As a child, he learned to sail on Casco Bay. Now he’s ranked No. 1 in the world

Falmouth High graduate Chris Poole, 34, recently became the first skipper to win every match race at the prestigious Congressional Cup regatta in California.

When Chris Poole was learning how to sail on the choppy, unpredictable waters of Casco Bay, he decorated his bedroom wall in Falmouth with pictures of famous America’s Cup skippers.

Two weeks ago, Poole, 34, did something that even the legends of competitive sailing have never accomplished. He skippered his five-person Riptide Racing crew to an unprecedented feat – winning all 24 match races – en route to victory in the 58th Congressional Cup regatta at the Long Beach Yacht Club in California.

The Congressional Cup, held this year from April 18-22, is one of the world’s most prestigious match race sailing events. The match race format pits two teams against each other on identical boats. The idea is the best sailors win, not the priciest boat. At the Congressional Cup, the 10 skippers used Long Beach Yacht Club’s fleet of Catalina 37s, a classic 37-foot monohull yacht design.

“It’s definitely the highlight of my sailing career so far. I’m sure there are going to be a few higher ones, but this one was easily the top right now,” Poole said in a telephone interview from Westport, Connecticut, where he lives with his wife, Alicia Martorella, and their 3-year-old daughter, Aurora.

Poole found early success after taking up sailing at age 10 in Maine, and along the way learned to curb a temper that gave him “a reputation of being a bit hotheaded.” He has been a professional sailor for seven years, but his career has rocketed in the past 18 months. Today, Poole is ranked No. 1 in the world among match race skippers – and dreams of sailing in the America’s Cup.

“To go 24-0, to be perfect in a World Match Racing Tour event, which is a feeder to the America’s Cup, it’s never been done before,” he said. “Not at the Congressional Cup and I don’t believe ever at any Grade 1 event, which is the top grading a match race can have.”

Past winners of the event include several America’s Cup sailors, including Americans Ed Baird and Ken Read and New Zealand’s Dean Barker – a trio of early inspirations for Poole – as well as America’s Cup winners Ted Turner and Dennis Conner. Four-time America’s Cup winner Russell Coutts of New Zealand, another of Poole’s sailing heroes, never won the Congressional Cup. And no one before Poole went through the regatta unbeaten.

Falmouth native Chris Poole, far right, skippered his team to the Congressional Cup victory on April 22. The crew members are, from left, Matt Cornwell, Luke Payne, tactician Joachim Ashenbrenner, Mal Parker, and Bernardo Freitas. Ian Roman/WMRT

“It is as strong an event as there is in match racing,” said Bill Simon, a sailing umpire from Annapolis, Maryland. Simon has organized, directed, and umpired top match races in the United States for more than a decade, giving him a front-row seat to watch Poole move up the ranks.

“He’s beating everyone who shows up, and he did it convincingly this year,” Simon said.

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