When Australia stunned the sailracing world in 1983 by wresting the America’s Cup from the United States after a 132-year winning streak, syndicate backer Alan Bond became a national hero Down Under, and a holiday was declared to honor the victory.

Fourteen years later, the high-flying businessman entered Karnet Prison Farm for what would be a four-year incarceration after pleading guilty to financial fraud to the tune of $1.2 billion (Australian). Bond died June 5 at the age of 77 following complications during open-heart surgery, and a national debate over the legacy of this intensely polarizing personality was renewed.

“He was a huge influence on the sport of sailing, and while he is best remembered for the success of the America’s Cup campaign, he loved international racing, particularly the Admiral’s Cup, and many ocean-racing campaigns,” Yachting Australia president Matt Allen says in a statement.

Allen recalled sailing aboard one of Bond’s yachts as a 20-year-old, saying, “I clearly remember he was one of the most positive people I’ve ever met, with an incredible determination and strong will to succeed.”

The New York Yacht Club, which represented Dennis Conner’s defending syndicate — the first ever to lose the Cup — issued a terse, one-sentence statement when Bond died: “The New York Yacht Club acknowledges with regret the passing of Australian yachtsman Alan Bond, a persistent four-time challenger and 1983 winner of the America’s Cup.”

Bond was born in London in 1938 and immigrated with his parents to his adopted homeland at age 12. According to Australian media reports, he was a wayward youth who had minor brushes with the law and dropped out of school when he was 14.

He became a brash and, by some accounts, ruthless businessman who built and nearly lost several fortunes before scripting the biggest financial scandal and bankruptcy in Australian history. Even after his prison stint, “Bondy,” as his friends and admirers called him, returned with great success to the business world.

He was passionate about fine art — he bought Vincent van Gogh’s renowned painting Irises for $54 million — as well as sailing. “Alan had a long sailing career and raised the profile of the sport in Australia and around the world over many decades,” says Allen. “At a time when some of Australia’s most successful skippers took part, two Admiral’s Cup campaigns beckoned for Alan, his first in 1973 with Apollo II and then again in 1981 with Apollo V.”

After three failed attempts to win sailing’s top prize, the syndicate bankrolled by Bond made global headlines when Australia II, with its revolutionary winged keel and skippered by John Bertrand, bested Conner’s Liberty over seven races off Newport, Rhode Island. Grant Simmer, general manager of Oracle Team USA — the syndicate that currently holds the Cup — was a young navigator on the victorious crew.

“I met Alan through John Bertrand. We had been sailing on one of Alan’s boats called Apollo 5, which we took to the Admiral’s Cup,” Simmer recalls in a tribute posted on the America’s Cup website. “Alan sailed on the boat with us. We did the [Sydney-Hobart] race with him on that boat. And then it was Alan who pushed to have me as navigator for Australia II. I hadn’t been a navigator before that.”

Simmer says the bold move was evidence that Bond was a risk-taker both in business and on the water. “I think he had a vision that he wanted to have a younger team and bring in some fresh ideas. You can get stale in these campaigns if you stay with the same group,” Simmer says.

Bond’s private life also was not without drama. He was married twice and had four children with his first wife. (They divorced in 1992.) But his daughter Susanne died in 2000 at 41 of what was ruled an accidental prescription drug overdose. His second wife committed suicide in 2012 after battling clinical depression.

“[He] was also a great family man. I know how proud he was of all of his children,” Simmer says. “Alan was certainly one of a kind.”

This article originally appeared in the August 2015 issue.