Who is the Greatest Preakness Winner of all Time?

by Katherine O. Rizzo (first published in the May 2025 Equiery)

The year was 1873, and Thoroughbred racing was booming across the mid-Atlantic. Just three years after the official grand opening of Pimlico Racecourse in Baltimore, Governor Oden Bowie requested the Maryland Jockey Club to hold a big stakes race at the new track which he had built on land leased by MJC from the Maryland Agricultural Society. The idea was to bring the best of the best horses to Maryland to run in a race at a track he felt was grander than others in the U.S. That “big stakes” race became the Preakness Stakes, which was run for the very first time on May 23, 1873.

The Preakness Stakes was named after a large bay colt who won the very first Dinner Party Stakes on opening day at Pimlico in 1870. The colt was bred by Robert A. Alexander in New Jersey and owned by Milton H. Sanford and later, the Duke of Hamilton. After winning 11 stakes races in five years, Preakness was sold to the Duke and shipped to England where he was later shot by the Duke in a drunken rage.

Survivor galloped to victory by 10 lengths to become the Preakness’ first winner. Survivor’s record stood for another 131 years until Smarty Jones won by 11.5 lengths in 2004. Smarty Jones still holds the record for the largest winning margin in the Preakness Stakes.

It was not until 1935 that the phrase “Triple Crown” was penned by popular sportswriter Charles Hatton who used the term when reporting on Maryland-breds Gallant Fox and his son Omaha’s wins of the Kentucky Derby, Preakness Stakes and Belmont Stakes in 1930 and 1935, respectively. Triple Crown Productions was created in 1985 by the owners of Churchill Downs (KY), Pimlico (MD) and Belmont Park (NY) to officially create the Triple Crown as we know it today.

Many racing fans may feel that the greatest racehorses of all time are those who are Triple Crown winners, however here in Maryland, other Preakness winners hold that honor. The Equiery conducted a poll asking our readers “Who is the greatest Preakness winner of all time?” and while the majority stated that honor has to go to Secretariat, stories and memories about other great Preakness winners were also shared.

Secretariat (1973)
In 1973, a big red colt bred and owned owned by Meadow Stable in Virginia romped to victory in the Kentucky Derby. As Secretariat and his connections, jockey Ron Turcotte, and trainer Lucien Laurin, arrived at Pimlico, racing fans were just itching for another Triple Crown winner as no one had taken that honor since Citation in 1948. On May 19, 1973, Secretariat broke from the starting gate last, which was is how he had started every race leading up to the Preakness. This time however, he made a move to the lead in the first turn instead of later in the race. His closest challenger that day was a horse named Sham, who finished second by 2 ½ lengths. Sham had also finished second to Secretariat in the Kentucky Derby and then second again in the Belmont Stakes, which Secretariat won by 31 lengths. Secretariat went on to win five Eclipse Awards, including Horse of the Year for his two- and three-year-old seasons.

Considered by many around the world as the greatest racehorse of all time, Secretariat was the clear favorite of Maryland racing fans as well.

“The greatest [Preakness] winner (and of all time!) was Secretariat. No question. No argument. Then going on to win the Belmont with a 31-length lead.” – Stacy Frank (Tuckahoe Equestrian Center)

“Has to be Secretariat. Not only because he won the Triple Crown, but the way he ran in the Preakness, winning very convincingly.” – Frank Douglas (Jockey’s Agent, Sunrise Tour Guide) Editor’s note – Frank Douglas rode Silver’s Prospect in the 1998 Preakness Stakes

“Secretariat of course. No explanation needed!” – Donna Sullivan (Sunrise Tour Guide)

“Secretariat! Because he was the G.O.A.T! Period!” – Jane Seigler (Dressage at Sundown, MHC co-chair Government Relations Committee)

“Big Red holds the Preakness Stakes record and still is considered the greatest racehorse of all time. He’s almost a Marylander, hailing from Virginia, but that’s not his fault. And what other Preakness winner has had a larger-than-life bronze sculpture made to honor him or her? And a woman owner? What other horse can compete with all that?” – Varlerie Ormond (CEO Veteran Writing Services, LLC)

“It was 1973, I was just a kid standing in the walkway [of Pimlico] watching Secretariat being led into the paddock. He oozed racehorse. Something about him simply was a racehorse through and through. He carried the spirit of the sport in every step.” – Jenile Tapscott (racing representative on the Maryland Horse Industry Board, Sunrise Tour Guide)

“My obvious answer [to which horse is the greatest Preakness winner] is Secretariat. Big Red. The ground that “Miss Penny” broke for women in racing….” – Sally Eck (Sunrise Tour Guide)

“Secretariat. I love Big Red. I love the history, his stride, his love of the camera, his trainer and his groom. A superstar among Thoroughbreds and among all equines.” – Wendy Albert (Sunrise Tour Guide)

Funny Cide (2003)
The New York-bred chestnut Funny Cide was a fan favorite even in his retirement at the Kentucky Horse Park where he lived until he was 23. Funny Cide, owned by Sackatoga Stable and trained by Barclay Tagg, entered the Preakness Stakes as the Kentucky Derby winner and the newest Triple Crown hopeful. Tagg shipped the gelding to Pimlico at the last moment and stabled him in Mary Eppler’s barn to keep him calm and away from the press. Race day was cold and rainy but that did not seem to bother Funny Cide at all. The gelding broke quickly, ran to the front, and did not let anyone catch him, winning by 9 ¾ lengths. At the time, that was the second largest margin in Preakness history.

“For me, it is Funny Cide! The gutsy gelding was my 12-1 pick in the 2003 Derby and won the Preakness by 9 ¾ lengths. Loved how his ‘average guy’ owners traveled in a school bus to watch him race. Thrilled when I got to see him at the Kentucky Horse Park when he was 20. The ‘People’s Horse’ running in the ‘People’s Race’!” – April Inloes Smith (MHC member and Sunrise Tour Guide)

“Funny Cide – the first Preakness to which I took my daughter. She had been to the races before but nothing like that!” – Denise Carnes (Sunrise Tour Guide)

I’ll Have Another (2012)
In 2012, Kentucky-bred I’ll Have Another came to Pimlico having just won the Kentucky Derby. Trained by Doug O’Neill and owned by his breeder J. Paul Reddam, I’ll Have Another was not the favorite on Preakness day. Bodemeister was the Preakness favorite and set the pace early in the race. In the final turn, I’ll Have Another moved into second place and caught Bodemeister at the wire to win by a neck. Entered in the Belmont Stakes, O’Neill pulled the horse due to a tendon injury which ended I’ll Have Another’s racing career.

“California’s Doug O’Neill and his team connected with our Sunrise Tour guests very closely. We all got to know them and I’ll Have Another up close. I worked that year also in the hospitality tent [at Pimlico] so I saw them all week. To see their overwhelming excitement for the win and to be included in their celebration was unforgettable for me.” – Fran Burns (President, Maryland State Fair & Agricultural Society, Lead Sunrise Tour Guide)

“I’ll Have Another – The entire team that came with him really embraced all of Baltimore and were fantastic to have at Pimlico.” – Posey Obrecht (My Lady’s Manor Steeplechase Director, Sunrise Tour Guide)

Additional Fan Favorites
“Afleet Alex (2005). Heart of a Champion.” – Justine Howell (Sunrise Tour Guide).

“Ah, so many good ones! But I have to go with my favorite girl who won in 2009. Rachel Alexandra. The first filly to win the race in 85 years – and with the looks, personality and charm of a true champion.” – Brooke Fox (Charis Realty Group)

“Deputed Testamony (1983) because of his local connections.” – Erika Taylor (UMD Extension, Sunrise Tour Guide). Editor’s note – Deputed Testamony, bred by the Boniface family at Bonita Farm in Darlington, is the last Maryland-bred to have won the Preakness Stakes.

“California Chrome (2014) because Michelle (my daughter) and I were right up on the rail. A group of college kids were next to us. They knew nothing about horse racing so it was fun to share our experience.” – Lynn Russell (Sunrise Tour Guide)

“Damascus (1967) – He is the grandfather of my horse of a lifetime, Wrotten, and had strong ties to Maryland through his trainer, Frank Whitely of Centerville, Maryland.” – Martha Delaney (Sunrise Tour Guide)

“Everyone was talking about the Kentucky Derby winner American Pharoah (2015) leading up to the Preakness and how he could be the one to break the Triple Crown drought, but I’ll admit, I had my doubts. Then I stood on a chair under an awning at Pimlico while the rain came down in buckets and watched that bright bay colt streak out of the gate, take the lead and win wire to wire. Just an incredible, uncontested win by an incredibly athletic horse in some of the worst racing conditions ever.” – Katherine O. Rizzo (Equiery Editor-in-Chief, Waredaca Pony Club Center Administrator)

Almost a winner…
“Magic Weisner [who finished second in 2002] – I worked for Dr. Wisner for whom he is named. This horse had a joint infection when he was little. Dr. Wisner saved him. However, he gave all the credit to the horse’s breeder, Nancy Alberts, because Dr. Wisner knew she was a fabulous horsewoman and she would be able to care for the horse properly through his recovery. It was Nancy who spelled his name wrong on the JC papers! Extra fun aside: one of the women I worked with took $100 and made every bet, every which way she could on Magic Weisner in the Preakness and won $18,000! She bought a new pickup truck with the winnings!” – Katherine Powder (Sunrise Tour Guide) Editor’s note – The Maryland-bred Magic Weisner was sired by Ameri Valay and out of Jazema, by Bold Forbes.