Woody Stephens: Hall of Famer Won Remarkable Five Belmont Stakes in a Row

Woody Stephens and Cannonade at the 1974 Kentucky Derby.
Woody Stephens and Cannonade at the 1974 Kentucky Derby. (Blood-Horse photo)

A list of Woodford Cefis Stephens’ accomplishments could pretty much fill a chapter of an encyclopedia.

In a career that started in the 1930s and lasted into the 1990s, the Hall of Fame trainer known as “Woody” was revered as one the sport’s most respected and beloved figures. He won eight Triple Crown races, saddled nine champions and received enough trophies from his stakes wins to stock a three-story museum.

Woodford Cefis Stephens

Birthplace: Stanton, Ky.

Birthdate: Sept. 1, 1913

Died: Aug. 22, 1998

Champions trained: Conquistador

Cielo, De La Rose, Devil's Bag,

Forty Niner, Heavenly Cause,

Sensational, Smart Angle, Swale.

Notable: Inducted into Hall of

Fame in 1976; won Eclipse Award

as outstanding trainer in 1983.

But late in his life, whenever he would engage in a conversation about his profession, he would grin like the Cheshire Cat and then mention the one accomplishment that he prized above all the others.

“You know,” the Kentucky native would say, “I won five Belmonts.”

Yes, Woody Stephens won five Belmont Stakes. In a row, no less. A feat that can be considered racing’s answer to Joe DiMaggio’s 56-game hitting streak. Some might come close, but break it? We may never see that.

“I am absolutely sure that no one will ever break Woody’s record,” trainer Bill Badgett, an assistant with Stephens during his incredible run, said in an ESPN.com story. “I don’t know how long it will be before someone runs a horse in five straight Belmonts, much less wins five straight.”

Stephens entered the Hall of Fame six years before he won his first Belmont Stakes in 1982. He had won the 100th Kentucky Derby in 1974 with Cannonade and trained champions like Bald Eagle and Never Bend at the time of his induction in 1976. Though 63 years old at the time, Stephens’ best years actually were still ahead of him when he received the sport’s greatest honor.

Aging like a fine wine, Stephens enjoyed his greatest measure of glory in the 1980s. Backed by a collection of deep-pocketed owners, Stephens’ barn was filled with some of the best-bred and fastest horses in America.

One of them was Conquistador Cielo, who in 1982 became Stephens’ first Belmont Stakes winner. Unable to compete in the first two legs of that year’s Triple Crown due to minor injuries, Conquistador Cielo prepped for the Belmont in the Grade 1 Metropolitan Handicap at a mile. Facing older horses, he won by 7 ¼ lengths in the track record time of 1:33. Five days later, he returned to take the 1 ½-mile final leg of the Triple Crown by an astonishing 14 lengths.

“Go figure,” former jockey Eddie Maple, one of Stephens’ regular riders, said to ESPN.com. “Woody ran a horse on five days rest and won the Belmont. Now you see horses running twice at three before the Kentucky Derby.”

Woody Stephens in 1988.
Woody Stephens in 1988. (Anne Eberhardt/Blood-Horse photo)

That victory stamped Conquistador Cielo as a superstar – a reputation that was tarnished by a loss later in the Travers Stakes – and paved the way for the son of Mr. Prospector to be named 1982 Horse of the Year and syndicated for $36.4 million as a stud prospect.

A year later, Stephens might have won his second Derby but Caveat had traffic issues and finished third. After skipping the Preakness, Caveat prepped in an allowance race at Belmont 12 days before the “Test of the Champion” and then took the Belmont by more than three lengths.

Stephens won his second Derby in 1984 with Claiborne Farm’s Swale, and after a disappointing seventh-place finish in the Preakness, Swale rebounded back home in New York and gave Stephens his third straight Belmont win with a four-length triumph.

Stephens’ dominance in the Belmont was vividly reflected in the 1985 Belmont when he sent out Crème Fraiche and Stephan’s Odyssey to finish 1-2 in the 117th edition of the classic.

Interestingly, of Stephens’ first four Belmont winners only Swale was favored.

His fifth was the most improbable of the bunch.

Danzig Connection was coming off a win in the Peter Pan Stakes but was sent off as the 8-1 co-fifth choice in a field of 10. On a sloppy track, he ran the race of his life and extended Stephens’ streak to mind-boggling proportions with a 1 ¼-length victory.

The glorious run ended when Gone West finished fifth in the 1987 Belmont and sadly his career began to ebb soon afterward as emphysema and heart disease took a toll on him.

Woody Stephens, right, with his 1974 Kentucky Derby winner Cannonade.
Woody Stephens, right, with his 1974 Kentucky Derby winner Cannonade. (Blood-Horse Library)

His stable amounted to just a handful of horses in the 1990s when his physical ailments forced him to carry oxygen with him so his frail body could breathe. He passed away in 1998 at the age of 84.

He left behind a legacy that extended far beyond that one sentence about his prowess in the Belmont Stakes.

“Woody breathed, drank, and ate horse racing, but he also loved to talk and entertain you,” trainer David Donk, a former Stephens assistant, said to ESPN.com. “To this day, I haven’t met anyone else like him. He was the best.”

Yet, as Stephens himself would no doubt tell you, while he cherished his plaque in the National Museum of Racing and Hall of Fame in Saratoga Springs, N.Y., there was a part of Belmont Park that he treasured just as much. It can be found on a wall in the clubhouse entrance to the track. Called “Woody’s Corner” it pays tribute to the great trainer by showcasing some of his most famous trophies and a large painting of Stephens aboard his pony, Rex, with his Belmont winners in the background.

It’s an impressive statement about the man and what he accomplished in racing.

After all, Woody Stephens did win five Belmonts, you know.

Note: This story originally was published in June 2016 and has been updated.

Fun Facts

  • The 5-foot-8 Stephens started in racing as a jockey but switched to training when he became too tall to maintain weight.
  • Stephens’ nine champions were Bald Eagle, Conquistador Cielo, De La Rose, Devil’s Bag, Heavenly Cause, Never Bend, Sensational, Smart Angle, and Swale.
  • One of the undercard races on Belmont Stakes day is the Woody Stephens Stakes at seven furlongs for 3-year-olds.
  • His last Belmont Stakes starter was Cefis, who was named after the trainer.
  • Stephens’ autobiography was entitled “Guess I’m Lucky.”
  • His first winner as a trainer was Bronze Bugle in 1940 at Keeneland.

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