Who is the greatest America’s Cup skipper of all time?

Published on June 16th, 2017

Who is the greatest America’s Cup skipper of all time? As with other sports, making a fair comparison between athletes from different eras is almost impossible. But it always makes for a stirring debate and is a great excuse to reflect on some of the heroes of our sport.

Most Cup historians would agree that Charlie Barr, Dennis Conner and Russell Coutts have to be in the conversation for greatest America’s Cup skipper of all time. And if Jimmy Spithill were to win the 35th America’s Cup, it would be hard to deny his place there as well.

Dennis Conner
© LV Media Centre/Gilles Martin Raget

To casual fans of the sport, Dennis Conner probably remains the most famous America’s Cup skipper in history. A ticker-tape parade in New York and a photo on the cover of Time Magazine will do that for a fellow.

Conner won the America’s Cup four times, three times as skipper (1980, 1987, 1988). But he is arguably more famous for losing it – in 1983, he became the first American skipper to lose the America’s Cup, ending a 132-year winning streak. Had he stopped there, after the loss to Australia, he would be infamous: a great sailor forever linked to a terrible loss.

But Conner’s competitive drive was ferocious and his redemption story is a powerful one. He assembled a tremendous team for the 1987 challenge and won the Cup back, bringing it all the way to the White House and presenting it to President Ronald Reagan.

Conner is recognized as pioneering a professional, full-time, approach to America’s Cup campaigning and noted for his meticulous preparation. His record as a skipper in the America’s Cup is 13 wins against 5 losses.

Russell Coutts (left) and Dean Barker
© Moet & Chandon/Franck Socha

Russell Coutts, in contrast, has an unblemished record in the Cup. He has won the trophy five times, including three consecutive times as a skipper (1995, 2000, 2003), with a 14-0 won/loss mark. Overall, Coutts has won the America’s Cup for three countries – New Zealand, Switzerland, and the USA.

Coutts perfected the game Conner initiated. A Russell Coutts team was immaculately prepared to race. Nothing was left to chance. The boat would be the fastest on the water, the crew work would set the standard, and Coutts and his afterguard executed the playbook better than anyone else.

As his record shows, he was dominant on the water. His 14 wins make him the winningest skipper in America’s Cup history. And he could be sitting on 15 wins. But in the 2000 America’s Cup, in a selfless act of leadership, he stepped off the boat for the final race and handed the helm to his understudy, Dean Barker, to finish the job.

The historical figure to whom Coutts is often compared is Charlie Barr, was also undefeated in three editions of the America’s Cup.

A diminutive Scotsman, Barr won the Cup in 1899, 1901 and 1903, compiling a 9-0 record in those matches. Conner wouldn’t best his record for 84 years, nor Coutts for nearly a century.

Barr was known for aggressive starts, training his crew to execute flawlessly, and an encyclopedic knowledge of the racing rules, which he used to his tactical advantage.

In that, and more, Barr and Jimmy Spithill share some traits.

Like Barr, the Australian Spithill was an foreigner to the USA who first raced for a challenger, before taking up command of American campaigns.

Spithill became the youngest skipper in America’s Cup history with Young Australia in the 1999 Louis Vuitton Cup. He then sailed for the USA and Italy before Coutts recruited him to join BMW Oracle Racing following the 2007 Cup.

He has already won the Cup twice, both times in extraordinary circumstances.

In 2010, Spithill skippered USA17, a trimaran that measured 90 foot on the waterline, with a 90 foot beam, and incredibly, the largest wing ever built in history.

In the match against Alinghi’s giant catamaran, Spithill won 2-0. At 30, he had become the youngest skipper in history to win the Cup.

In 2013, he led his team to perhaps the greatest comeback in all of sport. Down 1-8 on the scoreline and facing match point day after day, Spithill and his crew won 8 consecutive races over Emirates Team New Zealand to defend the Cup 9-8. Factoring in a 2 point penalty, Spithill actually won 11 races in the 34th America’s Cup.

Spithill’s record now sits at 13-8 in America’s Cup matches. Two more wins would give him more victories on the water than Coutts. A win in the match this summer would see him skippering the same team to three consecutive Match wins, something not seen in the Cup since the 1930s.

Given the breadth of his accomplishments – winning on a 90-foot trimaran (2010) and the first foiling catamaran, the AC72 (2013) – Jimmy Spithill is already in the conversation for greatest America’s Cup skipper in history.

A victory in 2017 in Bermuda, would make it 20 race wins, and three matches in a row, and should remove any doubt about his place at the pinnacle of America’s Cup achievement.


America’s Cup Match (June 17 to 28; may end earlier): The final stage of the 35th America’s Cup will see Jimmy Spithill’s Oracle Team USA lining up against Peter Burling’s Emirates Team New Zealand, with the winner to be the first team to claim seven points. However, the caveat is how the Defender, which won the Qualifiers held on May 26-June 3, will begin the series with a one point advantage. As the rules detail, the Challenger will carry a one point disadvantage (ie, minus 1), meaning they will need to win eight races to take the trophy whereas the Defender need only win seven races.

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Source: ACEA

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