Who was the most surprising Preakness winner of all time?

May 11th, 2022

With the Preakness S. (G1) coming up Saturday, let's look back on Preakness past. Though favorites have had a better record in the Preakness than the Kentucky Derby (G1) or the Belmont S. (G1), the fact that favorites win half the time still means they lose the other half.

Let's revisit some of the biggest Preakness upsets, and then it's up to you. Who was the most surprising Preakness winner of all time?

Bee Bee Bee

He looked like a rising star at Timonium in the summer of 1971. But, after he struggled in Derby preps like the Florida Derby and the Flamingo S., it looked like Bee Bee Bee could not match the best of his class.

He got good again after a return to Maryland, though, and a romping score in the Survivor S. at Pimlico got his connections thinking Preakness.

Sloppy conditions on Preakness day did nothing to dim Bee Bee Bee's love for Maryland. He shot to the front and held off No Le Hace in the lane. He won by 1 1/2 lengths and paid his backers $39.40, in a race where 3-10 favorite Riva Ridge finished a weakening fourth.


The career of 2017 Preakness winner Cloud Computing flashed in the blink of an eye — eight starts, with his only wins in a maiden special weight debut and the Preakness.

But that career feels downright lengthy compared to 1925 winner Coventry.

He never raced at age two. He ran second on debut, then was well beaten in the Wood Memorial, but trainer William Duke had him ready in the Preakness.

The maiden raced off a flying pace set by Backbone, made his run in the lane, and won by four lengths. He paid his backers $45.60, a Preakness record that stood for 50 years. The 22-1 Preakness victory was Coventry's only win in five starts.

Deputed Testamony

Though the Federico Tesio S. currently offers its winner a berth in the Preakness Stakes, it isn't a source of Preakness chalk, and never was.

Yet, that hometown race was part of the route Maryland-bred Deputed Testamony took to the Preakness. He won it in April of 1983, but after he was well beaten in the Blue Grass S. (G2), he returned to the Mid-Atlantic to take his final Preakness prep, the Keystone S.

The Blue Grass was his first graded stakes try, which explains some of the public's hesitance to play him. The entry with Deputed Testamony and stablemate Parfaitement (who finished second in the Wood, though 16th in the Kentucky Derby) went off at 14-1. He saved every inch of ground, began to gain past the three-eighths, drove to the lead midstretch, and won by 2 3/4 lengths, over pacesetter Desert Wine.

Deputed Testamony remained a top horse through his three-year-old season and won the Haskell Invitational H. (G1) that summer.


The most enduring part of Display's legacy is an enigma.

He lends his name to an important juvenile stakes at Woodbine, but Display fell short in both the Grey S. and the Pimlico Futurity at two, and had yet to prove himself among the top of his class come the 1926 Preakness.

As much as people talk about the apocryphal "tight turns of Pimlico" and proclaim that a horse has to have some speed to have any chance in the Preakness, no one told Display that. The 19-1 chance roared through the far turn, took the lead in the lane, and outfinished fellow closer Blondin.

Display rewarded his backers with a $40.70 payout. He also proved to be the most fulfilling kind of longshot — one who stayed well. Display ended his career with 23 wins from 103 starts, with another 52 in-the-money finishes, and raced in stakes company through age six.

Master Derby

Though he was a member of 1970 Kentucky Derby winner Dust Commander's first crop, the public didn't figure he'd become a classic winner, too.

The cool reception to Master Derby was a little perplexing. He had never finished out of the exacta in twelve starts at age two and won five times in eight starts at three. Though the blazed chestnut was supplemented to the Preakness, he was hardly rising from obscurity. He ran in the Kentucky Derby, fourth behind Foolish Pleasure. And yet, the public let him off at 23-1.

Master Derby raced in the pocket, popped out between horses into the far turn, took command past the quarter pole, and even though he drifted out down the lane, Foolish Pleasure couldn't catch him.

Master Derby's $48.80 payoff remains the largest winning price in Preakness history.