Wearing the winner’s Crimson Jacket, Chris Poole takes a good look at the Congressional Cup trophy after he and his crew sailed to the prestigious match race championship on April 22 in Long Beach, Calif. Ian Roman/WMRT

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.


The second of four children of Susan Poole of Falmouth and Parker Poole III, who lives in Portland, Chris Poole had familial connections to maritime activities. His grandfather (and later his uncles) owned Union Wharf, the historic pier on Portland’s waterfront that was sold by the Poole family in 2021. The family had no sailing experience, however, until Susan signed up Chris’ older brother, Parker, for a Portland Junior Yacht Club learn-to-sail program.

The next year, it was Chris’ turn to take the program, but there was no space in the beginner’s class. His mother told the instructors she thought Chris could handle the intermediate class. Chris wasn’t so sure when his mother dropped him off on the first day.


“I asked what I was supposed to do. She just said, ‘Act like you know what you’re doing.’ Three weeks later, the coaches went to my mom and said they wanted me to sail in some sort of junior Olympics event,” Chris Poole said.

Using a club-owned Optimist dinghy, the 10-year-old placed second in a field of 40 youth sailors.

A racer was born.

“I liked being in control of the boat and trying to master elements you had no control over,” Poole said. “You had to have foresight to figure out what the wind was going to do, and use currents to your advantage.”

Through his early teens, Poole raced around New England with a small group of young sailors from Portland Yacht Club that included Leigh Palmer’s daughter Libby and son Alan. Leigh Palmer was the first woman to be the PYC Commodore, has sailed herself since 1968, and is still actively involved in the high school-age SailMaine program as a member of the board.

At age 12, Chris Poole prepares to compete in the 2002 Optimist Atlantic Coast Championships in Bellport, New York. Photo courtesy of Leigh Palmer

Racing the bathtub-like Optimist boats, the 11- to-14-year-old sailors challenged each other to improve, Leigh Palmer said.


“They egged each other on and really competed,” Palmer said.

At the time, Poole wasn’t the fastest of the Portland Yacht Club racers, Palmer said. Her son usually led the way.

“I’m so proud of where Chris has ended up,” she said. “He can go to any regatta and he can sail any boat, and he’s going to be a competitor, a top opponent. And that he can win at the Congressional Cup, with 24 unbeaten matches, it’s just unheard of.”

After graduating from Falmouth High in 2007, Poole went to Maine Maritime Academy in Castine, where he competed on the sailing team. Poole was expanding his sailing experiences to offshore races in bigger yachts, often working on the crew for Portland Yacht Club member Rich Stevenson in the Gulf of Maine Offshore Racing Association events.

“He would come out on the boat, and boy, he was laser-focused, always energetic,” said Stevenson, who now lives on Vinalhaven. “He was very enthusiastic and wanted to win. So he stood out that way.”

Stevenson said Poole’s competitive streak and sometimes abrasive confidence was on full display during a Monhegan Island Race, a roughly 140-mile overnight offshore event. On board with skipper Stevenson and Poole was the late Merle Hallett, who had won the Monhegan and many other offshore races.


At some point, Poole challenged Hallett, the navigator, about a decision. It led to a lengthy, at times heated, discussion about tactics. Stevenson says he wondered if he should separate the two but …

“Merle loved it. And that was pretty amazing to see this younger gentleman arguing with a Maine sailing legend, and now Chris is a sailing legend in his own right,” Stevenson said. “My rule was always, ‘If Merle says go there, we go there.’ They were challenging each other. The result was we got every trophy we could get for the class we were in.”

Chris Poole speaks after he and his crew won the 58th Congressional Cup at Long Beach Yacht Club in April. Poole is ranked No. 1 in the world among match race skippers. Ian Roman/WMRT


After graduating from Maine Maritime in 2012, Poole moved to Oyster Bay, New York, home of Oakcliff Sailing, a coaching and training center formed in 2010, and the Seawanhaka Corinthian Yacht Club. Poole was confident his sailing future was in match races, and in Oyster Bay, he could compete every week.

“It’s the only sailing discipline where it’s not the equipment, it’s the sailors,” Poole said. “Every event provides identical boats, and to win you have to have the best sailors, not the fastest boat or the best tech.

“Another reason I like the tour is we sail a different boat at every single event,” he continued. “You can’t be good at just one discipline or a particular boat.”


For several years, Poole’s progress was relatively slow. While the match race circuit allows sailors to compete without owning a boat, there are still expenses for travel, lodging, and meals – expenses incurred while taking time off from a job.

“For the earlier years, it was a lot of cutting your teeth and trying to win prize money and trying to basically get by,” Poole said.

If things didn’t go well, Poole was prone to angry outbursts. And he had never been shy about speaking his mind.

“He was a little bit of a hothead growing up, but he was the middle of three brothers,” Palmer said. “What do you expect?”

Simon, who was the race director at Oakcliff Sailing for many years, said Poole has grown into a more mature, controlled sailor over the past 10 years. That’s made him a better competitor, Simon said.

The new cool, calm approach is also saving Poole money. Teams have to supply a credit card that gets charged immediately if they damage a boat.


“Yeah, I had a reputation of being a bit hotheaded and overly aggressive at times, and I’ve lost a couple of hull damage deposits,” Poole said. “It’s just part of the learning curve. What do they say? You have to break a few eggs to make an omelet.”

Chris Poole and crew compete during the Congressional Cup regatta at Long Beach Yacht Club in April. Poole’s team won all 24 of its match races – an unprecedented feat at the event. Ian Roman/WMRT

Poole generates some of the money needed to run his successful team through sponsorships and fundraising. Winning regattas helps, too. The first prize at the Congressional Cup was $20,000. The majority of Riptide Racing’s financial backing comes from Hunt and Betsy Lawrence of Oyster Bay, who founded Oakcliff Sailing to help support young sailors. Initially, Poole received support from the Oakcliff Foundation. In recent years, the Lawrences have provided additional backing for Poole’s efforts.

The increased support allowed Poole to build a stable team of crew members with more focused training. Better results followed.


The 2022 season was a breakout year. Poole competed in eight events that counted toward his world ranking. He won three, placed second twice – including at the World Match Race Tour final in Sydney, Australia – and had two-thirds and a fourth. He won two of the four regattas and the overall championship in the Grand Slam Series of U.S. Grade 2 match races.

“We started treating our team and our campaign like an America’s Cup program, with that level of focus and how we prepare, train, coach ourselves,” Poole said.


Having former match race competitor Joachim Aschenbrenner of Denmark join the Riptide team as its tactician was a key step. The tactician determines how to get ahead and stay ahead of the other boat. That leaves Poole to focus on the nuances of wind and current and make the steering and sail adjustments to put the boat on the fastest groove around the 15-to-20-minute course.

In Long Beach, Poole, Aschenbrenner, bowman Matt Cornwell, and trimmer Mal Parker, along with Luke Payne and Bernardo Freitas, were untouchable. After going 18-0 in the double round-robin against the other nine boats, they beat 2022 World Match Race Tour champion Nick Egnot-Johnson of New Zealand, 3-0, in the semifinals and did the same to Jeppe Borch of Denmark, ranked No. 2 in the world, in the final. Six-time World Match Race champion Ian Williams of Great Britain, the reigning and five-time Congressional Cup champ was the other semifinalist.

Skippers and their crews race on identical 37-foot yachts, Catalina 37s, during the Congressional Cup regatta at Long Beach Yacht Club. The race format is designed to let the best sailors win, not the priciest boat. Ian Roman/WMRT

By the end of this racing season, Poole is looking to keep his No. 1 world ranking, win the World Match Racing Tour, and win the World Match Race Championship finals, Dec. 12-17, in Shenzhen, China.

Then there is the peak of the international sailing world: the America’s Cup.

Contested every three or four years, America’s Cup racing has become an event driven by high-tech innovations, with boats that use water foils to lift the hull above the water. To bring a team to the competition requires – by Poole’s estimate – about $150 million. Poole hopes he might be able to catch on with one of the five challenging teams looking to supplant current cup holder Emirates Team New Zealand, which will defend its title in October 2024 in Barcelona, Spain.

“I would love to be a part of America’s Cup. It’s been a dream of mine ever since I got into sailing,” Poole said. “I would love to have my own campaign, but $150 million is a big ask. The immediate goal is to be involved in the next cycle in some way in Barcelona.”

The foundational sailing skills Poole learned in Casco Bay have already taken him around the globe.

“I’ve always known I can be a very fast helmsman from my early days in Casco Bay,” Poole said. “Not to brag, but I’m the No. 1-ranked match racer in the world. When I’m allowed to just sail the boat and be the helmsman, I’m kind of showing I can be a world-class helmsman and be that quick all the time. Hopefully I can do that someday in the America’s Cup.”

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