Betting on the Kentucky Derby: A Gentleman’s Guide

Will Brinson

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It’s Kentucky Derby time, kids, and that means gambling. Well, that and a really exciting 30 seconds or so of horses sprinting around a track, as well as some fortunes won and lost. Also, it means an interview with horse-racing expert and Philadelphia Daily News columnist and national horse-racing reporter Dick Jerardi in order to figure out how to bet on the Derby.

I’ll be in Vegas for this one, and while I don’t want you coming with me, that doesn’t mean you can’t get in on the action. Dick mentions XPressBet.com as a good spot to hit up if you have cash to burn with which to win more cash.

He also breaks down what you can bet on below — specifically the trifecta and the superfecta. However, if you want  to really figure out all the various bets, Handicapping.com has a nice, full guide on all the things you can bet on with a horse race. I literally don’t have time to explain them to you here. And KentuckyDerby.com has all the odds you need — Dialed In is the morning favorite after getting the draw Thursday.

And now, five questions you might be asking about wagering on the Kentucky Derby. (Ed. Note: Yes, some of these are easier questions, but we’re trying to help out the novice as well as the more experienced bettor here.)

Guyism: What’s the most efficient way to put bets down when it comes to horses?
Dick Jerardi: Once you have decided which horse or horses you like best, try to maximize the potential payoff by putting your money into the bet that makes that matches your opinion. If you only like one horse, that would likely mean you should be betting to win. If you like three horses equally, that might be a trifecta.

Guyism: I keep hearing about trifectas and superfectas … what exactly are those and should I be playing them?
Jerardi: Trifectas are the first three horses in order. Superfectas are the first four horses in order. Again, it depends on what you you like in the race. If, say, you don’t like the favorite, but like six other horses in a race, you might try the superfecta as the payoff, if the favorite does not finish in the top four, could potentially be gigantic.

Guyism: I love underdogs and longshots — is it worth betting on the horse that’s 60:1?
Jerardi: Probably not blindly. Horses are 60-1 for a reason. They don’t have much chance. If, however, you evaluate a horse and decide that horse should be around 20-1 and the horse goes off at 60-1, you are getting the best of the odds and probably should make a bet.

Guyism: Are there any cool prop bets like at the Super Bowl?
Jerardi: Some race books have horse vs. horse props, just betting to see which horse finishes ahead of another, regardless of where they finish in relation to the winner. Historically, there is also an over/under time bet.

Guyism: Where’s the best place to bet if I don’t live near a casino?
Jerardi: Xpressbet, the legal, licensed no fee wagering company. You can open an account, deposit some money and play from home on your computer.