From a Maryland gentleman's vision in 1873 — two years before the Kentucky Derby even existed — to the greatest test of America's three-year-old thoroughbreds.
Many people assume the Preakness was built around the Kentucky Derby — a second race added to follow the famous Run for the Roses. In fact, the opposite is closer to the truth. The Preakness Stakes was first run on May 27, 1873 — two full years before the Kentucky Derby was established in 1875. Pimlico Race Course opened in 1870, making it one of the oldest continuously operating racetracks in North America.
The race is named after Preakness — a colt owned by Milton H. Sanford who won the Dinner Party Stakes at Pimlico in 1870, the very first important race held at the track. The name "Preakness" itself derives from a township in New Jersey where Sanford had his breeding operation. The first Preakness Stakes was won by Survivor, who won by ten lengths in a time of 2:43 at the original distance of 1&frac1;2 miles.
Unlike the Derby, which ran continuously from 1875, the Preakness had an interrupted early history — the race was not held at all from 1890 to 1893 due to financial difficulties and a brief relocation of stakes racing from Baltimore. It was revived in 1894 and has run without interruption ever since.
The early 20th century brought standardization to the Preakness — and growing recognition of its place alongside the Derby as a premier test for three-year-olds. The distance was adjusted several times before settling at the current 1&frac3;16 miles in the early 1920s, making it the shortest of the three Triple Crown races.
The concept of the Triple Crown as a named series did not exist in the race's early decades — horses simply ran the three important spring races, and those that won all three were noted for exceptional achievement. Sir Barton became the first horse recognized retroactively as a Triple Crown winner in 1919 — but the term "Triple Crown" wasn't widely used until the 1930s, and official recognition came even later.
The Preakness gained enormous prestige in 1920 when Man o' War — arguably the most dominant racehorse of the 20th century — ran at Pimlico. Man o' War did not race in the Kentucky Derby (his connections opted out) but crushed the Preakness field by 1&frac1;2 lengths despite a difficult start. Man o' War's performances at Pimlico and elsewhere in 1920 cemented the track's status in American racing.
The 1930s and 1940s produced the most concentrated run of Triple Crown champions in history — six in eighteen years. Each Preakness victory during this era was part of a championship narrative that captured the public imagination.
Gallant Fox (1930) became the second official Triple Crown winner, sweeping all three races with jockey Earl Sande aboard. His son Omaha (1935) repeated the feat five years later — the only father-son pair ever to win the Triple Crown. War Admiral (1937) added a third Triple Crown in a seven-year span, completing a run that would not be repeated in such rapid succession for decades.
Whirlaway (1941) and Count Fleet (1943) added two more Triple Crowns during the World War II era, with Count Fleet winning the Preakness by eight lengths as part of his dominant sweep. Assault (1946) and Citation (1948) capped the golden era. Citation, in particular, was considered the greatest American thoroughbred since Man o' War — his Preakness victory was part of a season in which he won 19 of 20 starts.
Since 1909, the winning owner of the Preakness Stakes has received a replica of the Old Woodlawn Vane — a 19th-century weather vane from the old Woodlawn Course in Louisville, topped with a horse-and-rider figure. The original vane is kept at the National Sporting Library in Virginia. The trophy is one of the most distinctive in American sport — a piece of history, not a generic cup or plate.
After Citation in 1948, a quarter-century passed without a Triple Crown winner — the first great drought in the series' history. During those 25 years, several horses won the Derby and Preakness only to fall short at Belmont. The Preakness became, for many of these near-miss years, a tantalizing second step that made the Belmont failure feel even more devastating.
The drought ended dramatically in 1973, when Secretariat arrived at Pimlico as one of the most heavily favored horses in modern memory. His Kentucky Derby performance had been historic — a record 1:59.4 with each quarter-mile faster than the last. The Preakness proved equally breathtaking: Secretariat won by 2&frac1;2 lengths and set a track record of 1:53.0 that stood for decades before a controversy arose over the official timing equipment used that day. Many historians believe the true time was even faster.
Secretariat went on to win the Belmont by 31 lengths — a performance so extraordinary that his three Triple Crown races are studied in thoroughbred racing courses to this day. His Preakness win remains among the most celebrated in the race's history.
The sport produced an extraordinary back-to-back run of Triple Crown champions in 1977 and 1978 — a feat that has never been repeated. Seattle Slew became the first undefeated horse to win the Triple Crown, arriving at Pimlico in 1977 without a single career loss. He won the Preakness by 1&frac1;2 lengths and went on to complete the sweep at Belmont.
The following year, Affirmed and Alydar continued one of the great rivalries in American racing history. The two horses finished first and second in all three Triple Crown races of 1978 — separated by fractions at each finish. Affirmed won the Preakness by a neck after a furious battle down the stretch. In a sport where individual greatness is celebrated, the mutual excellence of Affirmed and Alydar that spring was something rare: two horses making each other better, race by race.
The second Triple Crown drought — spanning 37 years from Affirmed to American Pharoah — transformed the Preakness into a recurring theater of hope and heartbreak. Fourteen times between 1979 and 2014, a horse won both the Derby and Preakness and arrived at Belmont with the Triple Crown in reach. Fourteen times, the dream was extinguished.
Among the most memorable near-misses: Spectacular Bid (1979) stumbled in the Belmont after stepping on a pin in his stall the night before the race. Charismatic (1999) suffered a career-ending injury in the stretch of the Belmont while leading. Real Quiet (1998) lost the Belmont by a nose in a photo finish. Smarty Jones (2004) led comfortably in the Belmont stretch before being run down by Birdstone — one of the sport's cruelest upsets.
The Preakness during these years was often the high-water mark — the moment where Triple Crown dreams were alive before the Belmont trip arrived to shatter them.
American Pharoah (2015) arrived at Pimlico having won the Kentucky Derby by a length. His Preakness was dominant — he led wire to wire and won by seven lengths, the largest Preakness margin in years. The nation watched with bated breath as he headed to Belmont. Three weeks later, American Pharoah ended the 37-year drought with a 5&frac1;2-length Belmont victory, the crowd roaring before he even crossed the wire.
Justify (2018) — trained by Bob Baffert, ridden by Mike Smith — provided the most recent Triple Crown sweep. His Preakness came in a driving rainstorm on a sloppy track, the kind of conditions that can shuffle racing results unpredictably. Justify handled the mud with authority, winning by a half-length. Two weeks later at Belmont, he added the third leg and cemented his place among the greats.
The years since Justify have seen the Preakness produce several memorable upsets and storylines. In 2020, the race was held in October without fans due to the COVID-19 pandemic — a surreal Preakness that saw Swiss Skydiver become one of the very few fillies in history to win the Preakness Stakes, defeating the heavily favored Authentic (who had won the Derby earlier that year) by a neck.
Rombauer (2021) delivered one of the great Preakness upsets in recent memory — a 11-1 longshot who had finished third at the Derby, came to Pimlico fresh, and destroyed the field by 3&frac1;2 lengths while the Derby's top two horses, Medina Spirit and Midnight Bourbon, faded. It was a textbook example of a fresh horse exploiting tired competitors who had just run the demanding Kentucky Derby.
Early Voting (2022) provided another fresh-horse victory — trained by Chad Brown, he skipped the Derby entirely and demolished the Preakness field by 4&frac1;4 lengths. The 2023 Preakness was won by National Treasure, trained by Bob Baffert — who won despite controversy surrounding his training relationship with Pimlico. Seize the Grey (2024) and Journalism (2025) continued the tradition of close, competitive Preakness finishes.
| Year | Winner | Jockey | Trainer | Time | Odds |
|---|---|---|---|---|---|
| 2025 | Journalism | Umberto Rispoli | Michael McCarthy | 1:54.86 | 5-2 |
| 2024 | Seize the Grey | Jaime Torres | D. Wayne Lukas | 1:55.80 | 9-2 |
| 2023 | National Treasure | John Velazquez | Bob Baffert | 1:53.83 | 5-2 |
| 2022 | Early Voting | Jose Ortiz | Chad Brown | 1:53.39 | 5-2 |
| 2021 | Rombauer | Flavien Prat | Michael McCarthy | 1:53.62 | 11-1 |
| 2020 | Swiss Skydiver | Robby Albarado | Kenny McPeek | 1:53.28 | 5-1 |
| 2019 | War of Will | Tyler Gaffalione | Mark Casse | 1:54.05 | 9-2 |
| 2018 | Justify | Mike Smith | Bob Baffert | 1:55.93 | 3-5 |
| 2017 | Cloud Computing | Javier Castellano | Chad Brown | 1:55.98 | 13-1 |
| 2016 | Exaggerator | Kent Desormeaux | Keith Desormeaux | 1:58.31 | 5-1 |
| 2015 | American Pharoah | Victor Espinoza | Bob Baffert | 1:58.46 | 2-5 |
| 2014 | California Chrome | Victor Espinoza | Art Sherman | 1:55.50 | 1-5 |
| 2013 | Oxbow | Gary Stevens | Dale Romans | 1:57.54 | 15-1 |
| 2012 | I'll Have Another | Mario Gutierrez | Doug O'Neill | 1:55.98 | 9-2 |
| 2011 | Shackleford | Jesus Lopez Castanon | Dale Romans | 1:56.67 | 12-1 |
| 2010 | Lookin At Lucky | Martin Garcia | Bob Baffert | 1:56.52 | 3-2 |
Man o' War won 20 of his 21 career starts — his only loss to a horse appropriately named Upset. At Pimlico in 1920, Man o' War won the Preakness by 1&frac1;2 lengths despite breaking slowly from a bad position. His combination of raw speed, physical power, and competitive drive was unprecedented. He remains one of the most celebrated racehorses in American history, and his Preakness win helped cement Pimlico's reputation as a stage for greatness.
Secretariat's Preakness was as extraordinary as his Derby run — he won by 2&frac1;2 lengths and many observers believe the official time of 1:55.0 was actually mis-measured and that the true time was closer to 1:53.0, which would make it the fastest Preakness ever run. Whether or not the timing equipment was accurate, what was undeniable was the performance: Secretariat was on another level from every other horse in the race. His three Triple Crown performances collectively represent the greatest sustained month of racing any thoroughbred has ever delivered.
The 1978 Preakness was the middle act of the greatest head-to-head rivalry in Triple Crown history. Affirmed and Alydar had been meeting all spring — Affirmed always winning, Alydar always close. The Preakness was decided by a neck after a furious stretch battle, with Alydar coming back in the final yards before Affirmed held on. The photograph of the two horses at the wire — neither willing to yield — captures everything that made their rivalry so compelling.
In a COVID-displaced Preakness run in October without fans, Swiss Skydiver became the sixth filly in Preakness history to win the race, defeating the heavily favored Authentic (the Kentucky Derby winner) in a driving finish. Her trainer, Kenny McPeek, had targeted the Preakness specifically and prepared her to handle the unusually late calendar and the pressure of racing against the best males of her generation. Her win remains one of the most dramatic Preakness outcomes of the modern era.
Rombauer's 2021 Preakness is the textbook case for why trainers consider skipping the Derby. He had finished third at Churchill Downs, then came to Pimlico with two extra weeks of rest while the Derby's top two horses — Medina Spirit and Midnight Bourbon — showed the fatigue of their earlier effort. Rombauer crushed the field by 3&frac1;2 lengths. His win is cited every spring when trainers decide whether to target the Derby or the Preakness with a fresh horse.