Kentucky Derby: How to bet $100

LOUISVILLE, Ky. – There will be the usual pearl clutching in some journalistic corners over media members wagering on the Kentucky Derby on Saturday. Fine. But betting is part and parcel of the sport, and there will be wagers made, and I will be right there with the rest of the riffraff trying to get rich.

Knowing this, the boss asked me to bless the readership with a foolproof plan for betting $100 on the Derby. Thank me later when it turns into thousands and you can take that dream vacation.

The Derby has become more predictable in recent years — the favorite has won five straight, the longest such streak in the race’s 143-year history. But hitting exotic wagers (exacta, trifecta, superfecta) on a 20-horse field remains a daunting task. We will give it a shot, though, with that theoretical Yahoo $100.

(Actual amounts wagered may vary.)

I’ll start with a significant win bet, because saying you picked the Derby winner is both a badge of honor and a decent way to make some cash. The only thing everyone in Louisville will talk about for the 48 hours following the race will be their Derby wagers, and whoever nailed it will have the right to be an insufferable braggart.

Worst among those braggarts are the legion of lucky know-nothings who got the Derby right based on horse names, jockey silks or starting-gate number. If you bet Free Drop Billy at 30-1 because you have an uncle named Billy, and that horse wins, the rest of us hate you.

So, to the windows we go:

I’m betting a theoretical $40 to win on Justify, the morning line favorite at 3-1. He won’t generate a huge payout, but cashing tickets beats betting a wise-guy $40 on a 20-1 horse that finishes eighth. Justify has a 136-year-old curse to overcome, but he’s talented enough to do it.

Kentucky Derby hopeful Justify receives a bath after morning workouts at Churchill Downs on Tuesday. (Reuters)

From there, I’m taking a swing at the superfecta, which requires getting the first, second, third and fourth horses correct. It’s an incredibly difficult Derby bet to hit, but the payouts can be immense. Last year a $1 superfecta ticket paid nearly $76,000, and I think we would all take that, right?

So I will box four horses in a $1 superfecta, a $24 wager. Boxing the horses means that the four can finish in any order, first through fourth. My four-horse box is Justify, Good Magic (12-1), Vino Rosso (12-1) and My Boy Jack (30-1). At least one bomb shot like My Boy Jack tends to hit the board in the Derby and juice up the superfecta price, and I’m taking a flyer on a horse that made a spectacular (but premature) move in the Louisiana Derby before flattening out and finishing third.

Next up, I’ll take a more realistic shot at the exacta, boxing three horses: Justify, Good Magic and Vino Rosso. The bet will be a $4 box, which is $24.

The final $12 will be divided thusly: a $1 trifecta box of the same three horses, which costs $6, and some “saver” bets on horses I like but haven’t otherwise bet on.

I’ll try a $1 trifecta box on Magnum Moon (6-1), Mendelssohn (5-1) and Justify, and another $1 tri box on Justify, Bolt D’Oro (8-1) and Hofburg (20-1).

Those bets are attempted hedges against the inevitable “who’s that?” horse. It’s a Derby tradition to watch the horses entering the stretch and see (at least) one of them who we have forgotten to factor into the handicapping, leading to the collective howl, “Who’s that???”

There’s your Yahoo Kentucky Derby investment advice for 2018. But remember: the surest way to double your money at the racetrack is to fold it in half and put it back in your pocket.

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