How Kentucky Derby longshot winners finish in the Preakness

May 19th, 2022

Massive underdog Rich Strike, who won the 148th running of the Kentucky Derby (G1) at 80-1 odds, is now set to compete in the Preakness S. (G1), the second leg of the Triple Crown, at Pimlico on May 21.

While virtually no racing analyst or expert pegged Rich Strike as a serious threat in the Run for the Roses, the Eric Reed pupil will have all eyes on him in Baltimore against a potential field of 14.

Rich Strike isn’t the first mega-longshot to run in the Preakness off a shocking win in the Kentucky Derby. Below we look at 10 of the longest shots to win the Derby and how they fared in the second jewel of the Triple Crown.

1. Donerail

Year of Kentucky Derby win: 1913
Kentucky Derby odds: 91-1
Preakness finish: Did not start

Bred, owned, and trained by Thomas P. Hayes, Donerail became the longest shot to win the Kentucky Derby in 1913, during the 39th Run for the Roses, six years before Sir Barton won the Derby, Preakness, and Belmont S. (G1) in the same year.

The term “Triple Crown,” as a reference to the Derby, Preakness, and Belmont, can be traced as far back as 1923 but did not become commonly recognized until 1930, when Charles Hatton of the Daily Racing Form used the phrase to describe Gallant Fox’s collective triumph in all three races.

Thus, Donerail's victory came before the Triple Crown became prominent, and he didn't race in the Preakness or Belmont. The champion racehorse also won the 1913 Canadian Sportsman’s Handicap and 1914 Hamilton Cup, retiring with a 62 10-11-10 record and $15,156 in career earnings.

2. Country House

Year of Kentucky Derby win: 2019
Kentucky Derby odds: 65-1
Preakness finish: Did not start

At 65-1 odds, Country House crossed the wire second, 1 3/4 lengths behind Maximum Security in the 2019 Kentucky Derby, but he was awarded first after Maximum Security was disqualified for interference.

Country House withdrew from the Preakness after trainer Bill Mott detected a virus, leaving the Preakness field without that year’s Kentucky Derby winner for the first time since 1996, and he eventually retired without racing again.

Maximum Security’s connections opted to forgo the Preakness, while Code of Honor and Tacitus, second and third in the Derby, skipped as well. War of Will, the horse Maximum Security initially bumped in the Derby to cause interference, won the second leg of the Triple Crown after being elevated to seventh in the Derby.

3. Mine That Bird

Year of Kentucky Derby win: 2009
Kentucky Derby odds: 50-1
Preakness finish: Second

With jockey Calvin Borel in the silks, Mine That Bird stunned more than 153,000 Churchill Downs attendees under the Twin Spires when he roared to a 6 3/4-length victory in the fastest two minutes in sports.

In the 2009 Preakness, Borel hopped off Mine That Bird to pick up the mount on Kentucky Oaks (G1) winner Rachel Alexandra and guided the filly to a one-length win over the Derby victor, who was ridden by Hall of Fame jockey Mike E. Smith in the Preakness.

4. Giacomo

Year of Kentucky Derby win: 2005
Kentucky Derby odds: 50-1
Preakness finish: Third

Not only did Giacomo’s Derby win result in what was then the second highest payout in the race’s history, but the second-place finisher, Closing Argument, was a massive longshot as well, completing a $9,814.80 exacta.

In Giacomo’s Preakness run, he was bet down as the 6-1 third choice, behind post-time favorite Afleet Alex and the Nick Zito trainee High Fly, and wound up third beneath Mike Smith. Afleet Alex courageously won going away over Scrappy T.

5. Gallahadion

Year of Kentucky Derby win: 1940
Kentucky Derby odds: 35-1
Preakness finish: Third

A son of leading North American sire Sir Gallahad III, Gallahadion triumphed in the 1940 Kentucky Derby by 1 1/2 lengths over heavy favorite Bimelech, the 1939 U.S. champion 2-year-old colt who was making his third start in eight days.

Bimelech got his revenge by winning both the Preakness and Belmont, while Gallahadion finished third in the race at Pimlico and was unplaced in the 1 1/2-mile Belmont.

The longshot Kentucky Derby champ owned by Ethel V. Mars' Milky Way Farm Stable finished with a 36 6-6-4 lifetime record.

6. Apollo

Year of Kentucky Derby win: 1882
Kentucky Derby odds:
Preakness finish:
Did not start

Before Justify became the second horse to accomplish the feat in 2018, Apollo was long known as the first and only horse to win the Derby without racing at age two.

In 1882, back when the Derby covered 1 1/2 miles, the chestnut entered the event having broken his maiden just 20 days earlier in the Cottrill Stakes at the same distance. In the eighth running of the Kentucky Derby, he bested 4-5 favorite Runnymede, a multiple stakes winner, by a half-length.

The race rivals met six days later in the Clark Stakes, with Runnymeade securing the win, while Apollo came in third.

Owned and trained by Green B. Morris, Apollo won 10 of his 21 starts as a three-year-old and finished out of the money once that season, but he did not start in the Preakness. The winner of the Pimlico event was Vanguard in 1882.

7. Charismatic

Year of Kentucky Derby win: 1999
Kentucky Derby odds:
Preakness finish:

After losing his first five starts as a two-year-old, trainer D. Wayne Lukas entered Charismatic into a maiden claiming race in November 1998. The colt escaped the win unclaimed, but he kicked off another losing streak in his next race.

Owner Bob Lewis had practically given up on the horse, but Charismatic flashed his potential in a record-setting finish in the Lexington S. (G2), his first stakes victory, which also earned him a spot in the 125th running of the Kentucky Derby.

As a 31-1 longshot in a field of 19, Charismatic withstood a late charge from Blue Grass S. (G1) champ Menifee to win the Derby by a head. He again outbid Menifee, this time by 1 1/2 lengths in the 1 3/16-mile Preakness on May 15.

Charismatic went off as the 2-1 favorite in the Belmont on June 5 but was denied a Triple Crown title when he suddenly slowed down after taking the lead at the three-sixteenths pole, finishing third behind winner Lemon Drop Kid.

Rider Chris Antley sensed something was off and eased Charismatic in the final furlong. The jockey dismounted from the horse once he crossed the finish line and held up the colt's front leg, which had been fractured in multiple places.

Charismatic never raced again but still won the Eclipse Award for Horse of the Year and champion three-year-old male.

8. Proud Clarion

Year of Kentucky Derby win: 1967
Kentucky Derby odds:
Preakness finish:

With then the third-fastest winning time (2:00.60) in the Derby, Proud Clarion crossed the wire first with jockey Bobby Ussery in the 93rd Run for the Roses.

Heavy favorite Damascus placed third but bounced back to win the Preakness with Hall of Fame rider Bill Shoemaker, while Proud Clarion came in third, then placed fourth to Damascus in the third leg of the Triple Crown.

With just six wins in 25 career starts, Proud Clarion's only other major win came in the Roamer H. at Aqueduct, where he set a new track record of 1:55 flat at 1 3/16 miles.

9. Exterminator

Year of Kentucky Derby win: 1918
Kentucky Derby odds:
Preakness finish:
Did not start

In his first start as a three-year-old, Exterminator defied the odds to beat Escoba by a length on a muddy track in the 44th running of the Kentucky Derby, the year before Sir Barton became the first horse to win the Triple Crown.

Owner Willis Sharpe Kilmer had bought Exterminator to help train champion 2-year-old colt Sun Briar and thought little of the chestnut he nicknamed "that truck horse" before his iconic win at Churchill. When Sun Briar developed ringbone, Kilmer entered Exterminator into the Derby upon convincing by Matt Winn, then the president of Churchill Downs.

Exterminator went on to become a successful turf runner and was voted U.S. Champion Older Male Horse in 1920, 1921, and 1922.

He did not enter the 1918 Preakness, which was split into two divisions that year. War Cloud, the Derby favorite, won the first division, and Jack Hare Jr. won the second.

10. Thunder Gulch

Year of Kentucky Derby win: 1995
Kentucky Derby odds:
Preakness finish:

Breaking out of Post 16, Thunder Gulch won the 121st running of the Kentucky Derby for trainer D. Wayne Lukas, who entered three horses in the 1995 field.

The Mr. Prospector grandson came home third to stablemate Timber Country in the Preakness but secured the third leg of the Triple Crown with a two-length victory in the Belmont, which gave Lukas a Triple Crown title, but with two different horses winning legs of the classic series in one season.

Thunder Gulch went on to win the prestigious Travers S. (G1), becoming only the fourth horse to sweep the Kentucky Derby, Belmont, and Travers.