory D. Foley. Owner: Bernard Racing LLC, Tagg Team Racing and West Point Thoroughbreds. Breeder: L. Barrett Bernard.

7. Mandaloun (Into Mischief – Brooch, Empire Maker). 15/1. Mandaloun trains like he is sitting on a big performance, with two “bullet” works in his last two major breezes[1] for the Derby. He floats over the Churchill surface and seems to beg for more work. He is certainly frisky and full of himself. You want to see that kind of confidence going into a big race. He failed to fire in his last race, the Louisiana Derby, where Hot Rod Charlie and Midnight Bourbon soundly beat him, but in the race prior, it raced very professionally and beat Midnight Bourbon. No one can figure out why he threw such a dud in his last race, but feel free to throw that race out. Bred to be a champion (and blue-blooded as they come), this horse is very live so you have to consider him in your wagers. Jockey: Florent Geroux. Trainer: Brad Cox (Louisville native). Owner/Breeder: Juddmonte Farms, Inc. (estate of HRH Khalid Abdullah).

8. Medina Spirit (Protonico – Mongolian Changa, Brilliant Speed). 15/1. You could have purchased this Florida-bred Derby starter for a mere $1,000 when he was a weanling or just $35,000 when he was a yearling. Regardless, as an earner of over $315,000, this blue-collar horse managed to find his way into the barn of two-time Triple Crown winning trainer Bob Baffert. A hard-trying horse that’s never finished worse than second, I cannot see this horse winning as the distances lengthen. He has a lot of stamina-oriented bloodlines in his second and third generations and is very hard to pass in distances up to 1 1/16 miles. However, he’s built more like a sprinter/miler and I just think the Derby distance will be too far for him. A horse that likes to sit close to the lead, he was easily beaten by Rock Your World in their last race. Jockey: John Valazquez (Hall of Fame; 3x winner of the Derby). Trainer: Bob Baffert (Hall of Fame; 6 Derby wins, tied for all time # 1). Owner: Zedan Racing Stables, Inc. (owned by Saudi Arabian businessman and philanthropist, Amr. F. Zedan). Breeder: Gail Rice.

9. Hot Rod Charlie (Oxbow – Indian Miss, Indian Charlie). 8/1. Winner of the 1 3/16 miles Louisiana Derby in his last prep for the Derby where he was able to set moderate fractions and lead start to finish, Hot Rod Charlie has been training off the charts these past few months. He is a “wise guy” horse and his owners are some of the most down-to-earth folks in the game. Plus, this horse is versatile regardless of pace (meaning, he could set the pace or come from off it). Even though he has a more modest pedigree than some of the others and was purchased for only $17,000 (and matured into a $110,000 2YO), he is bred to get the distance and is trained by Doug O’Neill who has won the Derby twice and nearly captured the Triple Crown a few years ago. He’s lost to other Derby hopefuls, Essential Quality and Medina Spirit. Yet, as we know with young athletes, they blossom at different times so while Medina Spirit may have been better a few months ago, Hot Rod Charlie may have passed him at this point particularly as the distances have increased. I can’t see him winning, but wouldn’t be surprised if he places. Feel good story: he’s running for a cause, to help fund the Jake Panus Memorial Scholarship at the University of South Carolina, named in honor of a 16-year-old boy who was tragically killed last summer. Post position 9 also is apparently a lucky number for the connections, too, so definitely put some money on him. Jockey: Flavian Prat. Trainer: Doug O’Neill. Owner: Roadrunner Racing, Boat Racing LLC and William Strauss (founder of ProFlowers.com). Breeder: Edward Cox, Jr.

10. Midnight Bourbon (Tiznow – Catch the Moon, Malibu Moon). 20/1. A cheeky racehorse that got loose from his handlers last week, cantering freely between barns while petrifying his connections who spent $525,000 to buy him as a yearling, this classically bred horse just seems like a big kid. A gorgeous dark bay horse with a blaze, he is always in the money and is bred to get the distance, but he just seems like he’s not applying himself fully and he has a tendency to act goofy. Beaten two lengths by Hot Rod Charlie in their last prep race, Midnight Bourbon is that frustrating horse that you just wish would put his mental and physical game together. He’s been training very well up to the Derby and he’s back at Churchill Downs, which is his home track. Typically on or near the lead early in his races, this horse may sneak in and get a big piece of the pie so don’t rule him out particularly since this race may set up for horses that race on or near the lead. He has the talent and will pay a good price. This position should help his cause. I just hope he doesn’t have a melt-down in the paddock when he’s being saddled because he's been acting nutty in his paddock training sessions this week. Jockey: Mike Smith (won Derby 2x; rode Justify to Triple Crown win in 2018). Trainer: Steve Asmussen (Hall of Fame). Owner: Winchell Thoroughbreds, LLC (think Winchell's donut chain). Breeder: Stonestreet Thoroughbred Holdings, LLC (which also bred three of the leading contenders for this years KY Oaks).

11. Dynamic One (Union Rags – Beat The Drum, Smart Strike). 20/1. A $725,000 yearling, Dynamic One just barely lost to his stablemate, Bourbonic, in their last prep race. Dynamic One had the lead until the very last jump and had been looking around (which caused him to shorten his stride) when he was caught at the wire from a horse he likely didn’t even see coming. A horse that does well with the distance and can perform well even if his trip is troubled, Dynamic One is maturing at the right time and has been training very well over the Churchill surface. A long-striding horse, he actually is quite adept out of the gate and has enough speed where he can position himself coming out of the crowded gate. His Hall of Fame trainer has tinkered with his blinkers during the past few weeks in an effort to get him to focus better. I will definitely be putting a few dollars on this horse. He's a live longshot. Jockey: Jose Ortiz (champion jockey; has placed in Derby, but never won). Trainer: Todd Pletcher (2x Derby winner; Hall of Fame). Owner: Phipps Stables, St. Elias Stables, Inc., Repole Stable (a powerhouse partnership of exceedingly wealthy owners). Breeder: Phipps Stables (sold the horse and then stayed in for a piece)

12. Helium (Ironicus – Thundering Emilia, Thunder Gulch). 50/1. A talented, undefeated horse (but with only three starts total) that has ample stamina in his pedigree, this horse hasn’t raced since he won his only prep for this race in early March. From a fitness perspective, that could be a major drawback. Plus, in looking at his works, he’s not been training impressively over the Churchill Downs surface. While trainer Mark Casse is a phenomenal trainer who can get horses fit off long lay-offs, this just seems too big of a stretch given how crowded the Derby field is. Purchased as a yearling for just $55,000 and bred off a $5,000 stud fee, a win by this big, strong colt would be a surprise, but welcomed by all of the small breeders and owners out there. Jockey: Julien Leparoux. Trainer: Mark Casse (Canadian Hall of Fame). Owner: D.J. Stable, LLC (founder of Blue Buffalo natural pet foods). Breeder: Teneri Farm Inc. & Bernardo Alvarez Calderon.

13. Hidden Stash (Constitution – Making Mark Money, Smart Strike). 50/1. A $50,000 yearling, Hidden Stash placed in two of his three prep races for the Derby, but has never finished first in a stakes race. While the distance should not be a problem, I respectfully think this horse is in over his head. He ran a distant fourth to Essential Quality and Highly Motivated in their last race. With that said, he has been training well at nearby Keeneland racetrack and is coming in under the radar. He’ll pay a price if you want to keep him in your exotic wagers. This would be a longshot bomb of a play. Jockey: Rafael Bejarano. Trainer: Victoria Oliver (would be 1st female trainer to win Derby). Owner: BBN II Racing, LLC (a partnership founded by two longtime friends from Saratoga Springs). Breeder: Rhineshire Farm LLC.

14. Essential Quality (Tapit – Delightful Quality, Elusive Quality). 2/1  Undefeated and last year’s champion two-year-old, this exceedingly professional and blue-blooded racehorse knows where the wire is and knows how to fight, having to really dig down deep in his last prep to defeat the rapidly improving Highly Motivated. He is tactical and versatile, can lead or sit off the pace, and can win off slow or fast paces. His agility and good mind are some of his best assets. He is a deserving morning line favorite that is not afraid of a fight. Bred & owned by my former employer, Sheikh Mohammed bin Rashid al Maktoum (ruling minister of Dubai), Essential Quality, a steel gray colt, is bred to get the distance and is as competitive as they come. The question, though, will be whether the dogfight that he won in his last race took too much out of him. Horses either improve or “bounce” after such tough races. He’s looking very well coming into the race, and thus a deserving favorite, but we still have an opening for another horse to win. Also, note that philanthropist “Mattress Mac” of Houston, Texas will be placing a $2M bet on this horse as part of a promotion for his stores…so that will drive his odds even lower (largest single Kentucky Derby bet in history). Jockey: Luis Saez (who is on fire right now). Trainer: Brad Cox (2020 champion trainer; has never won the Derby, but he’s young yet). Breeder: Godolphin LLC (nom de course for the Sheikh). Owner: Godolphin LLC (has never won the Derby).

15. Rock Your World (Candy Stripes – Charm The Maker, Empire Maker). 5/1. A $650,000 yearling, this striking dark bay galloper is undefeated, versatile, and really maturing into himself at the right time. Quick out of the gate, he may take the lead or sit just off the frontrunner. Compelling is that he can sustain his speed – true speed – over a route of ground as he did in his final prep race, the Santa Anita Derby, where he literally ran his competition off their feet (which included Medina Spirit). It was the most impressive prep race of all of them where even after setting very fast fractions, he was able to lengthen his lead in the stretch and still finish his final sixteenth in a solid :12.90 seconds. With so many stalkers and closers in this race, Rock Your World’s speed creates a necessary “single” in your bets. He may win every pole. However, even if he doesn’t get to the lead immediately, he’s tactical enough to sit just off the pace and go by leaders in the stretch. He’s trained by one of the coolest heads in the business and will be fit and ready on the first Saturday in May. Jockey: Joel Rosario Jr. Trainer: John Sadler (a former show jumper). Owner: Hronis Racng LLC (two brothers who are lifelong racing fans), David Michael Talla, and David Ingordo. Breeder: 88-y-o Ron McAnally (Hall of Fame trainer who still trains a few horses at age 88) & Deborah McAnally.

16. King Fury (Curlin – Taris, Flatter). 20/1. A $950,000 yearling, King Fury is light on experience, but is training like a beast. Winner of his only race this year, the Lexington Stakes-G3 just three weeks ago, King Fury’s confidence is at an all-time high, but he was soundly beaten by Essential Quality, Keepmeinmind, and Hot Rod Charlie when they faced each other last year. Now, a lot can happen between last Fall and the Spring. Many colts can mature significantly during that timeframe. However, King Fury only got into the Derby because of a defection of a higher ranked horse, so that is something to consider. Nevertheless, given how well this horse has taken to the Churchill surface, that his pedigree just screams “1 ? miles,” and that his last speed figure puts him close to the top in terms of quality, it’s hard to ignore him. I expect him to make a good showing on Derby Day so consider him for your place and show bets. He’ll go off at a good price and is a closer. Named after boxer Tyson Fury. Jockey: Brian Hernandez Jr. (one of the nicest guys in the business). Trainer: Ken McPeek (hasn’t won Derby yet, but has won the other two jewels of the Triple Crown). Owner: Fern Circle Stables and Three Chimneys Farm LLC. Breeder: Heider Family Stables LLC.

17. Highly Motivated (Into Mischief – Strong Incentive, Warrior’s Reward). 10/1. By the same sire as last year’s Derby winner, this horse ran a very game second to champion and Derby favorite, Essential Quality, in their last race where they both ran high speed figures and battled down the entire length of the stretch. However, even though he still had everything his own way in their last race, the champ still got by him. In only two starts this year, he has yet to win, but he always shows up. Trainer Chad Brown has never won the Derby, but he knows how to get a racehorse fit and ready for such a big race. He has the speed figures to be a contender, but I’m not sure he actually wants to the mile and quarter distance. Jockey: Javiar Castellano (originally from Venezuela; Hall of Fame). Trainer: Chad Brown (4x champion trainer; 2d in the Derby in 2018). Owner/Breeder: Klaravich Stables, Inc. (nom de course of hedge fund manager, Seth Klarman).

18. Super Stock (Dialed In – Super Girlie, Closing Argument). 30/1. While he won his last prep race, the Arkansas Derby, in solid fashion, he’s not considered as good as the other horses that won their last preps. He’s the Roger Dangerfield in this race. This is a horse that anyone would love to have in his/her barn, but a win by him would surprise. This is the type of horse that would clean up in smaller derbies around the US at less competitive tracks and still earn lots of money, but I don’t see him going down in the history books. With that said, don’t be afraid of singling him in some show bets because he does try hard each time. Super Stock was a $70,000 yearling and is co-owned by the trainer’s father. It’s a heartwarming family affair and a win would be a “fate deal,” as Keith says, because they were supposed to sell Super Stock at a 2YO-in-Training auction last year, but the pandemic interfered with that…and now they’re in the Derby. Jockey: Ricardo Santana, Jr. Trainer: Steve Asmussen (Hall of Fame trainer; placed 4x in the Derby). Owner: Keith Asmussen (Steve’s father and a helluva horseman) and Erv Woolsey (producer for country superstars, George Strait & Lee Ann Womack). Breeder: Pedro Gonzalez & P. J. Gonzalez.

19. Soup and Sandwich (Into Mischief – Souper Scoop, Tapit). 30/1. Impeccably-bred and owned by a fabulous, Florida-based operation, this royal horse was, alas, given a silly name. I’m sorry (really, I feel bad about this); I just cannot cheer for a horse named after a lunch combo. In case you didn’t know, Live Oak Plantation, which bred and owns this horse, is owned by an heiress to the Campbell Soup fortune, hence the name. With only three starts underneath him, he’s light on seasoning and reportedly acts like a class clown. However, he ran a game second to Known Agenda in their final prep, the Florida Derby, and he is one of the few horses in this race than breaks quickly and can go to the front. Being toward the outside of the gate, though, he will need to break sharply if he hopes to be in the first flight of horses approaching the first turn. This horse is improving and will be easy to spot as he’s almost white. Noteworthy, however, is that Hall of Fame jockey John Valazquez chose to ride Baffert’s horse, Medina Spirit, rather than Soup and Sandwich. Jockey: Tyler Gafflione. Trainer: Mark Casse. Owner/Breeder: Live Oak Plantation, Inc.

20. Bourbonic (Bernardini – Dancing Afleet, Afleet Alex). 30/1. With a pedigree rich in Classic winners and owned/bred by the historic Calumet Farm, Bourbonic nevertheless surprised more than a few people (at 72-1) by winning his prep race, the Wood Memorial, by closing relentlessly in the stretch to just nose out his stablemate, Dynamic One, who got caught looking around in the stretch. Bourbonic will also race with blinkers which help keep him focused, but a large crowd on Derby Day could distract him. This closer will be hurt if any horse is allowed to set an easy pace on the front end (meaning the speed wouldn’t collapse, but hang tough). While a good horse and the outside post position should not impact his racing style, I think there are more agile plays. Jockey: Kendrick Camouche (1st Derby mount; from Louisiana). Trainer: Todd Pletcher. Owner/Breeder: Calumet Farm

SIMMONS SELECTIONS:  I’m going to ‘single’ Rock Your World for the win and box two exactas/trifectas with Known Agenda and Hot Rod Charlie. Additionally, I may include those horses in some exotic wagers (trifectas and superfectas) with Dynamic One, Hot Rod Charlie, Essential Quality, Mandaloun, and King Fury. Hail Mary bomb: Sainthood.

About the author: Amanda S. Luby breeds Thoroughbred racehorses and is General Counsel to CaptiveOne Advisors, LLC, a national captive insurance management company. Prior to becoming an attorney, Amanda groomed for Hall of Fame trainer, D. Wayne Lukas, broke yearlings for Sheikh Mohammed of Dubai, and was Director of Communications for Walmac International Stud Farm when it stood 20 stallions. She and her husband, Tim, split their time between Central Florida & Saratoga Springs, New York.   

[1] A breeze is a morning workout where a trainer seeks to really tighten the screws on a horse’s fitness and speed.  

Giddyup.