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Connolly surprised the yachting world by winning a prestigious race series in the waters off Florida in 1968

Perry Connolly, right, in his Royal Canadian Yacht Club blazer, accepting a trophy.

Perry Connolly made a fortune building Holiday Inn hotels in Ontario, which allowed him to indulge his passion as a racing skipper.

It was his famous challenge to long-time friend George Cuthbertson that led to the commissioning of Red Jacket, a speedy sloop that surprised the yachting world by winning a prestigious race series in the waters off Florida in 1968.

Mr. Connolly later became operations director for a syndicate responsible for Canada's entry to compete in the 1987 America's Cup, a challenge that ended in defeat and with acrimony.

In retirement, he became a notable volunteer at a hospital in Portland, Ore., before moving to Sidney, near Victoria, B.C., where he was well known as a volunteer at the local aquarium.

Mr. Connolly died of lung cancer in hospital on Sept. 29, at the age of 90. His death preceded that of Mr. Cuthbertson, who died at home in Toronto of a heart attack, at the age of 88, by four days.

In 1965, Mr. Connolly asked his friend to design "the meanest, hungriest 40-foot sloop afloat."

So Mr. Cuthbertson devised an innovative hull of end-grain balsa between two fibreglass skins, which he claimed was the first of its kind anywhere in the world.

Mr. Connolly's Sailboat Red Jacket

The clever elimination of weight coupled with a large and tall sail made the craft exceptionally fast.

The sailboat was constructed by Erich Bruckmann, a German-born master boat builder who would later become one of the founders of Mr. Cuthbertson's fabled C&C Yachts. It was christened by Mr. Connolly's daughter, Shelagh, and launched in 1966. The sloop was named Red Jacket, after the White Star Line clipper ship that set a speed record for crossing the Atlantic on her maiden voyage in 1854.

Red Jacket proved an immediate sensation, finishing second in its first competition before winning 11 of the next 12 races in his first season on Lake Ontario.

It was a dark-horse entry in 1967 in the Southern Ocean Racing Conference series known as the "conch-shell-and-flying-fish circuit" held in the waters off Florida and the Bahamas.

Red Jacket defeated more than 100 crack yachts in its first saltwater race from St. Petersburg to Venice, along Florida's Gulf Coast. A tactical mistake in the Miami-Nassau Race cost the crew the overall championship that year.

Mr. Connolly returned to Florida the next year, skippering a crew including Gordon Fisher, the future president of Southam newspapers. Red Jacket won the overall title over such contenders as Bolero, a 73-foot yawl owned by billboard mogul and future CNN founder Ted (The Mouth of the South) Turner, and Inferno, another yacht designed by Mr. Cuthbertson and built by Mr. Bruckmann, owned by Jim McHugh, of Chicago. Mr. Connolly became the first foreigner to win the series.

In 1969, Mr. Connolly shared skipper duties with Mr. Fisher aboard Manitou, also designed by Mr. Cuthbertson, as they sailed to a Canada's Cup victory over Niagara, representing the Cleveland Yachting Club, in a series held in the waters off Toronto.

Mr. Connolly was director of operations for Canada II's challenge for the America's Cup in 1987. The crew failed to qualify for the semifinals of the Louis Vuitton Cup, which serves as an elimination race to determine the challenger to the America's Cup holder.

George Cassian, George Cuthbertson and Perry Connolly appear in an undated photo.

Perry Roe Connolly was born in Vancouver on June 24, 1927. He was the first of five children born to the former Mary Roe, a homemaker, and Stuart Connolly, a construction contractor. The family later moved to Ontario, where the boy indulged his passion for sailing at both the Port Credit Yacht Club and the Royal Canadian Yacht Club in Toronto. He met Mr. Cuthbertson while both were still teenagers.

Mr. Connolly studied construction techniques at the Ryerson Institute of Technology (now Ryerson University) in Toronto. His P.R. Connolly Construction built hotels for Commonwealth Holiday Inn, including buildings in Toronto and Winnipeg. The firm was an early adopter of using prefabricated concrete units.

Mr. Connolly died at Saanich Peninsula Hospital outside Victoria, B.C. He leaves a son, Brian Connolly, of Portland, Ore., and daughters Shelagh McKinley, of Windsor, Ont., and Patty Connolly, of Boca Raton, Fla. His marriage to the former Pat Davidson ended in divorce. He also leaves a sister, a brother, and five grandchildren. He was predeceased by a brother.

His considerable volunteer contributions included more than 10,000 hours at Kaiser Sunnyside Medical Center in Clackamas, Ore., southeast of Portland. After moving to Vancouver Island, he became a familiar face as a volunteer with the Shaw Centre for the Salish Sea, a non-profit aquarium in Sidney, B.C.

Late in life, mobility difficulties ended his ability to board watercraft. Instead, he purchased a radio-controlled Laser sailboat, which he operated at a marina, teaching young people the rules of racing.