My Annual Kentucky Derby Picks

(Photo: John Athayde)

(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.

David M

So if you where to spend $50 on Derby wagers, how would you bet that money?

caleb b

People love Chitu because of his time, but that is at Sunland - where the dry conditions make for a hard track that the horses can run faster on. Basically, a 1:47.88 at a Sunland track could be a 1:50.50 at Keenland.

Governor Charlie set a track record at Sunland and finished 8th in the Preakness.

I'm thinking Danza might be raced out. He needed to win the Ark Derby just to get in the field and he's raced a lot in the past several weeks. Might be done.

Dances with Fate and Wild Cat Red might be peaking at the right time and they have the post positions to take down the field.

Mike P

Isn't there a well known longshot bias in that bettors prefer to bet on longshots because the bettors derive more utility from the idea of successfully selecting a longshot that ends up winning? Therefore, in regards to horse racing at least, statistically your best bet is to always bet on the favorite?


In last 20 years only 2 horses have won the derby that had not posted a 102 beyer pre-derby. In this years field only 4 have done that, so it seems a pretty good chance winner will come from Cali Chrome, Wicked Strong, Danza, or Chitu.

Caleb B

Okay - after all my reviewing, the longshot that I loved - Wildcat Red, just scratched.

I'm not sure why everyone is hopping of Chrome for Chitu, but I'll stick with Chrome until I hear he's hurt or something.

Last place - Harry's Holiday or Uncle Sigh (not sure why you name a horse out of a blathering 70 year old)

Best value - dance with fate, general A rod, and I'd be okay with putting something on Vacar's in Trouble to hit the board. I know the 1 post, but I could see him coming back and making a charge.


I am not a huge fan of picking favorites but he in the 5th gate which close to the inside but not so close that he should not be bumped and boxed on the start. I also like to bet on jockeys. My favorite jockeys are borel and Velazquez so horse 16 and 19. An interesting favorite of mine is Tapiture his sister just won the Oaks.
If you just want to cash a ticket bet the favorites to show

Paul M.

And let the record show that California "...I think he is a sucker bet." Chrome did, in fact, win the Kentucky Derby. Maybe its just the knowledge of herds?

caleb b

Given that favorites typically only win 33% of the time, I'm not so sure that the herd knows that much when it comes to horse racing.

Ronald Sofia

Steve. I wrote a book but don't have the money to market it. Its called "Disorganized Crime". I spent 30 years in prison and it's a true story about New York, gambling, crime, drugs, the mafia and the witness protection program. I have a manuscript I'd like to send you to review and hopefully give me some advice or direction. I know this is unorthodox but I'm grasping at straws. If you look up "Disorganized Crime" on the internet an author named Douglas Winslow is putting excerpts on his cite. Looking forward to your response and a time I can leisurely explore a rich inner-self.


I know I shouldn't comment because I didn't put my own self out there (BTW, my betting strategy is to pick the Santa Anita Derby winner, so I won this year for once) but dude! This has to be your worst year. Three of your winning picks finished behind the horse you picked for last!


I guess just say your predictions are from a "model" and confidently make some more, even if your batting average is equal to random within the margins, and and all of a sudden you're the "expert" they turn to. Especially in betting, I guess. (I hate the use of that word "gaming" for "betting" and "gambling". George Orwell, wake up!)

Just like the "global warming" models that have no solar cycle input have been so consistently wrong, especially in the past decade and a half of light cooling.

Like the Keynesian economist experts that give advice that has always proven to make us all more poor in the long run and who have gotten us to where we are now.

Ron Keas

Horse #4 will win Kentucky Derby. I'm psychic.


well i guess that "sucker bet" showed you ! lol

Leslie Bair

Sucker bet?


After winning the Preakness and the Derby your statement about Chrome being a "sucker bet" must make you feel like the biggest dumbass going lol!

No whips for horses

After the last race, the winner said that he had a great horse. Then, NO whipping the horse. A lashing to each jockey who hits the horse or no money!

caleb b

I'm not sure what is with the folks that are so excited to point out that Chrome won it. Levitt pointed out that it was the overwhelming favorite.

Thanks for providing your picks. I know i'm one of (maybe) five people that enjoy horse racing that read this blog, but I appreciate you taking the time to write.

Interesting note: The $1 exacta in the Derby paid $340, but the $1 trifecta in the Preakness only paid $40! Ouch.