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Bryan Berard met Phil Kenner when he was a 17-year-old defence phenom fresh from Woonsocket, Rhode Island, playing junior hockey in Detroit. Kenner was a 25-year-old financial advisor, and a buddy of NHL veteran Joe Juneau.

Berard trusted the laid-back, curly-haired Kenner. He had been Juneau’s college hockey teammate in Troy, N.Y., and best man at Juneau’s wedding.

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As Berard’s career took off — he was a first-round draft pick in 1995, and won the Calder Trophy two years later with the New York Islanders as the NHL’s top rookie — he began investing with Kenner; he was one of a number of hockey players who became clients and friends of the Boston-based advisor.

Over the course of his 15-year career, the hockey star would give Kenner millions of dollars for what Berard thought were Hawaiian real estate developments and a lucrative debit card business.

But when his career was winding down — he retired from the NHL in 2008, with 76 goals and 247 assists in 619 career games, including 102 as a Toronto Maple Leaf — Berard began to question why his $3-million worth of investments had yet to pay off.