The Kentucky Derby is one of the hardest horse races to bet because it’s unknown territory for the equine competitors. They’ve never run this far and never been part of a field this size. With 20 3-year-olds going 1¼ miles, things can get wild and weird.
But that won’t stop the betting public from trying. It might be a fool’s errand trying to hit the Derby, but it’s also a badge of honor. You have to take a swing, if only for the bragging rights if you somehow get it right.
Accordingly, this is how I would bet $100 in the 150th Run for the Roses on Saturday at Churchill Downs. (Disclaimer: If you unwisely choose to follow my sketchy strategy, that’s a you problem and not a me problem.)
Fierceness is the deserving favorite, and in early wagering, he was bet down from 5–2 to 2–1 as of Thursday afternoon. As is often the case in the gossipy racetrack world, there has been a lot of whispering about whether Fierceness has lost his fastball this week. I’m not buying it.
He’s not physically imposing and isn’t a dazzling morning galloper, but when asked to race, his best is far better than any of his competition. He could, to use a racing term, “bounce” (regress) off his massive Florida Derby effort and still win. Fierceness has the raw speed to get away from early traffic problems as long as he breaks well.
I look for him to be on or near an honest pace before taking command of the race with about five furlongs to go. If the first half mile is run faster than 46 seconds, that will tax the front-runners; if it’s 46 or slower, they’re in good shape. John Velazquez, Fierceness’s excellent jockey, could dictate the early fractions if he gets to the lead without serious pressure.
The win bet: $40 on Fierceness.
Most of the other $60 will go into exotics in search of a bigger payday. I’ll play a $5, three-horse exacta box with Fierceness, Sierra Leone (5–1 as of Thursday afternoon) and Just A Touch (a juicy 14–1). That bet—which calls for two of those three to finish 1-2, in any order—will cost $30.
I’ll also take a swing at a $1 trifecta part wheel, trying to hit the top three finishers. I’ll play Fierceness and Sierra Leone in first with those two, Just A Touch, Catching Freedom (8–1) and Forever Young (8–1) in both the second and third spots. That’s a $24 bet.
I’ll play a $2 Oaks-Derby double, which is picking the winners of both the Kentucky Oaks on Friday and the Derby on Saturday. The wager there will be on Thorpedo Anna in the Oaks and Fierceness in the Derby.
The last four dollars are simply to avoid actively hating myself. I’ll place a $2 win bet on the horse that’s looked good every morning on the track but I don’t have covered otherwise (Santa Anita Derby winner Stronghold at 34–1) and $2 to win on the longest shot on the board (currently Society Man at 59–1). The latter hedge bet is in deference to the Rich Strike fluke-burger win in 2022.
Good luck to everyone. We can all complain about how bad our wagers turn out Saturday night.
