How to bet the Preakness after the mess at the Kentucky Derby

From a storyline perspective, the Preakness is a near-total bust. Both Kentucky Derby winners are out — Maximum Security, who crossed the wire first but was disqualified, and replacement winner Country House. To quote Apollo Creed, ain't gonna be no rematch.

Those two have company on the no-show list. Code of Honor, elevated to second in the Derby, is sitting this one out as well. So is third-place finisher Tacitus. Baltimore hasn’t been snubbed like this since the Colts left town.

The last time the Preakness contained none of the Derby’s top three finishers was 1951. That was so long ago, “separate but equal” was still the law of the land in terms of segregation. And Pimlico Race Course hadn’t even become an embarrassing dump of a facility yet.

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But for all the bleakness of this Preakness, it’s not a terrible betting race — in fact, it looks more lucrative on paper than most recent editions. There is money to be won Saturday, so let’s attempt to do so. Here’s how to bet $100 on the Preakness and emerge a millionaire*:

(*You will not actually be a millionaire, even if every bet hits.)

Only once in the last decade has a horse that didn’t run in the Derby won the Preakness — that was Cloud Computing, in 2017. But as noted above, this is a pretty uninspiring group of Derby runners shipping to Pimlico.

Improbable, trained by six-time Preakness winner Bob Baffert, is the favorite at 5-2 — fairly plump odds for this race, since the Derby winner is often heavily favored in the second leg of the Triple Crown. Improbable will be used in exactas and trifectas, but he’s hardly unbeatable. (In fact, he’s been beaten in all three of his starts as a 3-year-old.)

Trained by Bob Baffert, Improbable is the favorite to win the Preakness on Saturday. (AP)
Trained by Bob Baffert, Improbable is the favorite to win the Preakness on Saturday. (AP)

Same goes for morning-line second choice War of Will (4-1 odds). His chances in the Derby were compromised by the fateful near-collision with Maximum Security on the far turn, but even with a clean shot this is a horse that doesn’t look like he wants to go much farther than a mile — and the Preakness is 1 3/16 miles. Further complicating War of Will’s chances is the fact that he drew the No. 1 post, just as he did in the Derby, greatly increasing the chances of more traffic problems.

Thus I’m going to key my wagering around a “new shooter,” as the racing term goes. That’s Alwaysmining (8-1), a Maryland-bred, Maryland-based horse on a six-race winning streak, most recently an 11½-length romp in the Federico Tesio Stakes in April. Alwaysmining’s path through a series of races at nearby Laurel Park has pointed toward the Preakness, whereas Improbable and War of Will are trying to maintain form after pointing toward the Derby.

So let’s start with a $20 win bet on Alwaysmining. The competition will be tougher than any he has faced yet, and this is certainly the biggest race ever contested by trainer Kelly Rubley and jockey Daniel Centeno. But if the humans don’t screw it up, the horse appears to be good enough.

Then let’s box Alwaysmining with Improbable and War of Will in a $10 exacta. That’s a $60 bet that could pay pretty well, if the morning-line odds hold until race time. (Not a given.)

With $20 left to play with, let’s do a $2 trifecta box on the same three horses (a $12 bet) and a $1 trifecta box on Alwaysmining, Improbable and 6-1 Anothertwistafate (a $6 bet). Anothertwistafate is coming off a second-place finish in the Lexington Stakes after being boxed in for much of that race, and a jockey change to Jose Ortiz could pay dividends.

That leaves $2. Let’s just suppose that the 2019 Kentucky Derby was completely cursed in every respect and toss out all four Derby runners — Improbable, War of Will, Win Win Win and Bodexpress. Take that last two bucks and bet a straight new shooter trifecta: Alwaysmining, Anothertwistafate and Owendale (10-1).

Go to the windows with confidence, and enjoy your newfound wealth.

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