The appeal of betting on horse racing, for me at least, is summed up in the axiom, “bet a little to win a lot.” That requires finding longshots worthy of making a win bet on and also structuring what are called “exotic bets” such as the exacta and trifecta to ensure a hefty payout.

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 through 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.

If you place a winning trifecta bet in the most popular horse racing in the world, the Kentucky Derby, more often than not you’re going to make a good profit – and in some years when the longshots come in, it gets really crazy. 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. Take a guess at what a $2 trifecta with Giacomo-Closing Argument-Afleet Alex paid. It paid $133,134.80. Yes, $133,134.80 for a $2 bet.

A Derby Trifecta Tale of Woe

When asked to contribute to this ABR group assignment, I meekly protested, “But what if the writer hasn’t hit a Derby trifecta?” (My absence was not excused.) Fact is, I haven’t hit one. For a moment, I seemed to recall connecting on the 2007 Derby trifecta that included what turned out to be three great horses – Street Sense, Hard Spun, and Curlin – but after looking back at the chart, I didn’t have it. There have been a few near-misses, usually involving a horse that I had placed in the third slot but not the second, finishing second (Two Phil’s in 2023 and Bodemeister in 2012 come to mind). And then there have been more than a few complete misses … the less said about those, the better.

My 2025 Derby Trifecta

In the Kentucky Derby, I usually swing big on a trifecta using the smallest denomination (50 cents) and adding a bunch of horses in the third leg. The horses I use in the first slot are my best win bets and usually have a stamina pedigree edge on the rest of the field. This year, those horses are (in alphabetical order) Journalism, Luxor Café, Sandman, and Sovereignty. In the second slot, I’ll toss Rodriguez in with those four because I think he’s the best of the speed horses in this year’s Derby and could hang on for a while in the stretch after leading at the quarter pole. And then I’ll spread it a little bit more in the third leg and add the following runners that could be passing tired horses in the stretch – Burnham Square, Final Gambit, and Tiztastic.

My Bet

50-cent trifecta part wheel:

Journalism, Luxor Café, Sandman, and Sovereignty with Journalism, Luxor Café, Rodriguez, Sandman, and Sovereignty, with Burnham Square, Final Gambit, Journalism, Luxor Café, Rodriguez, Sandman, Sovereignty, and Tiztastic.

Total cost: $48.

Depending on how much of a bankroll I have by the time the Derby post time approaches, I’ll consider boxing those top four horses in a trifecta as well, for either 50 cents ($12) or $1 ($24).

Use ABR’s Gambling Calculator to create your own ticket.