Kentucky Derby Betting – Handicapping the Kentucky Derby

Last updated Jul 23, 2021 | Horse Betting

How to Find a Key Horse That Can Lead to Boxcar Derby Payoffs

The Kentucky Derby offers one of the best betting opportunities not just in horseracing, but in all of sports. Dumb, scared, crazy money scorches through the betting windows at a searing pace and the whole town of Louisville, Kentucky turns into one obscene nightmare – or dream – depending on what side of the ledger you’re on.

Nobody has ever or will ever, describe the Kentucky Derby experience as well as the late great Hunter S. Thompson’s did in his 1970 story “The Kentucky Derby is Decadent and Depraved.”

“Just pretend you’re visiting a huge outdoor loony bin,” said Thompson. “If the inmates get out of control we’ll soak them down with Mace.”

If you have a chance to escape to the Kentucky Derby at Churchill Downs just once in your lifetime – you must go. Not just for the betting opportunities and a chance at a life-changing payoff, but for the surreal experience. Just be sure to do your serious handicapping before any heavy drinking or loss of consciousness.

How good can the Kentucky Derby payoffs be? Well, considering that favorites have won only three of the last 20 Derbies, they can be extremely lucrative. And even when the favorites do win, the exotics can still pay boxcars.

In 2007, when favorite Street Sense won the Derby and paid $11.80, the $2 Derby Superfecta paid $29,046.40. That was with second choice Curlin finishing third. The 2006 Kentucky Derby superfecta paid even better when second choice Barbaro won and paid $14.20, topping a pair of $2 Derby superfectas (there was a dead heat for fourth) that paid $84,860.40 and $59,839.00. The latter superfecta had third choice Brother Derek finishing in a dead heat for fourth.

Suffice to say that if you can find a key horse, you’ll get odds that are better than they should be, and you might just latch on to some monster payoffs. There’s just too much uninformed money in the betting pools not to make a profit on Derby day if you handicap reasonably well.

And because the payoffs can be so huge, you don’t necessarily need to find a key horse that can win the Derby – you just need a horse that can finish in the money. You want to be able to part-wheel that horse with a number of other contenders and longshot plodders in exactas, trifectas and superfectas – everywhere. You’re hoping that longshots will come in with your horse and trigger the ultimate boxcar payoff.

Finding your Key Horse in the Kentucky Derby

All we have to go on is history, but combining that with decent handicapping skills will give us a better shot than 90 percent of the crazies that will be betting house numbers, birthdays, names, colors and just about anything else you can think of on Derby Day, including horses that wink at people in the post parade.

Favorites and Speed Rarely Win

Since favorites rarely win the Kentucky Derby for a variety of reasons including big, bulky fields, first time at the distance, traffic trouble, pressure, class issues etc. we’ll be looking to get the favorite and wise guy horses beat. Favorites, while still paying decent when they win, are often over bet in the Derby, as are horses that heat up in the betting just prior to the race for illogical reasons. A good work followed by a few bandwagon newspaper stories and all of a sudden everyone and their pet fruit bat is betting on the horse. No thanks, we’ll be looking elsewhere.

We’ll also be betting against the speed in most cases. Only three horses have been able to take the Derby field wire-to-wire in the last 20 years. If you really think a horse is the total lone speed in the Derby, try to determine whether the horse can clear early and maintain a two-length lead for the first six furlongs while setting only a moderate pace. If a horse can do that they have a chance, usually at good odds. Otherwise forget it. Rallying types rule the Kentucky Derby.

Horses within 1-3 lengths of the leaders win more than their share at the Derby, but often move too early on the pacesetters and end up battling through part of the final turn and into the stretch, tiring late and setting the race up for ralliers and deep closers. We’ll be using a longshot deep closers and rally types on the majority of our superfecta tickets.

Class and Seasoning Major Handicapping Factors

Class and seasoning are the next two areas we’ll be looking at. We want a horse that has started at least twice at two and preferably won or at least been competitive in stakes races at that age. The horse must also have started at least three times at three and won a stakes race. Ten of the last 20 Derby winners won a stake at two and 16 of the last 20 Derby winners won a stakes race at three.

A strong showing at a mile and an eighth at some point prior to the Derby is a must. Nineteen of the last 20 Derby winners have had run a good race at a mile and an eighth prior to the Derby. When horses go beyond a mile and a sixteenth, distance limitations really start to show up. If a horse can’t get a mile and an eighth, they certainly won’t get the mile and a quarter of the Kentucky Derby, even in lesser company.

Poor Works Better Handicapping Angle than Fast Works

Many handicappers and reporters jump all over horses that are working well during Derby week, but the opposite approach may be better. After all, you have 20 of the best 3-year-old thoroughbreds on the planet gathered in one place. How would you expect them to work?

A better handicapping angle that can help you separate the contenders from the pretenders is horses that are not working well or not working at all. Many horses cannot handle the heavy training and racing grind prior to the Derby and start to go off form. This can show up at Churchill Downs in the form of dull works or no works prior to the big race. It’s a tough beat getting to the Derby, and even tougher to get through the Triple Crown races. Watch closely for horses that are going off form and throw them out.


Horses that always work moderately will be fine continuing to work that way during Derby week, but horses that generally work fast who all of a sudden start working slow, could be trying to tell you something. Clocker’s reports are generally decent indicators of poor works and are worth following. They sometimes not only provide the quality of the works, but also some insights into a horse’s general physical condition.

A horse that works average but looks great on the track – dappled and in good flesh – could be in prime shape and ready to run the race of a lifetime. Look for a solid work or breeze of five or six furlongs before the Derby, with a four furlong work being acceptable if the horse has a sharp trainer, is in good form and is proven at route.

Watch Key Derby Prep Races Closely

Horses don’t need to win their final prep race to win the Kentucky Derby, but they do need to run well. They are continually moving up in class prior to the Derby and their final preps often represent yet another new class level Many horses need a race at a new class level before being able to win, and a big race on the raise is often a sign of an impending good race, especially among 3-year-old males.

There are a number of key Kentucky Derby preps, the most important being the Wood Memorial, Santa Anita Derby, Florida Derby, San Felipe and Blue Grass. Winners have also come out of the Arkansas Derby, Fountain of Youth, Lexington, Louisiana Derby Santa Catalina, San Rafael and Lane’s End.

Any horse that can get within four lengths in a key prep race for the Derby deserves a second look, especially if the horse made a bid to win the race. A decent late rally to get within four lengths in an important prep could mean the horse is perfectly suited to the longer distance of the Derby. Not only might the horse have a chance to win, but they can fill out one of your superfecta slots. Even better is a horse that makes a strong stretch bid to win their prep race, only to tire late. These genuine types are sometimes overlooked in the betting and can improve on Derby day.

Beware of Romping Winners

Horses we like to avoid in the win spot in the Derby are those coming into the race off numerous romping wins. Not only are these horses over bet, they generally do not get enough out of their prep races to be fit enough to win the Derby.

Many handicappers make the mistake of thinking that because a horse has scored a romping win at a mile and an eighth, that the horse has reached peak fitness. But horses that win easily do not reach the same fitness levels as horses that are forced to work hard to win their races. Not only do hard races prepare a horse physically for the Derby, they also prepare them mentally for the kind of severe pressure they will face for the first time in their lives at Churchill Downs. Horses that have never had to work to win a race will generally find themselves lacking in both fitness and class in the long Derby stretch run.

A key point to remember is that peak fitness is not only a product of distance races and works, but also of race pressure. The more a horse has to exert itself to win, the fitter it will become. In the Derby stretch run, when fatigue is setting in and horses must rise to a new level of fitness and class to win, you want the horses that are proven fighters – those who have shown the ability to find more when there is nothing left in the tank. While class and fitness are important factors in any handicapping exercise, they are extremely valuable in the Kentucky Derby, especially when blended with courage.

Class + Fitness + Courage = Winner as Heart Trumps Numbers

The heart factor is immeasurable in more ways than one, which makes it an exceptional betting angle. Its appearance in a race is not always recorded in racing publications and many bettors fail to recognize or appreciate it when they see it. Suffice to say, horses with heart will defeat horses with better numbers 80 percent of the time if they can get close to them in the stretch, especially in high class race like the Kentucky Derby, which requires a whole new level of courage. The Derby is not a race for the faint of heart – especially those romping prep-race winners who have yet to prove themselves under fire.

Keeping in mind the fine edge that courage provides, horses must still have a minimum level of ability to be competitive in the Kentucky Derby. Beyer Speed Figures are the best way to measure that ability. We’ll be looking for horses that have cracked the 100 Beyer mark at least once in their lives and preferably run 105 or higher. Keep in mind that the horse with the top Beyer Figure coming into the Derby often loses, possibly because a number of runners may still be improving. Horses that have run a lifetime best Beyer Speed Figure in their race prior to the Derby can and do improve enough to win the big prize.

Outside Posts Better Than Inside

Many bettors think that outside posts can hurt a Derby runner but in fact an outside post is probably better than an inside post and is at least as good as a middle post. Five of the last seven Kentucky Derby winners have come from posts 15-17. Speed horses breaking from inside and middle posts that are not able to establish a good position early often get shuffled back and fall victim to all kinds of trouble. While horses in the outside posts may have the disadvantage of being wide early, it is much easier for them to avoid trouble. Horses that come from off the pace can probably perform equally well from any post, although the inside does tend to result in more trouble early. In any case, a skilled jockey can make a huge difference.

Jockeys and Trainers – Experience Required

We won’t bet a Derby horse to win unless a top jockey is aboard. Jockeys riding for the first time in the Derby are often overwhelmed by the magnitude of the race and the size of the field. We’ll be looking for a well established “A” circuit rider on our key horse or at the very least an exceptional rider from the “B” level track. The same goes for trainers. Rookie trainers (and even veterans) have a difficult time with the Derby pressure and seem to make uncharacteristic mistakes. We always hope our top selection on form has a trainer who has conditioned a horse to win or run in the money in a previous Derby or at least has a very good win percentage in stakes races – preferably graded route stakes.

Dosage a Minor Factor

As far as pedigree goes we’ll be looking for a horse with a dosage of 4.0 or less but won’t throw a horse out unless their dosage is over 6.0. We definitely prefer to use current form, class and heart over a statistical number and do not consider Dosage on its own to be a major handicapping factor (although you’ll see lots written about how important it is.)

Kentucky Derby Betting Summary – Bring Your Wheelbarrow

There are only two horse racing days a year in North America when you truly have an excellent chance of making a monster score for a modest outlay of cash – Breeders’ Cup Day and Derby Day. Watch the prep races closely prior to handicapping and betting the Kentucky Derby – look for courage under fire and apply the principles above. You’ll find your key horse. A horse you can wheel – all the way to the bank.

Bring your wheelbarrow.

(This article was originally written in 2008)