Winning But Losing: How a Coin Toss Cost a Yale Grad’s Family the Triple Crown

By Philip R. Devlin.

The second leg of the Triple Crown for horse racing will be contested this coming Saturday at “Old Hilltop” — the Pimlico Racecourse in Baltimore, MD. Former New Haven resident and Yale grad Ogden Mills Phipps hopes that his Kentucky Derby winner, Orb, can capture the second and shortest leg of the Triple Crown.

Despite being in the breeding business since 1926, the family has never before won the Triple Crown, but they’ve come tantalizingly close. A coin toss in 1969 won by Phipps’ father could have brought Triple Crown glory to the family in 1973 but didn’t.

Based on an agreement between Wheatley Farm owned by the Phipps family and Meadow Stable owned by the Chenery family, the winner of the coin toss had the first pick of two foals sired by the influential sire Bold Ruler. Mr. Phipps won the toss and chose a filly sired by Bold Ruler out of a productive mare named Hasty Matelda.

Penny Chenery then was left with a yet-unborn foal by Bold Ruler out of the mare Something Royal. That foal was born on March 30, 1970, and was a bright red chestnut colt with three white socks and a narrow white blaze on his head. As a 2-year-old he was given the name “Secretariat.”

As the Triple Crown can only be contested by 3-year-old horses, Secretariat entered the Triple Crown picture on the first Saturday in May of 1973 — the traditional date on which the Kentucky Derby is run.

He had come into the Derby with a stellar record of five stakes wins during his 2-year-old season. Even though Secretariat had lost his Derby prep — the Wood Memorial at Aqueduct — he had an excuse: a large abcess in his mouth.

Sent off as the 3-2 favorite in the Derby, Secretariat beat Sham by 2.5 lengths in 1:59.2 — a track and stakes record that still stands. Each of his successive ¼ mile split times were faster than the ones before them — a fact that is simply amazing! His performance seemed other-worldly.

Secretariat entered the Preakness two weeks later as the overwhelming favorite. After breaking last, “Big Red” passed the field on the first turn and never looked back, again beating Sham by 2.5 lengths and again in track record and stakes record time. It was a breath-taking performance. Three weeks later, however, the big chestnut would out do himself in the Belmont Stakes.

The longest of the three races in the Triple Crown at 1.5 miles, the Belmont is the supreme test of stamina and speed. Just prior to the contest, Secretariat became the first horse ever to appear on the cover of three national magazines: Time, Newsweek, and Sports Illustrated. He was a celebrity. His performance was one for the ages.

After running Sham into the ground after 3/4ths of a mile, he then continued to widen on the field, winning by over 31 lengths in a record-shattering time of 2:24.

CBS race announcer Chick Anderson’s famous description was this: “Secretariat is widening now! He is moving like a tremendous machine!” No other horse in history has ever broken 2:25 for 1.5 miles. Jockey Ron Turcotte never drew his whip. He sat like a statue on the big chestnut. One can only wonder what was going through the mind of Ogden Phipps, who could have chosen Secretariat but didn’t.

Secretariat’s record-setting performances in the Triple Crown races remain intact. He still holds the track and stakes records for Churchill Downs, Pimlico, and Belmont Park for the Triple Crown race distances after 40 years! It is nearly impossible to find a 40-year-old record in any sport that still stands, yet Secretariat still holds those three.

Secretariat was retired to stud after his 3-year-old season, having won 16 of his 21 races. He stood at stud for over 15 years before contracting laminitis. He had to be euthanized on Oct. 4, 1989.

An autopsy revealed a stunning fact about Secretariat: His heart, weighing about 22 pounds, was nearly four times the size of the heart of a normal horse! The University of Kentucky pathologist who performed the autopsy on Secretariat said this: "We just stood there in stunned silence. We couldn’t believe it. The heart was perfect. There were no problems with it. It was just this huge engine.”

A list of the top 100 greatest individual sports performances ever achieved shows one animal on that list: Secretariat’s Belmont performance at No. 2. Only Wilt Chamberlain’s 100 point game in 1962 was ranked higher.

So as the dark bay colt named Orb attempts to bring home Triple Crown glory this coming Saturday for the Phipps family by winning the Preakness, keep in mind that 40 years ago the family must have watched Secretariat’s stunning Triple Crown performance of 1973 with mixed emotions.

The wrong choice in a coin toss prevented them from owning the great Secretariat and Triple Crown glory. The Phipps family can take heart, however, in knowing that Secretariat is the third grandsire of Orb, so you know he packs the pedigree power to win the Triple Crown!

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