Whenever someone asks “why should I bet on horse racing?” … a great answer is the potential for massive returns on a small investment, and the trifecta is a wager that offers this opportunity, especially in the Kentucky Derby Presented by Woodford Reserve.

For the uninitiated, a trifecta is simply the selection of the first three finishers in a horse race. You can bet a straight trifecta in which horses “A,” “B,” and “C” finish in exact A-B-C order, first, second, and third. You can also bet a “trifecta box,” which allows you to cash your ticket if those same three horses finish first thru third in any order. So, C-B-A would still win, C-A-B would be a winner as would B-C-A, and so on.

The highest trifecta payout in Kentucky Derby history came exactly 20 years ago in 2005 when longshots Giacomo and Closing Argument finished first and second, followed by one of the race favorites Afleet Alex. It paid $133,134.80. Yes, $133,134.80 for a $2 bet.

My Favorite Derby Trifecta

My favorite Kentucky Derby trifecta story happened all the way back in 1998. I went to the track at Belmont Park that day and had the intention of betting Bob Baffert’s Indian Charlie and boxing him in exactas with Victory Gallop. I’ll never forget the ABC television coverage of the walkover that day, which focused on Baffert because Indian Charlie was favored. Every time the camera turned to Baffert, he put his index finger up to his lips in a “shushing” motion. He didn’t say a word, just “shushhhh” with his finger to his lips. Baffert’s "other" horse in that Derby was Real Quiet, a horse I’d overlooked until that moment. I rushed to the windows to bet trifecta boxes using Real Quiet in addition to my other two horses. Baffert knew it all along. The trifecta came out Real Quiet – Victory Gallop – Indian Charlie. It paid $1,221 for a $2 bet.

My 2025 Derby Trifecta

To me, the most impressive horse this spring has been Journalism, and even as the favorite he will be my top selection unless he draws the rail. I’m rooting for Sandman, who I believe is loaded with talent. If he can put it all together on Derby day, he should be the best of the closers. In my opinion, most traditional handicapping goes out the window when it comes to a 20-horse field in the Kentucky Derby. After Forever Young’s rousing third-place finish last year, I’m intrigued by this year’s top Japanese invader Luxor Café, so he will definitely be on all of my tickets. Rounding out my trifectas will be my pick for the cutest Derby contender, Tiztastic, the winner of the Twinspires.com Louisiana Derby at the distance of 1 3/16 miles.

My Bets

Let’s face it, hitting the Kentucky Derby trifecta is tough to do and I don’t suggest pouring a ton of money in to chase it. The trifecta in the Kentucky Derby is meant to give you a chance to bet a little to win a lot, so you don’t need to go crazy with big denominations in order to get a big payoff. I will go for it by betting a total of $30 in trifectas in order to keep it simple, as follows:

There is some overlap with my trifecta box and trifecta key wagers. I can win both bets if Journalism wins the race. My trifecta box gives me an opportunity to cash a bet even if my top pick Journalism loses.

$1 Trifecta Box ($24 total bet)

Four-horse $1 trifecta box (requires any three of these four horses to finish first, second, and third in any order): Journalism, Luxor Café, Sandman, and Tiztastic ($24 total bet)

$1 Trifecta Key ($6 total bet)

Journalism will be my key horse to win and will be my key horse to win on top of three horses underneath: Luxor Cafe, Sandman, and Tiztastic. This bet wins if Journalism wins and any of two of these three horses finish in the second and third slots.

$1 Trifecta key: Journalism (First) with Luxor Café, Sandman, and Tiztastic (Second) with Luxor Café, Sandman, and Tiztastic (Third) ($6 total bet)