One of the most sacred days on the sports betting calendar has arrived.
The 2021 Kentucky Derby will take place at 6:57 p.m. ET on Saturday, May 1 and will feature 19 horses running over the iconic main track at Churchill Downs in Louisville, Ky.
Essential Quality is the morning-line favorite after he drew the No. 14 post. The 2020 Breeders’ Cup Juvenile champion is a perfect 5-for-5 in his career under trainer Brad Cox, who is seeking his first Derby victory.
Our horse racing experts have detailed their favorite win bets and their favorite longshots for the Derby. They also included their favorite bet on the undercard, which is loaded with stakes races.
How you use these longshots (if at all) is up to you. Maybe you’re feeling froggy and want to put a few bucks on them to pull the upset — hey, we did see a 65-1 winner at Churchill in 2019 — or perhaps you want to go the safer route and play them underneath one of the favorites in your exactas and trifectas.
Let’s jump in:
Best Bet to Win the Kentucky Derby
No. 15 Rock Your World (5-1)
The Santa Anita Derby has proven to be one of the most successful prep races for the Kentucky Derby and last time out Rock Your World took the field gate-to-wire to win the Santa Anita Derby. He is 3-for-3, but the Santa Anita Derby was his first race on dirt.
Trainer John Sadler said that was the plan all along; start on the turf and then try the dirt, as the turf tends to be less taxing. Rock Your World is out of Candy Ride, whose offspring win at 21% in Grade 1 stakes races, which is unheard of, and the fact that Rock Your World has shown he can win in gate-to-wire fashion or that he can sit a stalking trip makes him a win contender and my top choice in this field.
No. 15 Rock Your World (5-1)
Initially, I was all in on this talented, lightly raced son of Candy Ride after his front-end romp in the Grade 1 Runhappy Santa Anita Derby on April 3 at Santa Anita Park.
Then, No. 1 Known Agenda (6-1) started creeping into my picks and I started second guessing myself in the lead-up to the 147th running of the annual “Run for the Roses.” So, after some back-and-forth debate between my ears, I’ve stuck with my first pick and we’re going full steam ahead with Rock Your World.
This horse’s career is eerily similar to 2006 Derby champion Barbaro, who was unbeaten and the definition of brilliant before breaking down at the start of the Preakness that year. Like the great Barbaro, Rock Your World began his career on the turf. Trainer John Sadler then opted to take a shot on the Santa Anita dirt after his charge posted two grass wins, where he was victorious in both outings.
Needless to say, it was the a perfect move by the horse’s connections as he rolled to the victory by 4 ¼ lengths. That performance was good enough for Rock Your World to be tabbed second choice behind unbeaten favorite Essential Quality.
I expect Rock Your World to slightly switch tactics in the Derby, with jockey Joel Rosario likely sitting right off the lead this time out instead of gunning to the front out of the No. 15 post position. That should set the duo up perfectly right off the leaders, which should allow him to make his move around the ¾ pole and kick into high gear coming down the stretch.
Only two Breeders’ Cup Juvenile champions have won the Kentucky Derby (Street Sense in 2007; and, Nyquist in 2016), which is the historical aspect of this race Essential Quality has working against him. I will fade the deserved favorite and hope Rock Your World gets the perfect trip and rolls to the victory.
No. 7 Mandaloun (15-1)
Brad Cox trains the morning line favorite No. 14 Essential Quality, but his “other horse” has been buzzing in workouts leading up to the Kentucky Derby – the No. 7 Mandaloun has been training as well as any horse at Churchill Downs over the past couple of weeks.
Mandaloun was the morning line favorite in each of his five starts to date, including a disappointing sixth place finish in the Louisiana Derby on March 20. His qualifying race – when he earned a 99 Beyer speed figure in the Risen Star in February – is fast enough to compete with this group.
Many of the horses in this field didn’t gain significant racing experience over the past two years, as a result of the pandemic, and I’m inclined to trust recent workouts over a race that took place six weeks ago – because the clunker of a race is an outlier compared to Mandaloun’s recent workouts and past performances.
If you reversed the timing of his past two races – if he was coming off of a win and a career-best figure in this spot – Mandaloun’s price would likely be halved – closer to 8-1 on the morning line.
People like to bet on Derby Horses in good race form – but I’ll take the horse who has been outworking his favored stablemate at more than seven times the price.
Best Kentucky Derby Longshots
No. 6 O Besos (20-1)
O Besos is my best longshot play in this field. He comes in off a third-place finish in the Louisiana Derby, but he was flying late. In that race, O Besos ducked down to the rail and ended up winning the gallop out.
He’s another one who, if he can take another step forward from that race, stands a chance in here at a big price. I will be including him in both vertical and horizontal wagers.
No. 10 Midnight Bourbon (20-1)
When likely pacesetter Caddo River dropped out of the field, it threw a big wrench into the pace scenario for the Derby.
Several horses – including the No. 15 Rock Your World, No. 8 Medina’s Spirit, No. 9 Hot Rod Charlie, No. 17 Highly Motivated, and No. 19 Soup and Sandwich – could attempt to show early speed, but I think the No. 10 Midnight Bourbon has a strong chance to lead the pack after the first turn.
Hall-of-Fame jockey Mike Smith is aboard for Steve Asmussen – who holds the record for most Derby entrants without a Derby win. It’s a matter of time before Asmussen breaks through – and Midnight Bourbon has better odds than the No. 18 Super Stock, who recently won the Arkansas Derby.
I’m not sure if Midnight Bourbon can win the race unless he takes another step forward, but he is consistent (three consecutive Beyer speed scores in the 90s) and I think he has the ability to get an early lead and hang on for the bottom of your trifecta and superfecta tickets.
Best Undercard Longshot
Race 11: No. 2 Count Again (10-1)
Meet my top longshot on the Derby Day card.
I absolutely love Count Again in the deep, nine-horse field for Grade 1 $1 million Old Forester Bourbon Turf Classic Stakes. The 6-year-old gelding by Awesome Again looked fantastic when running third in the Frank E. Kilroe Mile (G1) at Santa Anita Park last time out.
Piloted by jockey Luis Saez, Count Again was second to last when they approached the far turn before launching out a seven-wide move at the top of the stretch. The Ontario (Canada) bred wound up finishing third, less than a length behind eventual winner Hit The Road and runner-up Smooth Like Strait, who is entered in this race as well.
What stuck with me was how Count Again, who has been third or better in eight of his 10 career starts, finished the final furlong of the race. He had more in the tank than anyone else in the field, as witnessed by his gallop out where he clearly could have kept his pace up another eighth of a mile. Now, he gets that extra distance and has a perfect position in the gate to simply drop back, then make that big late move down the lane.
Historically, Count Again clearly prefers running at longer distances. He won the Singspiel Stakes (G3) in September of last year that was run at 1 ¼ miles. Implementing his usual racing style, he sat eighth out of nine horses at ¾ pole before grabbing the lead at the top of the stretch. He won the Seabiscuit Handicap (G2) in November at Del Mar in similar fashion.
I expect Count Again to go off around 10/1 odds, so if we get anything north of that number it will have me even more excited entering this race. Play my upset special across the board (Win-Place-Show), then use him in your exacta and trifecta wagering as listed below.
Best Undercard Bet
Race 6: No. 2 She’s Got You (10-1)
The morning-line favorite for this race is Got Stormy (8-5) for trainer Mark Casse. She has shown a versatile running style, which should prove to help her in this spot. And while she has 11 wins, five seconds and three thirds from 26 career starts, she only has one second-place finish from two starts over this turf course. I’m looking to beat her in the spot.
My top pick is No. 2 She’s Got You (10-1). She has three wins, one second and three thirds from seven career turf starts and has two wins, one second and one third at the distance. She’s Got You is trained by Chad Brown ,and while we haven’t seen her since last year, Brown is winning at a 29% clip off the long layoff.
She’s Got You has some of the best late-pace figures in the race and jockey Javier Castellano should be able to work out a trip for her to get up at the wire.
Race 6: Daily Double (4,5,6 / 2)
The key to this bet is actually in Race 7, the Derby City Distaff – where the No. 4 Gamine is expected to go off as a massive favorite. The Bob Baffert runner is undefeated in one-turn races and is the only horse in her field with triple-digit Beyer speed scores (two raced at 110, one at 108) and early pace.
Gamine is as close as a lock as you will find in a stakes race.
In order to find value on Gamine, I think the best way to play her is in a Daily Double with Race 6, where I only see three or four possible winners. On the contrary, Races 8 and 9 are absolute minefields, and I don’t want to have much exposure (outside of the Pick 5) to those races.
The possible options to start off our Daily Double are the No. 4 Zofelle, the No. 5 Got Stormy, and the No. 6 Blowout – with the latter giving you the best possible ROI. I’ll likely have an extra ticket on the 6 / 2 double with Blowout and Gamine, but I think all three of those horses (4,5,6) are worth using from Race 6.
Just note that a $2 bet will be a $6 ticket (and a $10 bet would be a $30 ticket, etc.) if you include all three options.
Race 10: No. 4 Flagstaff (3-1)
All the hype entering the $500,000 Grade 1, seven-furlong event will be around veteran star Whitmore.
The 8-year-old gelding by Pleasantly Perfect was the 2020 champion male sprinter, who stormed his way to victory in the Grade 1 Breeders’ Cup Sprint.
On paper, he’s the classiest of the bunch without question, yet he’s winless in two starts this year. He finished second in both the Hot Springs Stakes and Count Fleet Sprint Handicap, losing to CZ Rocket on both occasions.
However, the 13-horse field is deep and rich in talent. Suffice it to say, it won’t be a walk in the park for the horse and his connections. Currently the race’s second-betting choice at 7-2 odds, Whitmore will have to deal with morning-line favorite Flagstaff (3-1), who is my top pick on the Derby undercard.
Flagstaff won the Grade III Commonwealth Stakes at Keeneland back in April, plus the 7-year-old son of champion sire Speightstown finished third in the Hot Springs.
For me, this is a huge opportunity for the gelding to flip the script on Whitmore, whom he finished second to in last year’s Count Fleet.
For me, I believe Whitmore has started his regression and his best racing days are behind him. That being said, bet Flagstaff across the board in your win-place-show wagering and play him in a boxed exacta to get invoked with the exotics.