The $1.5 million, Grade 1 Preakness Stakes at Pimlico follows the Grade 1 Kentucky Derby Presented by Woodford Reserve as the second leg of the Triple Crown, taking place just two weeks after the fabled first jewel of the Triple Crown at Churchill Downs. But what a difference two weeks makes in how horseplayers approach handicapping the two races.

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The Kentucky Derby is typically dissected from every angle, with bettors poring over lots of historical data to identify the most likely winner. In contrast, the Preakness receives considerably less attention from a “trends and angles” perspective, with the historical data instead overshadowed by a single burning question: will the Kentucky Derby winner come back to win the Preakness, setting up a shot at the Triple Crown?

But this doesn’t mean historical data is irrelevant in the Preakness. To the contrary, reviewing the recent history of the Preakness reveals several important trends — including a couple of newly developing ones — that can help us identify the most likely winner.

With this in mind, let’s dig into the data and analyze five tips and trends for handicapping the 2023 Preakness Stakes:

Respect pacesetters and speed horses

As a general rule, it’s wise to bet on horses with tactical speed. Four of the last 15 Preakness winners prevailed in gate-to-wire fashion, including Triple Crown winners American Pharaoh and Justify. Nine others were within four lengths of the lead after the opening half-mile.

In contrast, only two horses in the last 15 years have rallied from the back half of the Preakness field to reach the winner’s circle. Those horses were Rombauer (2021) and Exaggerator (2016), and it’s worth noting the mud-loving Exaggerator caught a deceptively hot pace over a slow, sloppy track he relished.

The Kentucky Derby is no longer the dominant prep race

For decades, the Preakness was dominated by horses exiting the Grade 1 Kentucky Derby two weeks prior. But this trend has been shattered in recent years. Cloud Computing (2017) and Early Voting (2022) exited the Grade 2 Wood Memorial Stakes, Swiss Skydiver (2020) came out of the Grade 1 Kentucky Oaks, and Rombauer (2021) prepped in the Grade 1 Toyota Blue Grass Stakes.

2017 Preakness winner Cloud Computing (Eclipse Sportswire)

In other words, four of the last six Preakness winner skipped the Kentucky Derby. While Derby alumni warrant respect at Pimlico, the past half-dozen years suggest horses who skipped the Derby have a better chance for success in the second jewel of the Triple Crown.

Be careful betting Kentucky Derby winners

Expanding on the above, betting Kentucky Derby winners in the Preakness has been risky business in recent years. Only five of the last 18 editions of the Preakness were won by the Kentucky Derby victor, even though 15 of those Derby winners started in the Preakness. Betting $2 to win on every Kentucky Derby winner would have cost $30 for a return of just $20.40.

That’s not to say you should never bet on a Kentucky Derby winner in the Preakness; standout Derby winners like Big Brown and American Pharoah have made quick work of the Preakness at short prices. But Derby winners aren’t nearly as unbeatable in the Preakness as their short odds tend to imply.

Double-digit longshot winners are increasingly common

Throughout its history, the Preakness has been kind to favorites and short-priced runners. The race has been contested 147 times, but only four winners have ever started at higher than 15-1, with Master Derby’s 23-1 surprise in 1975 standing as the record for a longshot winner.

Oxbow winning Preakness (Eclipse Sportswire)

But does this mean you should avoid betting all longshots in the Preakness? Not at all. Since 2006, we’ve seen a steadily strengthening trend of horses in the low double-digit odds range snatching surprise victories in the Preakness. Indeed, over the past 17 years, horses in the double-digit odds range such as Bernardini (12.90-1), Shackleford (12.60-1), Oxbow (15.40-1), Cloud Computing (13.40-1), Swiss Skydiver (11.70-1), and Rombauer (11.80-1) have won more editions of the Preakness (six) than favorites (five).

The takeaway? Don’t be afraid to bet longshots in the Preakness. It’s increasingly the way to play.

Support proven graded stakes winners

It’s rare for horses unproven against graded stakes company to win the Preakness. In fact, 23 of the last 26 Preakness winners had previously won a graded stakes race, with 17 proving their worth at the Grade 1 level prior to prevailing at Pimlico.

The lone exceptions to the graded stakes trend were Shackleford (2011), Cloud Computing (2017), and Rombauer (2021), though all had finished second at the graded stakes level. Notably, Shackleford came up a head short of victory in the Grade 1 Florida Derby, while Rombauer secured a runner-up finish in the Grade 1 American Pharoah Stakes.

Conclusions

On Friday morning, it was confirmed that Kentucky Derby winner Mage will target the Preakness. By virtue of his success on the first Saturday in May, Mage will be a popular choice in the Preakness betting, but history suggests the stretch-running colt isn’t unbeatable. His running style isn’t ideal for success in the Preakness, and the Kentucky Derby is losing its cachet as the pivotal prep for Pimlico.

First Mission (Matt Wooley/Eclipse Sportswire)

Instead, history suggests we should look for a graded stakes winner with tactical speed who skipped the Kentucky Derby. This conclusion points toward one horse above all others as the most likely Preakness winner: First Mission (NOTE: First Mission was scratched from the Preakness May 19).

Since finishing second in his debut sprinting, First Mission has been unstoppable. He employed pace-tracking tactics to smash the opposition in a 1 1/16-mile maiden special weight race at Fair Grounds by 6 3/4 lengths, then followed up with a similar pace-tracking triumph in the Grade 3 Stonestreet Lexington Stakes at Keeneland. On that occasion, First Mission finished 4 3/4 lengths ahead of Disarm, who came back to run fourth in the Kentucky Derby.

First Mission is lightly raced, but ranks among the most promising 3-year-olds in the country. He won’t be double-digit odds, but bettors who back him in the Preakness should still catch a decent payoff if he upsets Mage.

Good luck, and enjoy the race!