Outdoors

Miami sailor brings home mystery trophy with Optimist win

Ivan Shestopalov, 15, holds the trophy, originally presented by the Miami Herald in 1962, that he received for winning the International Optimist sailing championship in 2014, on Thursday, Jan. 15, 2015, at the Coral Reef Yacht Club in Coconut Grove.
Ivan Shestopalov, 15, holds the trophy, originally presented by the Miami Herald in 1962, that he received for winning the International Optimist sailing championship in 2014, on Thursday, Jan. 15, 2015, at the Coral Reef Yacht Club in Coconut Grove. FOR THE MIAMI HERALD

The stately silver cup is engraved with “Miami Herald USA-Denmark Pram Challenge Perpetual Trophy.” It has made multiple trips around the world since it was created to honor young racers of the Optimist dinghy — the sailboat also known as the Pram — 50 years ago. The trophy’s last visit to the United States was in Miami in 1979 when a 14-year-old local named Shawn Lobree anchored the team that brought it back from Thailand.

Now, for the first time in 37 years, it’s back — decorating the living room table of the Shestopalov family in Miami after son Ivan, 15, and his four teammates won it for the best final points aggregate in last October’s Optimist World Championship in Argentina.

“It looks great,” said Ivan, a 10th-grader at Miami’s MAST Academy. “It would be interesting to find out the history.”

Somehow, the exact origins of the trophy remain a mystery.

The Optimist dinghy has been around since 1947 and is still the world’s most popular racing sailboat for youths up to age 15. Formerly called a “pram,” the single-handed boat is sailed in more than 120 countries and yields the largest fleet at the annual Orange Bowl International Youth Regatta on Biscayne Bay in late December.

According to Optimist-class historian Robert Wilkes of Ireland, the first International Optimist Regatta was held in England in 1962, but the first time the United States attended was in 1964, when the event was hosted by Denmark. Wilkes said the Miami Herald trophy was created in 1966 when the United States hosted the international regatta for the first time. Sweden won the trophy, which was awarded on the results of a single individual race among a handful of countries, including the United States and Denmark.

Interestingly, the award is engraved with winners from before the Herald started it. Wilkes said he thinks they were added “retrospectively.”

Wilkes said sometime between 1970 and 1981, the Herald trophy changed from a competition among the few teams originally involved to become open to all the countries represented at the world championships. In 1983, he said, the International Optimist Dinghy Association introduced genuine team racing where four-boat teams from participating countries sailed against each other in a knockout format. The IODA Challenge Cup went to the winners of that competition, and the Miami Herald trophy became the prize for the best aggregate team score, and was also known as the “Nations Cup.”

However, no one seems to remember who at the Herald created the trophy, and no information can be found about it in the newspaper’s archives.

Lobree, now a 49-year-old U.S. Navy captain who commands an ROTC unit at the University of Oklahoma in Norman, vaguely remembers that an “official from the paper came and congratulated” him and his teammates at a ceremony in 1979 at one of the yacht clubs in Coconut Grove, but he can’t remember exactly where. He said his father gave him a box full of records about his youth sailing career but they were lost during Hurricane Katrina in 2005.

“I recall my dad explained to me the Herald donated the money for the trophy,” Lobree said. “It’s really neat that from the early ’60s that it’s still in service and recognizing excellence in team racing.”

Lobree was thrilled to learn the trophy is now back in Miami after such a long absence.

“I want to pass along my congratulations,” he said.

The year Lobree and his teammates won might have been the last time anyone from the Herald handed out the big silver cup. From then on, it might have been passed along from the reigning champions to whoever hosted the awards ceremonies at the worlds each year to be presented to the new champs. When Ivan and his teammates won last fall, the trophy was brought to Argentina by representatives from Singapore.

The cup landed in Miami during the Orange Bowl Regatta in late December at the request of Ivan’s mother, Julia Shestopalov, who wanted the large contingent of U.S. Opti sailors to be able to see it. It was kept at Coral Reef Yacht Club for the duration of the regatta and then Julia took it home.

“I didn’t want the trophy to disappear or be misplaced,” she said.

The Shestopalovs aren’t sure how much longer they will have it here because it might rotate to the hometowns of the other U.S. team members.

Meanwhile, Dr. William Smoak — a Miami physician and former president of the U.S. Optimist Dinghy Association — has combed through reams of records without success.

Said Smoak: “I don’t think we’re ever going to find out where that trophy originated.”

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