Playing the Odds: Three Kentucky Derby Betting Strategies

I’ll Have Another Kentucky Derby Eclipse Sportswire
Your Kentucky Derby betting strategy should be different if your pick is 15-1, like I’ll Have Another (above), or 3-1 like American Pharoah was in 2015. (Eclipse Sportswire)

For some handicappers, picking the winner of the Kentucky Derby is a badge of honor.

Yet, as much as being correct in the biggest race of the year is a tremendous boost to anyone’s ego, what matters more in gambling is the impact your selections have on your wallet.

If you’re right and you somehow manage to break even or lose money on your wagers, well, your ego will not pay for the gas on the ride home. Conversely, is there anything wrong with watching your selection lose but turning a profit on the race?

Call me a material guy, but I’ll take the cash.

The key to any horse race, be it the Kentucky Derby at Churchill Downs or a $5,000 claimer at Pimlico, is making efficient use of your wagering dollars, and with 20 horses, the Derby can be a mine field for your bankroll.

With that in mind, let’s plot out some strategies for the 142nd edition of the Kentucky Derby.

For starters, unless you have a gargantuan budget, you should focus on one horse.

In a 20-horse field, it’s incredibly easy to fall victim to a costly dose of indecisiveness.

It’s something like this: Yeah, you like Nyquist. So you have to bet him. But you think Mohaymen can bounce back, so you have to cover him. And Brody’s Cause and Exaggerator really looked good in their last race and you can’t leave them out. And a horse from Dubai is going to win the Derby sometime, so Lani needs to be in your tickets. And you can’t leave Bob Baffert out, so you have to include Mor Spirit.  Oh, and with a best friend named Tom, you absolutely have to bet on Mo Tom and Tom’s Ready.  You saw “Spotlight” last night, so you better add Oscar Nominated. And, wait, what was playing on your all-1970s-all-the-time radio station yesterday while you were driving to the track? Wasn’t it Olivia Newton-John’s “Sam?” Well, you have to add My Man Sam, right?

OK, we’re stretching things with that last one, but the point is that it’s easy to come up with a 10-horse exacta box in the Derby and still have some fears that you left out horses such as Gun Runner, Outwork or Destin.

So get focused and pick the one horse you like best, then structure your wagers around his odds, keeping in mind that you should bet Nyquist differently than Oscar Nominated because of the big difference in their price on the toteboard.

The one sure thing about the Derby is that Nyquist will be favored, so let’s start there.

If you like him, you might get a $7 or $8 win payoff, so let’s start with a $20 win bet that will return $70 or $80.

With a relatively small return like that, backing up Nyquist for second or third will only cut into your already small profit if he wins.

The exacta is a risky wager since there are 19 different horses who can finish in the place spot. Instead, to enhance your profit, turn to the Pick 3 that starts two races before the Derby and key Nyquist in the final leg.

The Pick 3 is a better choice than doubles because of a larger payoff and it’s easier to hit with a smaller ticket than a Pick 4.

The proof of that could be seen last year when the favored American Pharoah won the Derby en route to his Triple Crown sweep and paid $7.80 to win. The Pick 3 ending in the Derby paid a nifty $105.60 for $1 and the two winners before him were a $7.40 second choice and $9.40 favorite, making for a relative simple sequence – if you liked American Pharoah.

American Pharoah Kentucky Derby Eclipse Sportswire
American Pharoah winning 2015 Kentucky Derby. (Eclipse Sportswire)

Unless you have a horse you love in the first leg, you should probably use more horses in the first leg than the second. Perhaps a 5 x 4 x 1 ticket for $20 (five horses in the first race, four in the second and one in the third).

By getting through the first leg of a Pick 3, you can then use the double as an insurance policy for horses that you ignored in the second leg, using them with Nyquist to enhance your chances of having a live ticket of some sort to your Derby pick.

With a 20-horse field inflating the pool, if you like favorites in the first two legs of the Pick 3, it would also make sense to spend an extra $4 combining your top two horses in the first two legs with your Derby pick so that you could have a live $2 Pick 3 to the final race – which would have generated a $211.20 payoff a year ago.

Finally, to cover the very distinct possibility that Nyquist loses, close out your wagering with a four-horse exacta box at total of $12 for a $1 base wager.  This way, if your third and fourth choices run 1-2, you will turn a profit.

All told, you are wagering $52 and if you’re right you are guaranteed $70 or $80, which is measly, but you could easily pad that total with another $100 or $200 in the Pick 3 and perhaps $50 or so in the exacta.

After that, it doesn’t really matter which horse you like. It’s the odds that will dictate your strategy. If your horse is somewhere between 3-1 and 5-1, you should follow the same betting strategy as you would with Nyquist. The base return on your $20 win wager does not leave much room for covering a wealth of possibilities.

Once you get up to 6-1 and definitely at 9-1, you should consider dropping the Pick 3 play or the boxed exacta in favor of an exacta wheel using your horse underneath the other 19 horses. This ticket is a loser if your horse wins, but it also allows you to watch the race knowing you are heading to the cashier’s window if your horse finishes first or second.

Sometimes you can even luck into a huge payoff, like you would have in 2009 if you used 6-1 shot Pioneerof the Nile (American Pharoah’s daddy) underneath in an exacta wheel. When Mine That Bird won that year’s Derby at 50-1 odds and everyone else was ripping up tickets, you were heading to the windows with a huge grin and a $2 exacta ticket that was now worth $2,074.80.

Being wrong was never so right.

Kentucky Derby longshot Mine That Bird Eclipse Sportswire
Derby-winning longshot Mine That Bird. (Eclipse Sportswire)

Keep in mind, too, that as the odds on your horse rise, you should also consider putting more money into play.

Realistically, if a favorite like Nyquist wins, unless you make a huge win bet, you are not going to make the kind of money you’ll talk about for years. You’ll probably get more mileage from your chest-thumping about being right than the cash from your winnings. With horses in the 6-1 to 20-1 range, you have enough of a return from the win bet to cover the losses from insurance bets such an underneath exacta wheel.

But with a horse above 20-1, the payoffs in the exotic wagers could be astronomical and it’s worth investing more dollars into the pools. With 20 horses to inflate the pool, you are going to see exacta and triple payoffs vastly different from the mutuels triggered by a 25-1 shot in a typical eight-horse field. Your 25-1 shot will pay off like a 75-1 shot in an average field.

So splurge. Let it ride. Bet a little more to win and aside from the exacta wheel perhaps you should buy a four-horse trifecta box ($24 for $1 bets) or use four horses in the first and second spots in a Pick 3 with your Derby pick singled for third ($12 for $1 bets).

This way, if you’re right, you’ll truly have the right stuff.

And even if you’re wrong, the immense thrill you’ll get from watching the Derby with a live $2,000 or $3,000 Pick 3 ticket on the line is definitely worth the extra $20 or $50 you are risking in a once-every-12-months setting.

So, that’s the game plan. Now it’s up to you to do the heavy lifting and settle on the horse that makes your strategy work.

It will not be easy, but it can be highly rewarding … if you wager as well as you handicap.



Horses at 5-1 or less

$20 to win

$20 in Pick 3 (5 x 4 x 1 for $1)

$12 for 4-horse $1 exacta box

Total: $52


Horses at 6-1 to 20-1

$20 to win

$19 for $1 exacta wheel  (All with 1)

$12 for 4-horse $1 exacta box


$20 in Pick 3 (5 x 4 x 1 for $1)

Total: $51 or $71


Horses above 20-1

$25 to win

$19 for $1 exacta wheel  (All with 1)

$12 for 4-horse $1 exacta box

$20 in Pick 3 (5 x 4 x 1 for $1)

$24 for 4-horse $1 trifecta box or $12 for keying 4 horses in top 2 spots with 1 in 3rd (4 with 4 with 1)

Totals: $100 or $88

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