How to bet the 2021 Kentucky Derby on different budgets

Profile Picture: J. Keeler Johnson

May 1st, 2021

In recent years, handicappers have become accustomed to seeing unsurprising outcomes in the Kentucky Derby (G1).

The favorite prevailed in every Derby from 2013 through 2018, while third choice Authentic took top honors last year. In 2016, the top four betting favorites swept the superfecta in order of their odds.

But the 2021 Kentucky Derby is shaping up to be a different kind of affair. The top contenders appear evenly matched on paper and earned similar Brisnet Speed ratings for their best efforts.

The favorites have chinks in their armor. Undefeated #14 Essential Quality (2-1) paddles significantly with his left front leg, Santa Anita Derby (G1) winner #15 Rock Your World (5-1) has only three starts under his belt, and Florida Derby (G1) winner #1 Known Agenda (6-1) tends to race greenly.

I don’t think they’re unbeatable at short prices, and you can even argue Essential Quality and Rock Your World may have peaked in their final prep races.

Since this Kentucky Derby appears ripe for an upset, I’m going to think outside the box, with #17 Highly Motivated (10-1), the Blue Grass runner-up. He was defeated in both of his starts this year, but I’m confident Highly Motivated has been primed to produce a career-best effort on the first Saturday in May.

Highly Motivated showed promise as a juvenile, when he defeated Known Agenda in a maiden race, then dominated Keeneland’s Nyquist S. in track-record time.

Following a winter layoff, Highly Motivated finished a troubled third in the Gotham (G3), then improved sharply to finish a neck behind Essential Quality in the Blue Grass. The latter effort was impressive, since Highly Motivated carved out the pace (not his usual running style) and sprinted the final three furlongs in :36.45.

In the past, trainer Chad Brown has done terrific work with Kentucky Derby contenders who showed promise at age two. Brown’s typical two-prep approach isn’t focused on winning early season stakes. It’s geared toward success on the first Saturday in May. Since 2013, Brown has saddled three Derby starters with form lines similar to Highly Motivated, and all three earned purse money, including 2018 runner-up Good Magic.

Highly Motivated has drawn perfectly in post 17, which sets the stage for an ideal stalking trip, behind Rock Your World. If Highly Motivated steps forward the way I believe he will, he can upset the Kentucky Derby at enticing odds.

#4 Keepmeinmind (50-1), #5 Sainthood (50-1), #6 O Besos (20-1), and #9 Hot Rod Charlie (8-1) are others we’ll support in exotic wagers. We’ll emphasize Hot Rod Charlie, who won the Louisiana Derby (G2) with a forwardly placed trip.

Depending on the budget you’ve allocated for betting the Kentucky Derby, we’ve outlined three wagering strategies at costs of $30, $60, and $100.

$30 budget

Betting exactas in the Kentucky Derby is a budget-friendly strategy, but one with the potential to produce solid returns. When 15-1 shot I’ll Have Another beat 21-5 favorite Bodemeister in 2012, the $1 exacta returned $153.30.

$12 to win on #17 Highly Motivated
$2 exacta: 17 with 1,9,14 ($6)
$4 exacta: 1,9,14 with 17 ($12)

$60 budget

Trifecta tickets are more expensive to play, but they significantly increase the potential for a big payoff. In 2012, 12-1 shot Dullahan rounded out the trifecta, behind I’ll Have Another and Bodemeister, a reasonably logical outcome that paid $1,532.80 for every $1 ticket.

$18 to win on #17 Highly Motivated
50-cent trifecta: 17 with 1,9,14 with 1,4,5,6,9,14,15,16 ($10.5)
50-cent trifecta: 17 with 1,4,5,6,9,14,15,16 with 1,9,14 ($10.5)
$1 trifecta: 1,9,14 with 17 with 1,4,5,6,9,14,15,16 ($21)

$100 budget

Hitting a Kentucky Derby superfecta is one of the hardest betting challenges in racing. The minimum wager amount is $1, so ticket costs increase sharply with each additional horse you use.

But the rewards can be massive, since it’s common for longshots to crash the Kentucky Derby top four. When 30-1 outsider Went the Day Well completed the superfecta in the 2012 Kentucky Derby, the $1 payoff was $48,046.40.

$28 to win on #17 Highly Motivated
$1 superfecta: 17 with 1,9,14 with 1,9,14 with 1,4,5,6,9,14,15,16 ($36)
$1 superfecta: 17 with 1,9,14 with 1,4,5,6,9,14,15,16 with 1,9,14 ($36)

Good luck!