Pimlico is different. It’s grittier than Churchill Downs and lacks the massive, sweeping scale of Belmont Park. But for anyone who follows the list of Preakness Winners, you know that the "Middle Jewel" of the Triple Crown is where the real chaos—and the real legends—happen.
Honestly, the Kentucky Derby gets the roses and the hats, but the Preakness Stakes is often where we find out if a horse actually has the heart to be a champion. Since 1873, this race has been a graveyard for some favorites and a springboard for others. It’s shorter than the Derby at 1 3/16 miles. It’s faster. And it’s a lot more intimate.
The Modern Era: Who Won the Most Recent Preakness?
If you haven't been keeping track of the last few years, the winners' circle has seen a wild mix of dominant favorites and stunning upsets.
In 2025, it was all about Journalism. Ridden by Umberto Rispoli and trained by Michael McCarthy, Journalism wasn't just a horse with a clever name—he was a powerhouse that clocked in at 1:55.47. He held off Gosger and Sandman to take home the bulk of that $2 million purse.
Before him, 2024 gave us a massive feel-good story with Seize the Grey. Trained by the legendary D. Wayne Lukas (who seems to have found the fountain of youth), Seize the Grey won it for the "people," being owned by the MyRacehorse micro-share group. It’s not every day thousands of regular folks can say they technically own a Preakness winner.
Here is a quick look at the winners from the 2020s so far:
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- 2025: Journalism
- 2024: Seize the Grey
- 2023: National Treasure
- 2022: Early Voting
- 2021: Rombauer
- 2020: Swiss Skydiver (A rare filly win!)
Swiss Skydiver’s 2020 victory was something else. Because of the pandemic, the race was moved to October, and she faced off against the Derby winner Authentic in a stretch duel that people still talk about. She became one of only six fillies to ever win the race.
The Horses That Actually Swept the Triple Crown
You can't talk about the list of Preakness Winners without highlighting the elite 13. These are the ones who took the Derby, then Pimlico, then the "Test of the Champion" at Belmont.
The most famous, obviously, is Secretariat (1973). For decades, there was actually a controversy about his time. It was originally recorded as 1:54 2/5, but after a forensic review of the tapes years later, it was corrected to 1:53.00 flat. That remains the stakes record. No horse has ever run it faster.
Then you’ve got the more recent legends. American Pharoah (2015) broke a 37-year drought, winning the Preakness in a literal monsoon. The track was a lake, and he just floated over it. Three years later, Justify (2018) did the same, emerging from a thick fog at Pimlico to keep his undefeated streak alive.
The All-Time Triple Crown Winners
- Sir Barton (1919)
- Gallant Fox (1930)
- Omaha (1935)
- War Admiral (1937)
- Whirlaway (1941)
- Count Fleet (1943)
- Assault (1946)
- Citation (1948)
- Secretariat (1973)
- Seattle Slew (1977)
- Affirmed (1978)
- American Pharoah (2015)
- Justify (2018)
The Forgotten History and Weird Records
Most people think the Preakness has always been at Pimlico. Mostly true, but not entirely. Between 1890 and 1908, the race actually moved to New York—first to Morris Park and then Gravesend. They call those the "Lost Preaknesses."
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And then there’s the distance. It wasn't always 1 3/16 miles. It’s been as long as 1 1/2 miles (the first race in 1873) and as short as a mile. They finally settled on the current distance in 1925.
Smarty Jones (2004) holds the record for the biggest blowout. He won by 11 1/2 lengths. It wasn't even a race; it was a glorified morning gallop. On the flip side, Sunday Silence (1989) beat Easy Goer by a nose in what many consider the greatest horse race ever run. Two titans, side by side, refuse to blink.
Why the "C" and "S" Names Matter
This sounds like total superstition, but the stats are weird. If you’re looking at the list of Preakness Winners, horses with names starting with "C" or "S" dominate the history books.
As of 2025, horses starting with "C" have 17 wins (think Cloud Computing, Curlin, Citation). Horses starting with "S" are right behind them with 16 (think Secretariat, Swiss Skydiver, Seize the Grey). If you're a betting person, the alphabet might actually be your best friend at Pimlico.
Training the Champions: Baffert and Lukas
If you want to win at Pimlico, you usually hire one of two guys. Bob Baffert and D. Wayne Lukas are the undisputed kings of this race.
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Baffert currently holds the record for the most trainer wins with eight, most recently with National Treasure in 2023. Lukas isn't far behind. His win with Seize the Grey in 2024 was his seventh. These guys understand the "quick turnaround"—the grueling two-week gap between the Derby and the Preakness that breaks most horses.
Real Talk: Why Some Derby Winners Skip It
In recent years, we've seen a shift. In 2022, the Derby winner Rich Strike skipped the Preakness entirely. Why? Because the modern thoroughbred is bred for speed, not necessarily the stamina to run three massive races in five weeks.
This creates a different kind of Preakness. Sometimes, the "new shooters"—horses that didn't run in the Derby—come in fresh and just blow the field away. That’s exactly what Early Voting did in 2022. He sat out the Derby specifically to target the Preakness, and it paid off.
Actionable Insights for Racing Fans
If you're studying the list of Preakness Winners to understand how to handicap the next race, keep these expert-level nuances in mind:
- Look for "New Shooters": Don't just bet the Derby winner. Fresh horses that skipped Churchill Downs have a massive statistical advantage because they aren't tired.
- The Speed Bias: Pimlico’s track surface often favors horses that are on or near the lead. It is notoriously difficult to close from way back on this dirt.
- Watch the Weather: Pimlico can turn into a "soupy" mess quickly. Some horses, like Exaggerator (2016) or American Pharoah, specifically excel in the mud.
- Check the Trainer: If Baffert or Lukas has a horse in the field, ignore them at your own peril. They know exactly how to peak a horse for this specific 1 3/16-mile distance.
To truly appreciate the Preakness, you have to look past the Maryland crab cakes and the infield party. Look at the names on that trophy—the Woodlawn Vase. It’s a list of the toughest, fastest, and most resilient animals to ever step onto a track. Whether it's a Triple Crown winner or a blue-collar underdog, every horse on that list earned their spot in history.
Next Steps:
To get a feel for the speed required to win this race, watch the replay of Secretariat's 1973 Preakness. Pay attention to the move he makes on the first turn; it's a tactical masterpiece that explains why he still holds the stakes record today. Then, compare that to Swiss Skydiver’s 2020 win to see how a modern champion manages the same corners under pressure.