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Kentucky Derby 2021: Predictions, Picks, Contenders and Odds

Kentucky Derby 2021: Predictions, Picks, Contenders and Odds

Kentucky Derby 2021: Predictions, Picks, Contenders and Odds

The 2021 Kentucky Derby Preview comes with a little more normalcy this year than last year, starting with the fact that it's back in its traditional spot on the calendar compared to the 2020 edition, which took place in September.

If you want more detail on all 20 horses in this field, feel free to reach out to me on Twitter (@MarkStrausberg). But did you really want to read about each and every one of them? With four 50-1 shots and another four 30-1, you have at least half a dozen horses that are going to be complete non-factors.

However, I am going to answer a few questions and hopefully help you to earn a little moolah on Saturday.

Grab your mint julep, settle in, and we'll try to answer all your questions as we get into the starting gate. And they're off!

2021 Kentucky Derby Preview and Picks

Q: The odds are bound to change between now and post time, but what were the opening odds?

A: I'm glad you asked.

2021 Kentucky Derby contenders, odds



Essential Quality


Hot Rod Charlie


Medina Spirit


Rock Your World


Known Agenda


Highly Motivated




Midnight Bourbon


Super Stock




Caddo River


Dynamic One


Soup and Sandwich




Hidden Stash


Like the King




Q: Let's start at the bottom. Are there any long shots you like?

A: Well I definitely like a Soup and Sandwich, but that's because I'm a big fan of soup and a sandwich! If your horse's name contains food, good chance I'll bet on it in some fashion.

But of all the 30-1s, I like Dynamic One the best. Like a minor-leaguer that gets better at each stop, he definitely has an upward trajectory. Trainer Todd Pletcher has described his horse as one that is "still putting it all together." I'm not seeing him as a winner, but he's got plenty of stamina and recently finished second at the Wood Memorial. He's not a bad bet to include at the bottom of your trifectas and superfectas.

I also will be including Midnight Bourbon in a bet or two. That's because he'll be ridden by "Big Money" Mike Smith. Smith is one of the oldest jockeys to ever race in the Kentucky Derby and if he does win, he will be the oldest to do so. He has won more than 5,600 races including seven total Triple Crown series races. That's in addition to his record 26 Breeder's Cup races. One reason to like Smith and Midnight Bourbon is that's he had success with long shots at the Kentucky Derby before. He rode 30-1 shot Giacomo to win the roses in 2005 and this might be an even more impressive horse.

Q: Last year you liked favorite Tiz the Law to win. Will you be going with the favorite again this year?

A: Simply put, no. There's unquestionably a lot to like about Essential Quality. He was the champion two-year-old of 2020, finishing off the season by winning the Breeders' Cup Juvenile. He continued his success in 2021 by winning the graded Southwest at Oaklawn Park in his three-year-old debut. He then won another graded race, the Blue Grass at Keeneland.

However, I can't shake this gut feeling that he is peaking too early. Like a baseball team playing its best ball in June or a football team looking unstoppable in early November (see 2020 Pittsburgh Steelers), I think we've seen the best from Essential Quality. There is much better value further down the board.

Q: Any other popular choices you don't like this Saturday?

A: "Don't like" is a little strong, but yes, there are a few horses I like less that seem to be gaining momentum. The first one that comes to mind is Hot Rod Charlie. His trainer Doug O'Neill already has two Kentucky Derby wins under his belt (I'll Have Another in 2012 and Nyquist in 2016). Bettors are also loving that he won the Louisiana Derby and with a 99 Beyer Speed figure, one of the best performances. He also will be well-rested, coming off a 42-day break. Lest we forget, Authentic won the Derby last year off a 49-day break.

However, that was just one of the many ways that 2020 was a strange year and it was Authentic's fifth race that year since it was run in September. The last horse to win the Derby off such an extended break was Animal Kingdom 10 years ago. And before that, we go all the way back to before American Bandstand even premiered when Needles won in 1956. It's not an exact science, but there's a perfect window of rest for a thoroughbred. And this feels just a little too long for my tastes.

Q: Hmmm. Guess the 99 Beyer Speed figure doesn't do enough for you, does it? Although you did say "one of the best performances." What, did a horse hit 100?

A: You caught that, huh? And yup, Rock Your World hit 100 in his Santa Anita Derby win on April 2. He's the only horse in this field who has hit that mark. I keep waffling on whether or not to bet on him. I just can't recommend him though this far out. The weather forecast keeps changing. And if Churchill Downs is a muddy or sloppy track, few horses will be hurt more by those conditions than Rock Your World. I want to know track conditions before I make my final Derby bets.

Q: That leaves us with Bob Baffert's entry, Medina Spirit. I guess given Baffert's track record at the Derby, it's an easy choice.

A: No question about it, Baffert has a phenomenal record at the Derby. He won here last year with Authentic. That tied him for the most Kentucky Derby wins by a trainer and a win this weekend would give a record seven Derby winners! That's pretty gosh darn good.

And I know this sounds stupid, but something about Medina Spirit's competitive spirit doesn't sit right with me. Rock Your World finished ahead of him in the Santa Anita by over four lengths. He was a distant second to stablemate Life is Good in the San Felipe. Life is Good is a spectacular horse that would probably have given Baffert his seventh victory, but had minor surgery and will have to miss Triple Crown season. I think Medina Spirit can run a good race, but I just don't like him as a winner.

Q: Really? I guess that makes Known Agenda your choice to win? Or are you going to dip down even further for your winner?

A: Known Agenda is literally a "horse for the course" as his running style is the perfect match for the Kentucky Derby. Coming off a win at the Florida Derby at Gulfstream Park, he's finally showing his meddle. I just wish he had drawn a better post position. He drew the rail, and it has been nearly 35 years since a horse won the Derby from the rail when Ferdinand did it in 1986. but there is this:

Meanwhile, Midnight Bourbon has already dropped to 20-1, leaving us with two interesting choices in Highly Motivated or Mandaloun to win, both of which are aggressive picks. Mandaloun certainly has the higher ceiling, but the much lower floor as well.

It will be six weeks between the Kentucky Derby and the Louisiana Derby, Mandaloun's last race. Even more concerning however is Mandaloun's sixth-place finish in that race. Nine of the last 10 Kentucky Derby winners won their final prep. Mandaloun's trainer and Louisville native Brad Cox is still not sure what happened in the Gulf state, but many are marking it up to just "one of those days."

Yet Mandaloun was an early-season favorite. He has one of the best pedigrees in the field. Mandaloun comes from mare Brooch, making him the grandsire of Empire Maker. And he has seemed to rebound in his early workouts. That includes a duo of bullet-like workouts at Churchill Downs, zipping six furlongs in 1:11.40 on April 17 and five furlongs in 0:58.80 on April 10. He put in his final work on April 28, going five furlongs in 1:00 under jockey Florent Geroux before an additional furlong gallop-out in a sparkling 1:12.60. If you want value and are betting for the ceiling, take Mandaloun. Just be prepared to be either elated or disappointed.

Q: Should we make a pun about being Highly Motivated?

A: No, please don't. And I would actually be shocked if neither Mandaloun nor Highly Motivated are not part of the winning trifecta ticket. Both have seen their odds drop as people realize how open this race is. But even at 10 to 1, I still like the value that Highly Motivated brings to the table.

He does not have quite the pedigree of Mandaloun, but he is the grandsire of Harlans Holiday, who had nearly $4 million in winnings. Not too shabby. He also comes out Klaravich Stables, one of the winningest barns at Churchill Downs. I also love that in five career starts, he's never finished out of the money. Furthermore, he has been the one horse that has shown the ability to go toe-to-toe with not only Essential Quality, but also other highly-graded thoroughbreds.

Q: But what about Highly Motivated's jockey? Isn't that one of the top three or four factors you consider?

A: You readers can't see it, but I'm smiling. Highly Motivated's jockey is Javier Castellano. No, he has never won a Derby. It is similar to Ivan Lendl never winning at Wimbledon. Because Castellano has pretty much won everywhere else. He's a member of horse racing's exclusive 5,000-win club. Already inducted into the Hall of Fame, that honor came on the heels of four consecutive Eclipse Awards for being the nation's top jockey. He's won the Preakness. This year has not really had a feel-good sports story yet. You want to talk about highly motivated? Castellano overcomes his Waterloo and finally wins the Kentucky Derby.

Q: Solid. Last question: If I give you $20 to place a bet for me, what would it be?

A: It would be the following:

  • $1 Trifecta part wheel 17 WITH 1,7,11,15 WITH 1,7,11,15 for 12 $1 combinations or $12 total.
  • $1 Box Exacta WITH 14,8 for $2 total in case popular opinion is right.

And then I play six "lottery ticket" $1 Superfectas with 10, 11, 14, and 15. Obviously won't get all those combinations, but those are pure lottery tickets anyway, so I am not worrying about getting 'em all.

You've got my 2021 Kentucky Derby preview, now go win some money!

— Written by Mark Strausberg, a member of the Athlon Network Contributor, who despite his youthful exuberance and good looks has been playing fantasy sports before Wildcats or Hoosiers even made it to VHS. Got a fantasy sports question or thought? Hit him up on Twitter @MarkStrausberg.