How To Bet The 2016 Kentucky Derby

TAGs: Exaggerator, Gun Runner, horse betting, Kentucky Derby, Mo Tom, Mohaymen, Mor Spirit, Nick Gianatis, Nyquist

How To Bet The 2016 Kentucky DerbyThe 142nd renewal of the Kentucky Derby will run on May 7th and even if you’re not the biggest fan of horse racing, you’ll be interested in what happens because most people reading this website are gamblers. Any opportunity to win money is going to draw intrigue. Few are as fun, or as thrilling, as the Kentucky Derby.

Next week I’m going to give a thorough breakdown of the best ways to bet the Kentucky Derby but for now I’m going to give you a crash course. This is everything you need to know about betting on horses and the main threats in the Kentucky Derby field.

Betting on Horses 101

The absolute best part about betting on horses, if you didn’t know already, is that you don’t necessarily have to bet on the straight up winner. That tends to pay the most, but you can also safely hedge your bets by betting on horses to finish in the top-2 or the top-3.

Straight bets are the most commonplace wager in horse betting, but exotics have their place as well. You can bet on the top-2 or top-3 horses in order or in general, with the more specific wager paying out higher. Let’s explain this in case by case detail.

Straight Bets (One Horse)

A straight bet is a wager on one horse generating a single result.

Win – The horse must run and finish 1st.

Place – The horse must run and finish 1st or 2nd.

Show – The horse must run and finish 1st, 2nd or 3rd.

Depending on which straight bet you take, the odds are modified. It is easier to win a show bet because of the triple outcome, and with reduced risk comes a slightly lesser reward. Betting on a horse to win outright always has the highest payout all odds being even.

Exotic Bets (Multiple Horses)

Exotic horse bets include any wager where multiple straight bets are tied together.

Exacta – Your horses must finish 1st and 2nd in a specified order. This makes the bet much harder to win but also greatly increases the payout.

Trifecta – Your horses must finish 1st, 2nd and 3rd in exact order.

Superfecta – Your select four horses that must finish 1st, 2nd, 3rd and 4th in exact order. The superfecta is the most difficult bet to win in all of horse betting, and is thus the most rewarding. Think of it like betting on a four-team parlay.

Box – “Boxing” an exotic horse bet means that you are betting on the top-2, top-3 or top-4 finishers of a race in no specific order. It is a way of reducing risk, but still generating a large payout. In the case of an exacta box, you are not betting in which horse finishes 1st and 2nd, you are betting on which two horses finish in the top-2. The same logic is applied in a Trifecta Box and a Superfecta Box.


The official market for the futures market is run by Churchill Downs Interactive, the main pipeline for betting on the Kentucky Derby. They have released four different windows over the course of the racing season which have updated the odds for each horse. Let’s take a look at some of the top contenders.

HorsePool 1 (Nov. 29)Pool 2 (Feb.14)Pool 3 (Mar 13)Pool 4 (Apr. 3)
Mor Spirit31/112/112/111/1
Mo Tomn/a28/115/117/1
Gun Runner57/125/125/113/1
Danzing Candyn/a28/117/116/1

As you can see, Nyquist went from being the horse of choice, to losing his top spot to Mohaymen. Eventually he earned his spot back. I’ll explain why as we delve through the contenders for the 2016 Kentucky Derby. But this gives you an idea of how horses have changed value over time as they pick up wins.


The Kentucky Derby has a massive field of 20 horses and there are usually one or two scratches on race day which take out some of the competitors due to health reasons. Obviously, some horses are built better than others and no horse has enjoyed a better Triple Crown preseason than Nyquist. The best part? He only needed one big race to make his case.

NYQUIST (+300 to win the Kentucky Derby)

Best Options – Bet To Win, Build All Boxes Around Him

Nyquist is undoubtedly the horse to beat at the Kentucky Derby. He posted a career defining win at the Breeders’ Cup Juvenile last year in a race run for the top two-year old colts that are ready for competition. He has been slow played through the prep for the Triple Crown to keep him fresh, and the plan has worked magnificently.

Facing his largest hurdle of the season, Nyquist needed to finish in the top-two at the Florida Derby to earn enough points to crack the Kentucky Derby field. He didn’t disappoint, vanquishing a field that included the new, early favorite in the form of Mohaymen. It wasn’t even remotely close.

There have been doubts about Nyquist’s ability over the last few months because he hasn’t run in that many races, but it’s working to his benefit now. He should be your choice to win, and you can safely build boxes around him given his undefeated status.

MOHAYMEN (+1000 to win the Kentucky Derby)

Best Options – Bet To Win or Place

Mohaymen blossomed towards the end of 2015, winning a maiden in September before crushing the Nashua, Remsen, Holy Bull and Fountain of Youth. Even if you’ve never heard of those stakes races, the important things to know are that they’re all run over a mile (the Kentucky Derby is 1 1/4th miles) and all featured some outside contenders worthy of praise.

During this stretch, the aforementioned Nyquist was merely training and Mohaymen thundered to the head of the pack becoming the new favorite for the Triple Crown and the Kentucky Derby. It lasted for about two months until they met at Gulfstream Park. Their showdown at the 2016 Florida Derby was a veritable disaster with Mohaymen falling all the way to fourth.

There’s something to be said about the dichotomous schedules of the two top horses. While Nyquist has been resting and waiting in the wings after proving what he’s capable of early in his two-year old season, Mohaymen had to get in to race shape through late 2015 and early 2016.

Legitimate fears exist that Mohaymen has run too much already. Very rarely does a horse take part in five Kentucky Derby prep races. More often, horses participate in around two or three. Mohaymen looked absolutely burnt out by the time the Florida Derby ran so it will be interesting to see if he’s capable of recapturing his old form in time for the Triple Crown.

It’s safer to make Mohaymen a standalone bet instead of tying him in to a box. There’s no doubt that his talent will draw money with a 10/1 number like that, but whether or not he has anything left in the tank to prove how good he actually is when it matters remains to be seen.

MOR SPIRIT (+1800 to win the Kentucky Derby)

Best Options – Box Bet Option

Bob Baffert is a legend as a four-time winner of the Kentucky Derby and perhaps the greatest trainer in all of thoroughbred racing. He was at the helm of American Pharoah’s triumphant Triple Crown title last year. So any horse that he submits gets automatic notice.

The overhanging issue with Mor Spirit is that he hasn’t come through when it really matters. He has three wins overall but also has four second-place finishes. To be fair, his second place finish at the Santa Anita Derby had more to do with the sloppy conditions the race was run in.

One of the reasons that people like Mor Spirit is that he looks like he’s capable of really pushing a longer race. The Kentucky Derby, Preakness Stakes and Belmont Stakes are three of the longest races that these horses will ever challenge. It’s a lot to risk on a horse who hasn’t always shown that competitive fire to beat out his competition, but the talent is certainly there. Whether you’re willing to take a chance on him proving that distance is his friend is up to you.

MO TOM (+1800 to win the Kentucky Derby)

Best Options – Box Bet Option

Mo Tom is one of my favorite under-the-radar horses. The Thomas Amoss trainee has been flat out screwed in his last two races, where he finished 4th at the Louisiana Derby and 3rd at the Risen Star Stakes. A little more luck and this horse has a chance to take the cake.

In both of the mentioned races, Mo Tom was checked hard (meaning that he was cut off and had to slow down) both times. He’s the type of horse that stalks and waits for the home stretch to really empty the gas tank. Given an uninterrupted line, Mo Tom has a genuine shot at stealing the Kentucky Derby.

Whether he can find one is another question. The Kentucky Derby is a dense field of the best three-year olds in the United States. I don’t love that he hasn’t found his way through traffic just yet. Fool me once, shame on you. Fool me twice…well, you’re not getting my money anymore after that.

EXAGGERATOR (+800 to win the Kentucky Derby)

Best Option – To Show, Box Option Bet

Either the public has heavily targeted Exaggerator or the oddsmakers are very nervous about Exaggerator actually being as good as he was at the Santa Anita Derby. Both have seemingly caved in Exaggerator’s odds, making him the second favorite in most markets. How come? Exaggerator’s Santa Anita Derby victory was one of the fastest ratings we’ve seen this year in the three-year old class.

It did seem like a bit of an anomaly though. Exaggerator was blazing in that race, but he was also a distant third in the San Felipe Stakes and second at the San Vicente Stakes (which is more of a sprint than a miler).

Exaggerator feels like the “hot horse of the moment” rather than someone you should be betting on to win a massive race.

OUTWORK (+2000 to win Kentucky Derby)

Best Option – To Win In Terrible Weather

Running in mud is an absolute skill. Some horses can manage, and others fall far short. Outwork proved what he’s capable of by finishing first at the Wood Memorial in the muck, very much living up to his namesake. There are lots of earlier bets that you can make, but if you wake up on the morning of Saturday, May 7th to find that it’s pouring at Churchill Downs, then Outwork deserves some very heavy consideration.

GUN RUNNER (+1000 to win Kentucky Derby)

Best Option – Exacta Bet With Nqyuist

The leader in the Kentucky Derby points race is pretty unexpected. Gun Runner wasn’t supposed to win the Risen Star Stakes or the Louisiana Derby, but he did both in convincing fashion. Due to the distance of the Kentucky Derby’s homestretch, talent usually prevails but something has to be said about the horse that takes the best line.

In both of his wins, Gun Runner has done exactly that with precise timing and execution. Gun Runner also has exceptional pedigree after being sired by Candy Ride and has proven that he has that competitive edge that’s hard to determine in other races. That’s why his odds are starting to slope downwards. I like him a lot, but not enough to beat Nyquist.

TOM’S READY (+5000 to win Kentucky Derby)

Best Option – To Show as Longshot

There is always a horse with long odds that finishes in the top three at the Kentucky Derby, and one of my favorite choices this year is Tom’s Ready. He’s trained by Dallas Stewart who has had two 50/1 horses finish second at the Run for the Roses already. Commanding Curve did so in 2014 a year after Golden Soul accomplished the same feat in 2013. Stewart has also trained Tale of Verve to a second place finish at the 2015 Preakness Stakes as a 30/1 longshot as well as Macho Again in 2008 at 40/1 in the same race. Grooming longshots at massive races is sort of what Dallas Stewart does.

That’s why a standalone straight bet on Tom’s Ready, or even a brave box bet with Nyquist and him to finish top-two, isn’t so far fetched. Tom’s Ready has finished second at the Louisiana Derby, Lecomte and the Street Sense. Betting on him to win outright actually feels like a genuine way to throw money in the garbage. But a singular place bet to finish in the top-2 at 50/1 is just too tempting to ignore.

I’ll be back next week with more specific outlines of my favorite wagers for the Kentucky Derby. Until then, keep your ear on the rail.



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