Each of the Triple Crown classics started as a race that was grounded in the history of its distinct location, a celebration of the sporting tradition of its region. Their union into one accomplishment came with its share of fits and starts, an evolution that was both influenced by and influential to decisions that made them the Triple Crown.

The Preakness Stakes started as a commemoration of a horse significant to Pimlico Race Course’s history and now has become an integral part of the sport’s calendar, finally settling into its spot on the third Saturday in May, securing its status as one of racing’s traditional prizes.

Origin Story

Gov. Oden Bowie had such a good time at an 1868 dinner party given by Milton Sanford that he decided to commemorate the occasion with the promise to build a racetrack for a stakes named in the evening’s honor. Two years later, a field of eight, including Sanford’s own Preakness, met the starter for the two-mile Dinner Party Stakes on Pimlico Race Course’s opening day. Preakness won by a length, and with that, a legend was born. In 1873, Pimlico added a stakes race in honor of Sanford’s horse, the winner of the track’s first signature race – the new Preakness Stakes a feature for the track’s opening day.

For its first 16 editions, the Preakness Stakes was a mile-and-a-half race for 3-year-olds, its date moving around on the calendar throughout those years but staying in May during the track’s spring meet. The 1889 running, the last one at Pimlico for two decades, was 1 ¼ miles, the two-horse field a sign of the times for the Baltimore racetrack. Financial issues plagued the Maryland Jockey Club, which operated Pimlico under a lease, owing to competition from regional racetracks. As of 1890, the United States counted 314 racetracks in operation and the competition for horses was strong. After the 1889 meet, the Maryland Jockey Club relinquished its lease on Pimlico.

Though Pimlico continued to host Standardbred racing intermittently, Thoroughbred racing would not return to the track for more than a decade and many of the track’s signature stakes went on a hiatus save for one: the Preakness.

Next Chapters

A March 1948 article from the Associated Press’s George Bowen shared a startling discovery: lost Preaknesses! During Pimlico’s hiatus, as the Maryland Jockey Club unearthed, a race called the Preakness was run first at Morris Park in 1890 (on the same card as the Belmont Stakes) and then at Gravesend from 1894 to 1908. Included in what was assumed to be these lost editions were two fillies Flocarline and Whimsical, the first two females to win the historic stakes. The schedule for this version of the Preakness kept it as a late spring/early summer feature, Though the how or why behind these New York editions are still unknown, the Maryland Jockey Club was able to produce enough evidence of the connection between those runnings and the stakes originated at Pimlico in 1873 to make those lost editions part of the race’s historic record.

William P. Riggs (Maryland Jockey Club photo)

Racing returned to Pimlico in 1904 when a new version of the Maryland Jockey Club, an effort spearheaded by William P. Riggs, emerged and leased the racetrack from the Maryland State Agriculture and Mechanical Association. Five years later, the race that would become the track’s signature stakes returned to its calendar. Scheduled for the last day of the spring meet, that 1909 edition was contested at a mile and featured a field of 10, including W.T. Ryan’s Effendi, who won by a length. In 1911, the Maryland Jockey Club changed the distance to 1 1/8 miles, the distance it stayed at until 1925, when they added an extra sixteenth of a mile to make the Preakness its current 1 3/16 miles. That was not the only change that would happen in the 1920s.

Since its inception in 1875, the Kentucky Derby had been a fixture on the opening day of Churchill Downs’s spring meet while the Preakness had moved around on the calendar during its tumultuous early decades. Because the two races were not linked together as anything of import, the dates were not as important to the sport as they would later become. Between 1875 and 1918, only three horses competed in both races – Vagabond (1875), Hindus (1900), and Norse King (1915) – owing to the difficulty of going between Louisville and Baltimore, which are just over 600 miles apart. In 1917, when the two races were scheduled on the same day, Saturday, May 12, the coincidence went unremarked by turf writers as Omar Khayyam was victorious under the Twin Spires while Kalitan took home the Woodlawn Vase, the first year that trophy was associated with the Preakness. When the two overlapped again in 1922, the stakes were much higher thanks to a horse named Sir Barton.  

Evolution of Time

Sir Barton broke his maiden in the 1919 Kentucky Derby, contested on May 10, and brought home the winner’s share of a purse of $25,000. Twelve hours later, he was on a train to Baltimore to start in the Preakness Stakes, which also featured a purse of $25,000 and was scheduled for May 14. The previous year the purse had been $15,000 and drew an oversubscribed Preakness, which the Maryland Jockey Club elected to run in two divisions. Because of that bump in purse money, Sir Barton was wheeled back for the Preakness, four days after his win in Louisville. Sir Barton won easily, and the idea of the Derby-Preakness double was born, which would figure into the challenges of 1922.

The last day of Pimlico’s spring meet and the first day of Churchill’s were the same day, May 13. When the two tracks announced their respective schedules, owner, trainers, and turf writers all tried to appeal to those in charge, Riggs of the Maryland Jockey Club and Col. Matt Winn of the Kentucky Jockey Club, which ran Churchill Downs. The two tracks raised their respective purses, trying to attract the year’s top 3-year-olds to their tracks, while also refusing to consider any sort of change to the date. On May 13, 1922, at 4:40 p.m., 12 horses went to the post for the Preakness Stakes, won by Pillory; 10 minutes later, 10 3-year-olds lined up at Churchill Downs, Morvich coming away with an easy victory. The following year, Winn announced that the Kentucky Derby would be run on the second Saturday of the meet, May 19, while the Preakness remained in its customary spot on the final day of Pimlico’s spring meet, May 12, a week earlier.

Citation winning the 1948 Preakness. (BloodHorse Library/Bert Morgan)

The two races remained in this order, five to eight days separating them, until 1932, when the Derby moved to the first Saturday in May. (Note: War Admiral in 1937 won the Kentucky Derby on May 8, the second Saturday of the month). From 1932 to 1955, the gap between the two races varied from one week to three weeks, which meant that the gap between the Preakness and Belmont was anywhere from three to four weeks with the exception of 1945. The current five-week schedule has been in place since 1956 and only the most recent five Triple Crown winners – Secretariat, Seattle Slew, Affirmed, American Pharoah, and Justify – have earned their titles with this familiar calendar.

In its 150 runnings, of course, the Preakness has been at the mercy of forces outside of racing twice, first in 1945 when the War Department curtailed racing for the first half of the year as World War II entered its final phases, and then in 2020, when the COVID-19 pandemic required a reconfiguring of the racing calendar for that year. When the war in Europe ended on May 7, 1945, racing resumed right away and the Triple Crown was scheduled for June, with the Derby on June 9, the Preakness on June 16, and the Belmont Stakes on June 23. In 2020, the powers that be behind the Derby and the Preakness elected to move their races to later in the year, September and October respectively, to give each time to prepare while the New York Racing Association elected to delay the Belmont by two weeks.

Over its 150 years, establishing the Preakness Stakes as a mid-May staple on the racing calendar reflects how the traditions of Triple Crown came to be. While the early years saw many shifts in dates, its place in our sporting consciousness underscores the enduring legacy of the Preakness and its status as one of racing’s essential prizes.