The Greatest Characters Ever To Contest The America’s Cup

John Cox Stevens (1785–1857)

John Cox Stevens was a wealthy New York businessman, sportsman and the first Commodore of the New York Yacht Club in 1844. A passionate advocate of yacht racing since a young boy growing up on the banks of the Hudson River, he owned the pilot-schooner America and skippered her to victory around the Isle of Wight in 1851. His decision to donate the RYS £100 Cup to the New York Yacht Club created what became ‘America’s Cup.’ Stevens believed the trophy should be held as a perpetual international challenge, laying the foundations for the world’s oldest, continually contested, international sporting competition. He died in 1857, never knowing the extraordinary legacy his vision would create.

George L. Schuyler (1811–1890)

George Lee Schuyler’s foresight ensured the long-term future of the America’s Cup. Following John Cox Stevens’ death, Schuyler re-drafted and executed the Deed of Gift in 1857, formally donating the America’s Cup to the New York Yacht Club as a perpetual challenge cup for “friendly competition between foreign countries.” His carefully crafted legal framework established the principles that still govern the competition today, making him one of the most influential figures in the Cup’s history. Schuyler successfully defended the Deed through numerous legal and sporting challenges, ensuring the trophy remained a genuine international contest rather than a private possession. Although he never raced for the Cup himself, his vision and stewardship laid the constitutional foundations upon which every subsequent America’s Cup has been contested.

Susan Henn (1853–1911)

Susan Matilda Cunninghame-Graham Henn was a pioneering Scottish yachtswoman and the first recorded woman to compete in the America’s Cup. Using a substantial inheritance, she commissioned and financed the steel cutter Galatea, which challenged for the Cup in 1886, and sailed her across the Atlantic rather than travelling by steamship. During the Match, when her husband, Lieutenant William Henn, became unwell, Susan took command of the yacht for part of the contest, making her the first woman to command an America’s Cup yacht. Although Galatea was defeated by Mayflower, her seamanship earned widespread admiration at a time when women were largely excluded from competitive sailing.

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Nathaniel G. Herreshoff (1848–1938)

Nathaniel Greene Herreshoff, known as the “Wizard of Bristol,” was the most influential yacht designer of the nineteenth-century. Designing for the Herreshoff Manufacturing Company, he created five consecutive successful defenders: Vigilant (1893), Defender (1895), Columbia (1899 and 1901), and the extraordinary Reliance (1903).  Herreshoff pioneered lightweight steel construction, advanced hull forms, balanced rudders and sophisticated sail plans, bringing scientific engineering to yacht design decades ahead of his contemporaries.

Harold S. Vanderbilt (1884–1970)

Harold Stirling Vanderbilt was heir to the Vanderbilt fortune and one of the finest amateur helmsmen in sailing history. He successfully defended the America’s Cup three times, skippering Enterprise (1930), Rainbow (1934) and the ‘superboat’ Ranger (1937) – the latter two being financed by himself. Vanderbilt combined exceptional tactical ability with meticulous preparation and helped establish America’s dominance during the magnificent J-Class era – often called the ‘Golden Era.’ He is regarded as one of the greatest helmsmen ever to contest the Cup.

Hope Goddard Iselin (1868–1970)

Hope Goddard Iselin was one of the most influential women in the early history of the America’s Cup and a prominent figure in New York high society. Married to banker and yachtsman C. Oliver Iselin, she became a familiar presence aboard America’s Cup defenders during the late nineteenth and early twentieth centuries, accompanying campaigns at a time when women were rarely associated with elite yacht racing. Hope was closely connected with the New York Yacht Club and entertained royalty, industrialists and leading yachtsmen, helping to elevate the America’s Cup’s social prestige during the Gilded Age. Her grace, intelligence and enthusiasm for sailing made her an admired ambassador for the sport, and she remained an enduring symbol of the glamour and international appeal that surrounded the Cup in its formative years. She lived to the remarkable age of 101, spanning almost the entire era from Sir Thomas Lipton’s first challenge to the dawn of the modern America’s Cup.

Sir Thomas Lipton (1848–1931)

Sir Thomas Lipton was the Scottish-born tea merchant who became not only one of Britain’s most famous businessmen but at one point it is thought, the richest man on the planet. Between 1899 and 1930 he mounted five unsuccessful America’s Cup challenges with his ‘Shamrock’ yachts, winning enormous admiration for his sportsmanship and determination. Despite never lifting the America’s Cup, he became one of the Cup’s most beloved figures and helped transform it into a truly international spectacle. His friendship with American competitors strengthened Anglo-American sporting relations. Lipton’s name remains synonymous with gracious defeat and unwavering optimism.

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Sir T.O.M. Sopwith (1888–1989)

Sir Thomas Octave Murdoch Sopwith was a pioneering aviator, industrialist and founder of the Sopwith Aviation Company. A gifted yachtsman, he challenged for the America’s Cup twice with the magnificent J-Class yachts Endeavour (1934) and Endeavour II (1937). His campaigns introduced unprecedented professionalism, engineering excellence and financial commitment to British yacht racing. Although unsuccessful, Endeavour came closer than any British challenger in decades to lifting the Cup. Sopwith is remembered as one of Britain’s greatest sporting entrepreneurs.

Olin Stephens (1908–2008)

Olin Stephens was one of the greatest yacht designers in history, whose influence on the America’s Cup spanned more than half a century. Co-founder of the renowned design firm Sparkman & Stephens, he designed or co-designed no less than eight successful America’s Cup defenders: Ranger (1937 with Starling Burgess) Columbia (1958), Constellation (1964), Intrepid (1967 and 1970), Courageous (1974 and 1977), and Freedom (1980). Stephens combined scientific naval architecture with an intuitive understanding of yacht performance, pioneering the use of tank testing, structural engineering and meticulous performance analysis long before computer modelling became commonplace.

Baron Marcel Bich (1914–1994)

Baron Marcel Bich, the French industrialist and co-founder of the BIC company, brought France to the forefront of the America’s Cup through a series of ambitious challenges between 1970 and 1980. Determined to break the long-standing Anglo-American dominance of the competition, he financed four campaigns with the yachts France (1970), France II (1974), France III (1977) and France III again in 1980. A passionate yachtsman and accomplished helmsman, Bich combined substantial personal investment with a scientific approach to yacht design, helping to advance French naval architecture and campaign organisation. Although he never reached an America’s Cup Match, his commitment laid the foundations for France’s emergence as a serious force in international sailing and inspired future French syndicates.

Ted Turner (1938 – 2026)

Ted Turner was an American media entrepreneur who founded CNN and transformed global television news. A fiercely competitive yachtsman, he skippered Courageous to victory in the 1977 America’s Cup, defeating Australia’s challenge. Renowned for his aggressive tactics and charismatic personality, Turner brought a new level of publicity and celebrity to the event. His success confirmed him as one of the outstanding helmsmen of the 12-Metre era. He later became one of the world’s leading philanthropists and environmental campaigners.

Dennis Conner (1942 –)

Dennis Conner is one of the most influential figures in modern America’s Cup history, earning him the nickname ‘Mr America’s Cup.’ He won the trophy four times and became the first American skipper to lose the Cup in 1983 before winning it back in Fremantle in 1987. Conner revolutionised campaign management by embracing sports science, sponsorship and professional teamwork. He also skippered the controversial catamaran that won the 1988 Deed of Gift Match. Few individuals have shaped the modern Cup more profoundly and his moniker’s of ‘No Excuse to Lose’ and ‘The Commitment to the commitment’ remain true to this day.

Alan Bond (1938–2015)

Alan Bond was an Australian entrepreneur whose determination ended 132 years of American dominance. After launching four successive challenges, Bond’s syndicate finally won the America’s Cup in 1983 with Australia II. Bond’s willingness to invest heavily in technology and recruit the world’s best sailors, designers and sailmakers transformed international yacht racing. Although his later business empire collapsed spectacularly, his sporting achievement remains one of Australia’s greatest victories. His success changed the America’s Cup forevermore and ushered in the modern era.

John Bertrand (1946 –)

John Bertrand is the Australian skipper who led Australia II to its historic America’s Cup victory in 1983. His calm leadership and tactical intelligence helped end the New York Yacht Club’s 132-year winning streak. Bertrand later became an advocate for leadership, teamwork and high performance, drawing on lessons from the campaign in business and education. He has remained an influential voice in Australian sailing for decades. His victory is regarded as one of sport’s greatest upsets and his book ‘Born to Win’ is a must-read for all aspiring America’s Cup team-members.

Ben Lexcen (1936–1988)

Ben Lexcen was the genius, unconventional Australian yacht designer behind Australia II, the winner of the 1983 America’s Cup with a revolutionary winged-keel design that changed the Cup forever.  The keel, and a superlative sail plan, gave Australia II a crucial performance advantage and became one of the most famous innovations in sailing history and broke the New York Yacht Club’s extraordinary 132-year hold on the Cup. A fiercely original thinker who constantly challenged conventional yacht design, Lexcen’s legacy is that of one of the most influential designers in America’s Cup history.

Dawn Riley (1964 –)

Dawn Riley is one of the most accomplished and influential women in America’s Cup history, breaking down barriers in a sport long dominated by men. In 1992 she became the first woman to compete in an America’s Cup Match as a crew member aboard America³, which successfully defended the Cup in San Diego. She later became the first woman to manage an America’s Cup syndicate, leading ‘America True’ in the 2000 America’s Cup campaign in Auckland. Beyond the Cup, Riley has competed in multiple Whitbread Round the World Races and has been a passionate advocate for diversity, leadership and youth development in sailing. Her pioneering career paved the way for greater female participation at the highest level of the sport, culminating in the introduction of the Women’s America’s Cup in 2024 and women on the AC75 yachts in 2027.

Sir Peter Blake (1948–2001)

Sir Peter Blake was New Zealand’s most celebrated yachtsman and one of the greatest sailors of his generation. After crewing on several America’s Cup campaigns, he captained Team New Zealand to consecutive victories in 1995 and 2000, establishing the nation as a sailing superpower. Blake also won the Whitbread Round the World Race and set numerous offshore records. Following his racing career, he devoted himself to global environmental conservation. He was tragically killed by pirates while on an environmental expedition in the Amazon in 2001.

Raul Gardini (1933–1993)

Raul Gardini was the charismatic Italian industrialist who founded the Il Moro di Venezia America’s Cup challenge. His vision and considerable investment elevated Italy into one of the world’s leading sailing nations, culminating in the 1992 Louis Vuitton Cup victory and a place in the America’s Cup Match. Gardini assembled an outstanding international team of designers and sailors while promoting Italian innovation and style. Although Il Moro di Venezia lost to America³, the campaign inspired a generation of Italian sailors. Gardini died in 1993 but left a lasting legacy on Italian sailing at the very pinnacle in the America’s Cup.

Patrizio Bertelli (1946 –)

Patrizio Bertelli is the Italian businessman who transformed Prada into one of the world’s leading luxury brands alongside his wife, Miuccia Prada. A lifelong yachtsman, he founded what is now ‘Luna Rossa’ in 1997 and has led one of the most successful challengers in modern America’s Cup history. Under his leadership, Luna Rossa has won two Louis Vuitton Cups (2000 and 2021) and has consistently pushed technological innovation. Bertelli’s long-term commitment has made Italy one of the Cup’s dominant modern forces. He remains one of the event’s most influential owners.

Ernesto Bertarelli (1965 –)

Ernesto Bertarelli is the Swiss entrepreneur and philanthropist who transformed Alinghi into one of the most successful teams in modern America’s Cup history. After founding the syndicate in 2000, he led Switzerland to a controversial victory at its first attempt in Auckland in 2003, becoming the first team from continental Europe ever to win the America’s Cup. As owner and an active crew member, Bertarelli successfully defended the Cup in Valencia in 2007, helping to stage one of the most commercially successful and internationally attended editions of the event.

Grant Dalton (1957–)

Grant Dalton is a New Zealand round-the-world racer and the current Chief Executive of Emirates Team New Zealand. A veteran of the Whitbread Round the World Race, he has overseen one of the most successful periods in America’s Cup history, winning the trophy in 2017, defending it in 2021 and again in 2024 – the only consistent team to win three in a row. Dalton has championed technological innovation, commercial sustainability and a more global vision for the event, including the move to Barcelona in 2024 and Naples for 2027. Widely respected for his determination and strategic leadership, he has become one of the defining figures of the modern America’s Cup era.