Kentucky Derby Wagering Strategies
Ideas and approaches from the HRF Crew
Level: Intermediate

Note: If you’re not familiar with wagers beyond win, place and show start with our explanation of wager types, but come back!

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Big race days are fun. Not only because big races tend to be exciting, but because there’s a lot more money in the pools than on a regular race day. And why is this fun? Because it means your garden variety exotic payout is going to be higher… and potentially much higher!

For example, the 2009 Kentucky Derby trifecta paid $41,500.60 (chart)! This is the kind of thing that motivates me to 1) play exotics and 2) include longshots. So, what are some ways that you can try to have some fun with exotics on a big race day? Let’s explore some options.

Decide Who You Like
The first thing I try to decide is which horses I like, not only who I think will/can win (and that might be more than one horse), but who could be be in the money… and when I say who, I mean who at a decent price. Do I think that the pace will fall apart and that crazy 20-1 shot closer could clunk up for third or fourth? Do I think that the crazy longshot front-runner could hold on for a piece of the action? Or do I think that a combo platter of nice 8-1 to 15-1 shots have a reasonable chance of being in the money?

Depending on what I decide, here are the approaches I take. Some of them are in my regular rotation and some I only really use on big race days.

Boxes are not only for shoes
If I really like a couple of horses I’m going to box. This is an angle I always play. A $2 three-horse exacta box is $12 and a three-horse $2 trifecta box is $12. If you played both for $24 and you hit at least one of them, you’re more than likely not only to cover your bet but make a little something… and in the case of the Derby, you might make a whole lot more than a little something. This is an easy way to take a shot at some nice returns. You can also do these as $1 or $.50 wagers to cut the price (and payout) down ($12/$6)… better to be in the action than not at all!

Another strategy with exactas is playing strategic combinations for higher amounts. I’m fan of this approach as well, especially on a big day. For example, let’s say you like two horses a lot and two horses a little. You could do a $5 or $10 exacta box of the two you like and then put the two you kind of like underneath the two you really like. It would look something like this where 1 & 2 are the ones you like more and 3 & 4 are the ones you like a little.

$5 exacta box of 1 & 2 = $10
$2 exacta of 1,2/3,4 = $8
$2 trifecta of 1,2/1,2/3,4 = $8
Total = $26

For roughly the same cost as boxing you can back a stronger opinion about two horses and still include some horses you might have a good feeling about. And if those horses are a decent price you could end up with a nice little score!

There’s a reason the word “super” is included
The minimum for superfectas on Kentucky Derby day is a $1. It’s easier to get involved in the superfecta when the minimum is $.10 but there are still a few ways to have fun and not break the bank.

$1 superfecta of 1/2,3,4/2,3,4/2,3,4 = $6 (1 x 3 x 3 x 3)
Add an additional horse in last three positions and make it $24. (1x4x4x4)

$1 superfecta of 1/2,3,4/2,3,4/2,3,4,5 = $12 (1 x 3 x 3 x 4)
One horse over three others + an extra horse in the fourth position

$1 superfecta of 1/2,3/2,3,4,5/4,5,6,7 = $20
1 x 2 x 4 x 5

Considering that the $1 superfecta in the 2010 Kentucky Oaks (chart) paid $2,050.20 with an overwhelming favorite on top, it might worth considering this approach if it fits with your selections!

Casting a wide trifecta net
Here’s one I usually only do on big race days. The final execution depends on how many horses I like to win and how many horses I think have a shot at being in the money but for the sake of example I’ll do two scenarios.

One horse to win, two in the second position and everyone else in the bottom:

$1 trifecta 1x2x17 = $38

I call this one swimming with my mouth open. I’d have to feel pretty darn strong about the the order of the top two AND the preferably the odds of either the top or second two would include a nice price, but if your selections indicate it a play like this it could be an affordable way to shoot for the moon.

Two horses on top, five horses in second and seven in the third.

$1 trifecta 2x5x7 = $40

I’m more likely to take this kind of approach with two on top and less on the bottom. Churchill is making up for no dime supers with .50 trifectas and Pick 3s, you could cut your price in half with either of these approaches!

If you’d like to take advantage of the .50 Pick 3s, be sure to check out Kevin Martin’s excellent piece on simple and effective strategies for multi-race exotics. And if you like to stick to the basics, check out the also helpful Finding Value in the Basics and Longshots Across the Board.

Thoughts on on 2013 Kentucky Derby Wagering Strategy from the HRF Crew
We’ll add more as they come in

Chris Rossi
I’ve got a couple strong opinions on the Derby which I’ll wager around. When the weather is questionable like today, I’ll watch closely and probably bet less if it’s an off track. I’m against Goldenscents on pedigree, regardless of track bias. I think Normandy Invasion is going to bet too much, so no value there for a horse who’s probably an outsider in this field. Orb is a nice horse but has had some trouble free trips, don’t like him much relative to the massive steam surrounding him this week. Overanalyze offers a bit of value and I’ll use him up and down in exotics. Revolutionary is probably the most likely winner regardless of track condition but will not offer any value, I’ll reluctantly include him in all my wagers. Java’s War appears to be the forgotten horse in the press this week, bred for the distance and he’s a smallish colt that will probably skip over an off track. If it’s soupy, I’ll back him on top. All three of those – Revolutionary, Overanalyze and Java’s War are primary horses for me. I’ll play around underneath with Charming Kitten, Palace Malice and Oxbow underneath but not on top as pure pedigree plays.

Kevin Martin
Revolutionary is my pick for win honors in this year’s Derby. I will bet him to win and play him in an exacta and trifecta. My top four is rounded out by Goldencents, Orb, and Java’s War. I will box my top four in an exacta. I will play a trifecta with my top two picks (Revolutionary and Goldencents) keyed in the win position and play six underneath in the second and third position adding Will Take Charge and Normandy Invasion to my top four. Considering the amount of early money invested in Revolutionary, its possible that the morning line 10-1 will be cut in half and he could be the post-time favorite. While I hoped for 8-1, I can live with 5-1 if he performs as I expect him too. Bragging rights for picking a Derby winner trumps what it pays at the windows.

Thoughts on 2012 Derby Wagering Strategy from the HRF Crew
We’ll add more as they come in.

Adam Wiener
I will be dividing my wagering into two distinct groups this year.

I fully expect Dullahan and Alpha to hit the board. Can either win? I believe that is solely determined by the placement of Bodemeister.

If Mike Smith can get his horse to the lead by the first turn, I am convinced this race is over. I will key him in exotics with not only Dullahan and Alpha, but also Daddy Nose Best and Hansen (who I believe will stalk this race despite his prior running styles).

If Bodemeister cannot make the lead, then I think an unbearable pace will develop, breaking apart at the top of the stretch. Therefore, I will create separate tickets constructed solely with those other four horses.

As with every Kentucky Derby, a large field guarantees large prices, allowing me to play a few WPS (win, place, show) bets: Went the Day Well, El Padrino and Sabercat.

I am playing against the buzz of Union Rags, Gemologist and I’ll Have Another. I don’t believe Union Rags is fast enough, while Gemologist (despite pedigree) would have lost to Alpha had their prior battle been longer. Finally, I’ll Have Another had a perfect trip in the Santa Anita Derby, which he will not get here in a speedy, 20-horse field. The only horse I fear not involving is Creative Cause, but my concerns about how his travel ordeal impacted workouts gives me pause.

Kevin Martin
My pick to win this year’s Derby is Union Rags. Not very creative considering he will be the post time favorite but all signs point to a big performance on Derby day. I will put a win bet on Union Rags and use him on exacta and trifecta tickets. The four others that I will lean on in the exotics are Dullahan, Creative Cause, Take Charge Indy and Daddy Nose Best. I’ll play an exacta with Union Rags keyed on the top and bottom with those four. My plan is to punch a few extra exacta tickets with Dullahan, Creative Cause, and Union Rags so if any of those three finish first and second I’ll cash multiple exacta tickets. I will also play trifecta tickets built around my top five and a few tickets with Rousing Sermon, I’ll Have Another and Sabercat keyed underneath.

Chris Rossi
Gemologist checks off more boxes than others. But that’s not a particularly strong opinion. He likes the track, bred for the trip, showed the intangible ‘heart’ in turning back Alpha in the Wood. And, hey, he’s never lost. I just can’t go against that many positives. My strong opinion on the race is that Union Rags may have trouble with the distance and hasn’t taken the step forward this year that I would have expected based on his races last year. Union Rags reminds me of Grace Hall yesterday in Oaks – perhaps the wins in the past performance line are inflating the perception of the horse more than the losses. I want to like Creative Cause but he’s a push button horse who may not be at his best at 10F despite having the breeding to get it. Have to respect the speed of Bodemeister, horses don’t win Grade 1 races by 10 lengths often. That is just too scary to leave off my tickets. I love how Dullahan has improved in his two starts this year and a natural progression puts him on my tickets. I’ll play around with Done Talking, El Padrino and Hansen underneath but I’ll key around Bodemeister, Dullahan and Gemologist on top.

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2 Replies

Can this still be done wagering on the 2014 Kentucky Derby?

Jimmy said on 02 May 2014 at 12:46 pm | Permalink


Hi Jimmy, yes! I’ve updated the post to link to our 2014 Derby content and you can still sign up for a TwinSpires account an play along… best of luck!

Dana Byerly said on 02 May 2014 at 8:04 pm | Permalink



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