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The 112-mile battle with Big Blue

A group of men deal with sharks and seasickness in the rough waters between Key West and Cuba.


© St. Petersburg Times, published July 7, 2000

Michael O'Shaughnessy stood in the darkness on the deck of a trawler in Havana Harbor and offered a prayer.

"May our souls be baptized by the blue water of the Gulf Stream," he said. "And may we be better men for it."

With that, the 43-year-old former college football player, businessman and self-professed prophet of paddleboarding jumped into the black water, climbed aboard an 18-foot piece of fiberglass and pointed the bow north.

"I didn't want to paddle behind the boat because the diesel fumes would make me sick," he said. "So I got out in front and told them to keep the spotlights off me. I took a bearing on the North Star and just started paddling toward Key West."

As O'Shaughnessy moved along in the darkness, his unlimited-class paddleboard powered only by the strokes of his hands, he thought about sharks.

"They have been dumping garbage in the water there for 500 years, so the sharks know where to go for a free meal," he said. "As I moved along, I could see fins cutting through the water ahead of me."

Tired, alone and sick with the flu, O'Shaughnessy remembered that a world-record great white shark once was caught off the Cuban coast. His lightweight paddleboard would be no match for such a beast, so he tried to block the thought. Then a full moon peaked above the Havana skyline, and the soft light comforted him.

He knew then that this time, they would make it.

Five days earlier, O'Shaughnessy and 13 other world-class athletes left Key West hoping to make history by being the first men to paddle 112 miles across the Gulf Stream, Ernest Hemingway's "Big Blue River."

The sport of paddleboarding reflects the actions of watermen of ancient Polynesia, who paddled wooden boards across vast tracks of open ocean and, when the spirits called them, stood up and rode the crafts to the beach.

Duke Kahahamoku, known as the father of surfing, and Gene "Tarzan" Smith helped popularize the sport in the 1930s. Then the American Red Cross discovered the paddleboard's usefulness, and lifesaving agencies around the world adopted it as a rescue craft.

It didn't take long before lifeguards started racing the boards and a new sport was born. Today, the Catalina Classic, a 32-mile struggle across the Pacific from Catalina Island to Manhattan Beach, is considered the "granddaddy" of paddleboard races. And while most of the world's paddleboarders live in Southern California, the sport is making great inroads in the Sunshine State thanks to O'Shaughnessy, a native of Winter Park.

"Nobody had ever tried to paddle to Cuba before," he said. "So I figured, why not? What better way to bring attention to the sport?"

O'Shaughnessy assembled three teams of paddlers, 14 men in all, and three weeks ago set out from Key West in 6-foot seas. The Florida Straits are notorious for their ferocity when the wind blows one way and the Gulf Stream current flows the other. Twenty-two hours into the crossing, the paddlers hit the heart of the Big Blue.

"Everybody was seasick. The seas were getting worse. And we had one guy who got knocked off his board by who knows what," O'Shaughnessy said. "It was 3:30 a.m., and we were going nowhere. That's when the boat captain pulled the plug."

The paddlers climbed back on board and headed for Havana.

"People weren't happy," O'Shaughnessy said. "There was a lot of money invested, and it seemed like we had failed."

The paddlers nursed their wounds in Havana for a few days. Many were still sick from a combination of the flu and long hours of inhaling diesel fumes. Then O'Shaughnessy and some others decided to try again.

"I figured we could do it with eight guys, no less than six," he said. "In the end, four agreed to go, myself included."

So they set off at 1:30 a.m. O'Shaughnessy, who organized the expedition, took the first leg and paddled until 5:30 a.m. Then the others -- Derek Levy, Mike Lee and Jeff Horn, all of Southern California -- took their turns.

Now, the current with them, the progress was steady. Midmorning, they picked up an unexpected companion, a 40-foot sperm whale. By late afternoon, they had made Sand Key, 7 miles from Key West. It looked like they would make Mallory Square by sunset.

At that point, O'Shaughnessy asked the support crew -- the lookouts (shark watchers) and film crew that had come along to document the trip -- to each paddle a mile. "I wanted everybody to feel like they participated," he said.

Then, a little more than 19 hours after they began, O'Shaughnessy and his teammates paddled the last stretch into Key West and arrived just as the crowd had gathered to watch the sun go down.

"Somebody asked me where we were paddling from," he said. "I told them Cuba."

A few clapped, but there were disbelievers. "Yeah, right," one man said. "And I'm Fidel Castro."

O'Shaughnessy just smiled. He had nothing left to prove.

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