How Conquistador Cielo Launched One of Racing’s Most Incredible Streaks

In 1982, Woody Stephens was no stranger to big races and big victories. He had started training in the 1930s and, in 1952, won his first classic race when Blue Man took the Preakness.

It took Stephens 22 years before he won another classic. He saddled Cannonade to victory in the 1974 Kentucky Derby and, then, seven years passed. In those years, he won plenty of major stakes races — 16, to be exact — but to the average fan, it’s the classics that are remembered and Stephens was in a drought.

In 1981, he had a promising two-year-old colt named Conquistador Cielo. The bloodlines were there with Mr. Prospector the sire and Bold Commander the broodmare’s father.

Conquistador Cielo began his two-year-old campaign with a third-place finish on June 29. He then won two in a row, including the Saratoga Special on Aug. 3, before he completed his freshman season with a fourth-place finish on Aug. 12. In 44 days, the colt raced four times — something to remember for later.

Stephens’ colt opened his 3-year-old season by finishing fourth in an allowance race at old Hialeah Park and, 10 days later, won at the same track. The goal was the Kentucky Derby, but a leg injury put that in peril. After some contemplation, the decision was made to keep him out of the Run for the Roses. One week later, on May 8, he won an allowance race at Pimlico, but Stephens didn’t think the colt was ready for the Preakness Stakes.

The 3-year-olds were busy running the classics, with Gato del Sol taking the Derby and Aloma’s Ruler the Preakness, so Stephens was wondering what to do next with his colt.

He decided to enter Cielo in the Metropolitan Handicap, a race often referred to as the “Met Mile”. The Met Mile was run on Memorial Day, May 31, 1982, and was open to 3-year-olds and up. In just his eighth career start, Cielo would face older horses for the first time.

It was not a pretty day on Long Island, with gray skies, some rain and a heavy track, but Conquistador Cielo enjoyed it. He won by 10 lengths and ran the mile in a stunning 1:33.

Stephens, cocksure and, to some, a bit of a braggart, now knew that the colt was fit and ready and talked about running him back just five days later in the 1 ½-mile Belmont Stakes. Stephens asked a few people and most said it would be crazy to not only come back in five days, but to come back in a 12-furlong race. Some thought two races in six days was crazy enough, while others believed that Cielo wanted no part of 1 1/2 miles.

Stephens decided to enter the colt anyway, after securing the blessing of Conquistador Cielo’s owner Henryk de Kwiatkowski, who is credited by many for saving Calumet Farm in the 1990s.

“We’re going to run,” Stephens said.

Belmont Day was uglier than Memorial Day. Heavy rain and dark skies greeted the patrons, as a field of 11 were preparing to battle in a race referred to as “The Test of the Champion”.

The field included Kentucky Derby winner, Gato del Sol, and the Preakness winner, Aloma’s Ruler. For Cielo, regular rider Eddie Maple was in the hospital, so Stephens had to go to the bullpen. There, he found a “decent” rider — Hall of Famer Laffit Pincay, Jr. — and drew post 11 for the marathon run at Big Sandy.

The race was never in doubt.

Despite going very wide at the start, Cielo was able to grab the lead by the quarter pole. He cut fractions of :23 4/5, :47 1/5 and 1:12, while receiving token pressure from High Ascent. By the time they hit the one-mile mark, the race was over. Conquistador Cielo, who many thought couldn’t go the Belmont distance, kept pulling away to win by 14 lengths in 2:28 1/5. Pincay had an easy day in the saddle — he never used or even showed Cielo the whip.

For Stephens, it was validation on a couple of fronts. To begin with, he proved that horses can run back on short rest. Conquistador Cielo’s Met Mile and Belmont wins were both devastatingly good, but the second race might have been more dominant than the first — with a supposedly tired colt. Today, we see horses go weeks and months between starts and, while training techniques always change, we are often deprived of seeing the great ones run more often.

Imagine the scene and storyline back in 1982. The first would have been the intrigue of running a 3-year old against older horses in the legendary Met Mile. Then, the guts, courage or stupidity of trainer Stephens attempting to wheel the colt back just five days later in the Belmont.

In the end, Stephens had the last laugh and here we are, 36 years later, still talking about that incredible double by an incredible colt.

Conquistador Cielo would go on to win Horse of the Year honors and, after his Met/Belmont double, he would win the Dwyer at Belmont and Jim Dandy at Saratoga, ending his racing career with a third in the Travers. In 13 starts, he had 9 wins and 2 thirds. He was sold to stud duty for a then-record $36.4 million. A knee injury resulted in him being euthanized in 2002 at the age of 23.

At age 69, Stephens was just getting started. In 1983, he would win the Belmont with Caveat and would win it again in 1984, 1985 and 1986 with Swale, Crème Fraiche and Danzig Connection respectively. He also won the Kentucky Derby with Swale and would capture the Travers in 1988 with a pretty fair horse named Forty Niner.

The Woody Stephens Stakes, a 7-furlong affair contested on Belmont Stakes Day, is a fitting tribute to a man who dominated one of our nation’s great horse races. Most remember Stephens as the guy that won five consecutive Belmont Stakes, but fewer remember how that streak began back on Memorial Day 1982 with a plucky colt named Conquistador Cielo.