My Annual Kentucky Derby Picks

(Photo: John Athayde)

I make public predictions about anything exactly three times a year: who will win each of the three Triple Crown thoroughbred horse races.  Other than that, I predict nothing.

The nice thing about making so few predictions is that by the time next year’s predictions roll around, no one can remember how last year’s predictions turned out.  My very worst year, I named with confidence the horse that I believed would finish dead last, when in fact that horse won the race!  Nonetheless, people still asked me for my picks the next year.

This year, I even got invited to do a live Q&A on the Kentucky Derby, which you can check out at Deadspin.

So who do I like this year in the Kentucky Derby?  My top choice is a horse called Chitu.   His morning line odds are 20-1, and my model predicts he will be at about those same odds at race time.

There are another 6 horses in the 20 horse field I will also play in my exotic bets: Wildcat Red, Vicar’s In Trouble, General A Rod, Wicked Strong, Candy Boy, and Vinceremos.

My model says that the overwhelming favorite California Chrome is not such a bad bet either. But in races like the Kentucky Derby, where there is so much attention and so many horses, I have a general rule to steer clear of prohibitive favorites.  I think it is very easy for a herd mentality to take over (not among the horses, but among the bettors), which makes me feel like the favorites are bad bets.  People want to be able to say they had a winner in the Derby, so they bet the favorite.  And when they play exotics, they use rules of thumb which (I think) lead them to bet favorites too much.  So it is not that I think California Chrome doesn’t have a good chance of being among the top finishers, it is just that from a betting perspective I think he is a sucker bet.

Finally, in keeping with the annual tradition, my prediction for the horse that will finish dead last is Harry’s Holiday.

Good luck!  If you are looking for an easy way to bet the Derby online, check out DerbyJackpot, it is a website started by one of my best friends, and it is the easiest and most entertaining way for the casual bettor to (completely legally) bet on horse racing.