Tips for Betting the 145th Kentucky Derby

ESPN senior researcher Chris “The Bear” Fallica shares a few historical trends to keep in mind before this year’s Run for the Roses

Photo: Andrew Hyslop

Photo: ESPN images

Chris Fallica.

There are plenty of ways to prepare for the Kentucky Derby this Saturday. Find a hat. Whip up some Benedictine spread. Learn to mix a julep. And know how you’re going to bet. We at G&G are checking the odds and brushing up on Betting 101, but we also went to an expert for some advice. Enter Chris Fallica, a senior researcher at ESPN (and a familiar face to any College GameDay fan). We asked “The Bear” to share his tips on betting the Derby, and he came back with a few historical trends—plus one Derby Day gambling strategy—to keep in mind as you pick your ponies.


Don’t bet on a horse to win from Post 1, 2, or 3.

“No horse has won the Kentucky Derby from post one or two in thirty-three years (Ferdinand, 1986), and it’s been twenty-one years since a horse has won from post one, two or three (Real Quiet, 1998). In a twenty-horse field, the horses on the inside rarely work out a good trip and encounter traffic problems or are compromised by the rail.”


Don’t throw the favorite out.

“From 1980 to 1999, not a single favorite won the Derby. But that bad fortune has changed. Derby favorites have now won the race six straight years.”


Take a pass on the third betting choice.

“The third choice hasn’t won the Derby since Strike the Gold in 1991. Last year, Mendelssohn was a trendy pick as the third choice in the race—and finished last!”


The Wood Memorial winner may not be your best bet.

“Historically a key prep for the Kentucky Derby, the Wood Memorial Stakes has not produced a top-three finisher in the Derby since 2003, when Empire Maker finished second to Funny Cide. In the last three years, the Wood winner has finished ninth (Vino Rosso last year), tenth (Irish War Cry in 2017) and fourteenth (Outwork in 2016). Tacitus won the 2019 Wood Memorial.”


That Bob Baffert guy is a pretty good trainer.

“Baffert has won the Kentucky Derby five times, including last year with Justify. His next win will match Ben Jones for the most wins by a trainer in Derby history with six. So be sure to give the Baffert runners an extra look.”


Steve Asmussen is jinxed at the Derby.

“Well, we hope that’s not the case, but Asmussen has zero wins from nineteen Derby starters. That’s the most Derby starters for a trainer without a win in Derby history.”


Betting the Derby should be fun!

“A fun way for a big group at the track to enjoy the day and not bet a whole lot is to have everyone throw in a few bucks and start a rolling show pool. What is that, you ask? Each race, people take turns picking one horse in the race to show, meaning the horse has to finish in the top three. If you win, each race you continue rolling your entire pool of winnings onto another horse to show. If you lose, you simply start over. And if you don’t lose, well, it can be a pretty good return on investment and keep you interested throughout the great day of racing.”