Betting a 10-1 Longshot in the 2021 Kentucky Derby

Gambling
Toyota Blue Grass Stakes runner-up Highly Motivated has a chance to pull an upset in the 2021 Kentucky Derby Presented by Woodford Reserve. He is listed at 10-1 odds on the morning line. (Coady Photography)

For handicappers, there’s no greater satisfaction than betting a longshot and seeing your unheralded selection take first prize. Whether it’s a $5,000 claiming race at Mahoning Valley or a Grade 1 stakes, beating the odds and uncovering a longshot winner is much more satisfying than betting a bevy of favorites.

This goes double if the race you’re handicapping is the $3 million, Grade 1 Kentucky Derby Presented by Woodford Reserve at Churchill Downs, because let’s face it — there are bragging rights involved. Millions of people watch the Kentucky Derby every year, even folks who don’t normally follow horse racing. Pick a longshot Kentucky Derby winner, and you’ll be a hero for years.

weekend TV schedule

Thursday, April 29: 12:30 p.m.-6:30 p.m. ET on FS2; post time varies on TVG
Friday, April 30:
12 p.m.-6 p.m. ET on NBCSN; 12 p.m.-5:30 p.m. ET and 8:30 p.m.-9 p.m. on FS2; post time varies on TVG
Saturday, May 1:
12 p.m.-3 p.m. and 4 p.m.-6:30 p.m. on FS2; 12:30 p.m.-2:30 p.m. ET on NBCSN; 2:30 p.m.-7:30 p.m. ET on NBC; post time varies on TVG
Sunday, May 2:
1 p.m.-3 p.m. and 4 p.m.-5:30 p.m. on FS2; post time varies on TVG

Of course, we don’t recommend bragging, but we do recommend betting because the Kentucky Derby is typically the best betting race of the year. With 20 lightly raced Thoroughbreds vying for supremacy over an unfamiliar 1 1/4-mile distance, the historic run for the roses is a recipe for unpredictable outcomes. Even when the favorite visits the winner’s circle, you can typically count on a longshot or two to finish in the top four.

So why not bet a longshot in the 2021 Kentucky Derby? Even more so than usual, the race seems ripe for an upset. Sometimes, the Derby field features four or five above-average horses who have run very fast on the speed-figure scales. When this happens, the results tend to be more predictable — longshot can’t improve enough to challenge the top contenders, and the fast favorites are unlikely to suddenly regress all at the same time.

But other times, the Derby field is more evenly matched. The top contenders come in with modest speed figures, and the longshots aren’t that much slower on paper. Years like these are more likely to produce upset winners — Animal Kingdom at 20.90-1 in 2011 comes readily to mind.

The 2021 Kentucky Derby is shaping up to be one of those evenly matched years. Undefeated #14 Essential Quality has emerged as the 2-1 favorite after showcasing a variety of running styles to win all five of his starts. He originally gained a reputation as a closer after rallying from eighth place to win the Grade 1 TVG Breeders’ Cup Juvenile Presented by Thoroughbred Aftercare Alliance, cementing his status as the champion 2-year-old male of 2020. But Essential Quality also is capable of tracking and pressing the pace, as he did when forging to victory by a neck in the Grade 2 Toyota Blue Grass Stakes four weeks ago.

Essential Quality is hard to knock on paper, but he does have one flaw: a tendency to “paddle” with his left front leg. This stride abnormality hasn’t bothered Essential Quality so far, but it can be a stumbling block for horses stretching out to longer distances. Since Essential Quality has yet to run farther than 1 1/8 miles, the 1 1/4-mile trip of the Kentucky Derby looms a question mark for the Derby favorite.

Other short-priced Kentucky Derby contenders have questions to answer as well. #15 Rock Your World was a flashy gate-to-wire winner of the Grade 1 Runhappy Santa Anita Derby, but he didn’t race as a juvenile, and only one Kentucky Derby winner since 1882 has prevailed without gaining foundation as a 2-year-old. #1 Known Agenda dominated the Grade 1 Curlin Florida Derby Presented by Hill ‘n’ Dale Farm at Xalapa and is bred to excel over the Kentucky Derby distance, but he has a tendency to race greenly and also drew the rail post, which hasn’t produced a Derby winner since 1986.

Acknowledging the uncertainties surrounding the Kentucky Derby favorites, I’m tempted to support a longshot instead. Not necessarily a 50-1 shot, but a nice mid-range horse, somewhere between 10-1 and 20-1. There are plenty of options to consider, but none strike me as more appealing than #17 Highly Motivated, runner-up in the Blue Grass and a horse seemingly poised to fire a huge shot on the first Saturday in May.

Highly Motivated has always shown signs of significant talent. Just look back on his performances last season. In a maiden sprint at Belmont Park, Highly Motivated rallied smartly from just off the pace to defeat none other than Known Agenda by 1 3/4 lengths. Then, in the Nyquist Stakes at Keeneland, Highly Motivated crushed a deep field by 4 1/4 lengths in track-record time.

Following the Nyquist, trainer Chad Brown elected to give Highly Motivated time off, resting him for the remainder of 2021. This patient approach appears to be reaping dividends. Highly Motivated was a little dull in the one-mile, Grade 3 Gotham Stakes to kick off the year, but even with a tricky trip, he was only beaten by 1 3/4 lengths. Then he stepped up in class and distance for the 1 1/8-mile Blue Grass, where he switched to front-running tactics and just barely failed to hold off Essential Quality in a thrilling drive to the finish line.

Highly Motivated actually finished quite fast in the Blue Grass, sprinting the final three-eighths of a mile in :36.45, so there’s no reason to think the Kentucky Derby distance will be an obstacle. Indeed, Highly Motivated figures to run better than ever at Churchill Downs. He should be fit for a peak performance in his third start of the season, and drawing post-position 17 should allow Highly Motivated to work out a perfect trip stalking Rock Your World, a more favorable scenario than the pace-setting tactics he employed in the Blue Grass.

In short, I’m eager to support Highly Motivated as a 10-1 shot in the Kentucky Derby. At this price, even bettors playing on small budgets have a chance to cash big paydays.

Essential Quality, Known Agenda, and Rock Your World are all logical contenders to finish in wagers like the exacta and trifecta, along with Grade 2 Twinspires.com Louisiana Derby first- and third-place finishers #9 Hot Rod Charlie and #6 O Besos. We’ll use them all underneath Highly Motivated, but in varying degrees, depending on how much money you want to spend betting the Kentucky Derby.

Wagering Strategy on a $10 Budget

$4 to win on #17 Highly Motivated

What to say at the betting window: Churchill Downs, 12th race, $4 to win on 17

$1 exacta: 17 with 1,9,14 ($3)

What to say at the betting window: Churchill Downs, 12th race, $1 exacta 17 with 1,9,14

$1 exacta: 1,9,14 with 17 ($3)

What to say at the betting window: Churchill Downs, 12th race, $1 exacta 1,9,14 with 17

Wagering Strategy on a $30 Budget

$15 to win on #17 Highly Motivated

What to say at the betting window: Churchill Downs, 12th race, $15 to win on 17

$2 exacta: 17 with 1,9,14 ($6)

What to say at the betting window: Churchill Downs, 12th race, $2 exacta 17 with 1,9,14

$3 exacta: 1,9,14 with 17 ($9)

What to say at the betting window: Churchill Downs, 12th race, $3 exacta 1,9,14 with 17

Wagering Strategy on a $50 Budget

$14 to win on #17 Highly Motivated

What to say at the betting window: Churchill Downs, 12th race, $14 to win on 17

$2 exacta: 17 with 1,9,14 ($6)

What to say at the betting window: Churchill Downs, 12th race, $2 exacta 17 with 1,9,14

$3 exacta: 1,9,14 with 17 ($9)

What to say at the betting window: Churchill Downs, 12th race, $3 exacta 1,9,14 with 17

$0.50 trifecta: 17 with 1,9,14 with 1,4,5,6,9,14,15,16 ($10.50)

What to say at the betting window: Churchill Downs, 12th race, $0.50 trifecta 17 with 1,9,14 with 1,4,5,6,9,15,16

$0.50 trifecta: 1,9,14 with 17 with 1,4,5,6,9,14,15,16 ($10.50)

What to say at the betting window: Churchill Downs, 12th race, $0.50 trifecta 1,9,14 with 17 with 1,4,5,6,9,15,16

Good luck, and enjoy the race!

2021 Kentucky Derby presented by Woodford Reserve
May 1st, 2021

Winning Time: 2:01.02
  • Purse: $3,000,000
  • Distance: 1 1/4 Miles
  • Age: 3 yo
  • Surface: Dirt
  • Winning Time: 2:01.02
Results
Win
Place
Show
1st
8 Medina Spirit
$26.20
$12.00
$7.60
2nd
7 Mandaloun
$23.00
$13.40
  • Owner / Juddmonte
  • Breeder / Juddmonte Farms Inc
4th
14 Essential Quality
6th
10 Midnight Bourbon
7th
4 Keepmeinmind
8th
12 Helium
  • Owner / D. J. Stable LLC
  • Breeder / Teneri Farm Inc. & Bernardo Alvarez Calderon
9th
1 Known Agenda
10th
17 Highly Motivated
11th
5 Sainthood
12th
2 Like the King
13th
20 Bourbonic
14th
13 Hidden Stash
15th
3 Brooklyn Strong
  • Owner / Mark Schwartz
  • Breeder / Cheryl Prudhomme & Dr. Michael Gallivan
16th
18 Super Stock
17th
15 Rock Your World
18th
11 Dynamic One
19th
19 Soup and Sandwich
Scratches
Payoff
Pick 3
4-5-8
4-5-8
$163
Pick 3
OAKS/FRSTR/DERBY 10-3-8
OAKS/FRSTR/DERBY 10-3-8
$52
Pick 3
4-3-8
4-3-8
$73
Pick 3
OAKS/FRSTR/DERBY 10-5-8
OAKS/FRSTR/DERBY 10-5-8
$109
Pick 4
5-4-3/5-8
5-4-3/5-8
$708
Pick 5
2/3-5-4-3/5-8
2/3-5-4-3/5-8
$2,975
Pick 6
OAKS/DERBY 2-7-10-4-4-3/5-8
OAKS/DERBY 2-7-10-4-4-3/5-8
$2,144
Pick 6
OAKS/DERBY 2-7-10-4-4-3/5-8
OAKS/DERBY 2-7-10-4-4-3/5-8
$22
Pick 6 Jackpot
4-2/3-5-4-3/5-8
4-2/3-5-4-3/5-8
$1,364
Daily Double
OAKS/DERBY 10-8
OAKS/DERBY 10-8
$48
Daily Double
3-8
3-8
$26
Daily Double
5-8
5-8
$63
Exacta
8-7
8-7
$504
Future Wager
POOL 5 - 15
POOL 5 - 15
$29
Future Wager
POOL 4 - 15
POOL 4 - 15
$81
Future Wager
POOL 3 - 15
POOL 3 - 15
$53
Future Wager
EXACTA POOL 2 - 14-13
EXACTA POOL 2 - 14-13
$3,254
Future Wager
SIRE EXACTA 1 - 24-12
SIRE EXACTA 1 - 24-12
$60
Future Wager
EXACTA POOL 3 - 15-14
EXACTA POOL 3 - 15-14
$1,543
Future Wager
POOL 1 - 24
POOL 1 - 24
$5
Future Wager
SIRE POOL 1 - 24
SIRE POOL 1 - 24
$12
Future Wager
POOL 2 - 14
POOL 2 - 14
$51
Future Wager
EXACTA POOL 5 - 15-14
EXACTA POOL 5 - 15-14
$1,774
Future Wager
EXACTA POOL 4 - 15-14
EXACTA POOL 4 - 15-14
$860
Future Wager
EXACTA POOL 1 - 24-7
EXACTA POOL 1 - 24-7
$124
Superfecta
8-7-9-14
8-7-9-14
$9,456
Super High Five
8-7-9-14-6
8-7-9-14-6
$296,770
Trifecta
8-7-9
8-7-9
$848
Race Replay
Play
Payoff
Pick 3
4-5-8
4-5-8
$163
Pick 3
OAKS/FRSTR/DERBY 10-3-8
OAKS/FRSTR/DERBY 10-3-8
$52
Pick 3
4-3-8
4-3-8
$73
Pick 3
OAKS/FRSTR/DERBY 10-5-8
OAKS/FRSTR/DERBY 10-5-8
$109
Pick 4
5-4-3/5-8
5-4-3/5-8
$708
Pick 5
2/3-5-4-3/5-8
2/3-5-4-3/5-8
$2,975
Pick 6
OAKS/DERBY 2-7-10-4-4-3/5-8
OAKS/DERBY 2-7-10-4-4-3/5-8
$2,144
Pick 6
OAKS/DERBY 2-7-10-4-4-3/5-8
OAKS/DERBY 2-7-10-4-4-3/5-8
$22
Pick 6 Jackpot
4-2/3-5-4-3/5-8
4-2/3-5-4-3/5-8
$1,364
Daily Double
OAKS/DERBY 10-8
OAKS/DERBY 10-8
$48
Daily Double
3-8
3-8
$26
Daily Double
5-8
5-8
$63
Exacta
8-7
8-7
$504
Future Wager
POOL 5 - 15
POOL 5 - 15
$29
Future Wager
POOL 4 - 15
POOL 4 - 15
$81
Future Wager
POOL 3 - 15
POOL 3 - 15
$53
Future Wager
EXACTA POOL 2 - 14-13
EXACTA POOL 2 - 14-13
$3,254
Future Wager
SIRE EXACTA 1 - 24-12
SIRE EXACTA 1 - 24-12
$60
Future Wager
EXACTA POOL 3 - 15-14
EXACTA POOL 3 - 15-14
$1,543
Future Wager
POOL 1 - 24
POOL 1 - 24
$5
Future Wager
SIRE POOL 1 - 24
SIRE POOL 1 - 24
$12
Future Wager
POOL 2 - 14
POOL 2 - 14
$51
Future Wager
EXACTA POOL 5 - 15-14
EXACTA POOL 5 - 15-14
$1,774
Future Wager
EXACTA POOL 4 - 15-14
EXACTA POOL 4 - 15-14
$860
Future Wager
EXACTA POOL 1 - 24-7
EXACTA POOL 1 - 24-7
$124
Superfecta
8-7-9-14
8-7-9-14
$9,456
Super High Five
8-7-9-14-6
8-7-9-14-6
$296,770
Trifecta
8-7-9
8-7-9
$848

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