How to bet $100 on the Preakness Stakes

After heroically padding the wallets of the readership with Kentucky Derby winnings two weeks ago – nearly tripling your investment – the directive came down from my benevolent Yahoo Sports overlords this week:

Do it again. Give us another $100 worth of wagers on the Preakness.

If called, I will serve. But with the following caveat: this is a terrible race to bet.

It will be very hard to cash big tickets on the Preakness within the confines of a $100 bankroll. The favorite, undefeated Derby winner Justify, opens at odds of 1-2. If you believe he can be beaten, and bet accordingly, you can make some money if it comes in that way. I do not believe Justify can be beaten – best horse plus best trainer in Bob Baffert, who has won this race six times including after each of his previous Derby victories – which limits the options for lucrative Preakness wagers.

The best play might simply be taking the $100 and putting it on Justify to win. But the payout would only be $150 at his current 1-2 odds, and it would make for a pretty short column. So let’s scrap the win bet and try Plan B.

The big payouts might be in what’s referred to as “horizontal” wagers – Pick Threes, Pick Fours, Pick Fives and Pick Sixes. In those bets, you’re trying to pick winners in multiple consecutive Pimlico races, with Justify the lone selection (“singled,” in the nomenclature) in the Preakness. But we’re skipping those as well – the bets would have to be made as the action is unfolding Saturday, while assessing track conditions in what’s expected to be another very soggy day of racing. (The Bleakness, as it were.)

And we’re trying to keep this relatively simple anyway, so forget the horizontals. Let’s stick to the Preakness itself.

I’d start with a souvenir $2 win ticket on Justify. If he wins this race and goes on to take the Belmont on June 9, you’ve got a Triple Crown keepsake. Beyond that, this is a time to play the exotic bets, with heavy reliance on Justify as the dominant horse against a thin and likely overmatched field.

I had the Derby exacta: Justify and Good Magic 1-2. I’ll play the same exacta this time, but I’m upping the bet from a $2 box (which means they can finish in either order) to a $10 box. That will cost $20. With Good Magic the second choice at a paltry 3-1, it will not pay a lot. But it would be a start on making some money.

(The nagging concern: is Good Magic a tired horse coming out of Louisville? A photo that made the rounds this week showed the colt’s ribs rather prominently, which led to concerns Good Magic has lost weight after the slog through the mud at Churchill Downs. Justify ran every bit as far and a bit faster, but he had an easy trip on the front end of the pack. Good Magic didn’t have it quite as smooth.)

After that I’ll play a $1 trifecta, keying Justify on top over all the rest of the eight-horse field in both the second and third spots. (Justify/all/all, in wagering parlance). That’s a $42 bet, and obviously the payout is enhanced if something unforeseen happens and some longer shots hit the board – which has been known to happen in recent Preakness races.

In 2015, Tale of Verve rallied to finish second at 28-1. In 2016, Cherry Wine was the runner-up at 17-1. And last year Senior Investment finished third at 31-1 (with Cloud Computing the upset winner at 13-1). If a similar bomb shot hits the board this year – especially behind a Justify/Good Magic exacta, which we would have as well – the trifecta gets better.

From there, I’ll spend $24 on a superfecta box: Justify, Good Magic, Quip (12-1) and Lone Sailor (15-1). (There are smarter wheels to play here, but I’m trying to keep it relatively simple.) Superfectas are hard to hit, especially if you limit yourself to four horses, but if this comes in there will be money made. While it would be nice to have these four to come in with Justify and Good Magic on top – which would mean we’ve hit the exacta, trifecta and superfecta – the price on the super would be much higher with a Quip-Lone Sailor top two and the others in third and fourth.

With the remaining $12, we might as well take a shot at a trifecta in which things go off the rails and Justify runs out of the top three. I’d box Good Magic, Quip and Lone Sailor in a $2 tri.

Unlike two weeks ago, when many of you were ready to name your next child Pat, this isn’t much of a get-rich-quick race. Prepare accordingly. The best thing to do might be sitting on your wallet and just watching this one for fun.

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