Using History to Handicap the 2021 Preakness Stakes

Shackleford denied Animal Kingdom a win in the second jewel of the Triple Crown by taking the 2011 Preakness Stakes by a half-length at Pimlico. (Eclipse Sportswire)

The $1 million Grade 1 Preakness Stakes on May 15 at Pimlico follows the Kentucky Derby Presented by Woodford Reserve as the second leg of the Triple Crown, taking place just two weeks after the fabled showdown under the twin spires at Churchill Downs. But what a difference two weeks makes in how horseplayers approach handicapping the two races.

The Kentucky Derby is typically dissected from every angle, with bettors pouring over tons 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, the race tends to produce similar results year after year, and reviewing the recent history of the Preakness can help guide us toward logical contenders.

With this in mind, let’s dig into the data and review five valuable tips and trends for handicapping the 2021 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 12 Preakness winners prevailed in gate-to-wire fashion, including Triple Crown winners American Pharoah and Justify. Six others were racing within 3 1/2 lengths of the lead after the opening half-mile.

In contrast, only one horse in the last 12 years has rallied from the back half of the Preakness field to reach the winner’s circle. That one horse was the mud-loving Exaggerator, who benefited from chasing a fast pace over a sloppy, tiring track to close from eighth place and win easily in 2016.



Position after first 1/2 mile

½-mile & ¾-mile times


Swiss Skydiver

5th by 3 lengths (11 starters)

47.65, 1:11.24 (fast)


War of Will

4th by 3.5 lengths (13 starters)

46.16, 1:10.56 (fast)



1st by a head (8 starters)

47.19, 1:11.42 (sloppy)


Cloud Computing

3rd by 3 lengths (10 starters)

46.81, 1:11.00 (fast)



8th by 6.5 lengths (11 starters)

46.56, 1:11.97 (sloppy)


American Pharoah

1st by 2.5 lengths (8 starters)

46.49, 1:11.42 (sloppy)


California Chrome

3rd by 2 lengths (10 starters)

46.85, 1:11.06 (fast)



1st by 2 lengths (9 starters)

48.60, 1:13.26 (fast)


I’ll Have Another

4th by 3.5 lengths (11 starters)

47.68, 1:11.72 (fast)



2nd by 0.5 lengths (14 starters)

46.87, 1:12.01 (fast)


Lookin At Lucky

5th by 5 lengths (12 starters)

46.47, 1:11.22 (fast)


Rachel Alexandra

1st by a head (13 starters)

46.71, 1:11.01 (fast)

Favor horses exiting the Kentucky Derby and Kentucky Oaks

Swiss Skydiver (inside) defeats Authentic in 2020. (Eclipse Sportswire)

Over the last 20 years, horses exiting the Kentucky Derby have dominated the Preakness, visiting the winner’s circle 16 times. Two others (the fillies Rachel Alexandra and Swiss Skydiver) used the Kentucky Oaks as their springboard to glory at Pimlico, leaving Bernardini (coming off a win in the Withers Stakes at Aqueduct) and Cloud Computing (exiting a third in the Wood Memorial at Aqueduct) as the only Preakness winners since 2001 who didn’t prep in the Derby or Oaks.

Bet Kentucky Derby winners trained by Bob Baffert

Hall of Fame trainer Bob Baffert has won the Preakness a record seven times. All seven of his winners came out of the Kentucky Derby, including five who prevailed in the “run for the roses.”

To put it another way, Baffert’s first five Kentucky Derby winners all came back to win the Preakness. The only Baffert Derby winner who failed to claim victory at Pimlico was Authentic, who finished second by a neck in 2020. Notably, there were extenuating circumstances – the 2020 Preakness was held in October due to COVID-19, and the race took place four weeks after the Kentucky Derby rather than the typical two weeks.

Avoid playing major longshots

It’s not uncommon for mid-range longshots to reach the Preakness winner’s circle. In the last 15 years, Bernardini (2006), Shackleford (2011), Oxbow (2013), and Cloud Computing (2017) have all prevailed at odds between 12-1 and 15-1.

But it’s a testament to the generally predictable nature of the Preakness that these four upset winners rank among the 11 highest-priced winners in Preakness history. Although the race has been contested 145 times, 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.

Again, there’s no reason to avoid mid-range longshots; double-digit winners have been just as common as winning favorites over the last 15 years, with each group claiming five victories. But history suggests bettors should hesitate before supporting horses at higher than 15-1 in the betting.

Support proven graded stakes winners

It’s rare for horses unproven against graded stakes company to win the Preakness. In fact, 18 of the last 20 Preakness winners had previously won a graded stakes, with 14 proving their worth at the Grade 1 level prior to prevailing at Pimlico.

The lone exceptions to the graded stakes trend were Shackleford (2011) and Cloud Computing (2017), though both had placed second at the graded stakes level, with Shackleford most notably coming up a head short of victory in the Grade 1 Florida Derby.


Kentucky Derby winner Medina Spirit. (Eclipse Sportswire)

The Preakness field is still coming into focus, but one contender who looks formidable from a historical perspective is Medina Spirit. Trained by Bob Baffert, the dark bay colt was a surprise winner of the Kentucky Derby, leading all the way to spring a 12.10-1 upset. But you can bet he won’t be a longshot at Pimlico – with his front-running speed and proven form against Grade 1 company, Medina Spirit is a perfect match for the historical profile of a Preakness winner. All signs suggest he’ll be very tough to defeat.

Medina Spirit will be joined in the Preakness by fellow Kentucky Derby starters Midnight Bourbon (sixth) and Keepmeinmind (seventh). Both are proven graded stakes winners, with Midnight Bourbon looming as a particularly strong contender from a historical standpoint. A troubled start forced Midnight Bourbon to rally from mid-pack in the Kentucky Derby, but it’s more common for the son of Tiznow to race up and on the pace, as he did win wiring the Grade 3 Lecomte Stakes during the winter. A clean break against a smaller field in the Preakness figures to place Midnight Bourbon in the hunt for a strong finish at what should be good odds.

A wildcard in the Preakness field is Bob Baffert’s Concert Tour, winner of the Grade 2 Rebel Stakes and third in the Grade 1 Arkansas Derby. The son of Street Sense is clearly a talented prospect, and he’ll be a short price at Pimlico. But the fact he didn’t contest the Kentucky Derby is a meaningful question mark from a historical standpoint.

Good luck, and enjoy the race!

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