Charles Wang purchased the New York Islanders in 2000 for an estimated $190 million U.S. (Mary Altaffer/Associated Press)

In the grand tradition of larger-than-life New York sports impresarios, Charles Wang is doing it his way.

The mercurial owner of the New York Islanders has pushed noted meddlers like George Steinbrenner and James Dolen to the newspaper back pages with a series of off-season moves that a generous observer would describe as controversial, and a realistic one would call bizarre.

Wang's latest head-scratcher was unveiled earlier this week when during a news conference in Uniondale, N.Y., the self-described risk-taker announced he'd persuaded promising but unproven goalie Rick DiPietro to accept a jaw-dropping 15-year contract extension.

The deal, which pays DiPietro $67.5 million US, is the longest ever doled out in NHL history and is believed to be the second longest in North American major pro sports history after the 25-year, $25-million deal Magic Johnson inked with the Los Angeles Lakers in 1981.

DiPietro will be 40 when the contact expires in 2022.

"You have to have a commitment to who you're working with," said Wang, who made billions as a software developer.

"I've done this all my business career. Now I'm doing it in sports and everybody is like, 'Oh my God. How could he do that?'"

He's right; pretty much everybody is like that. The Globe and Mail headline the next morning accused Wang of "Long Island Lunacy," while one unnamed NHL executive called the Islanders' owner "insane."

Readers canvassed by CBC.ca almost universally said "what the…?" when asked their opinion on the deal.

The prevailing belief is that if DiPietro doesn't continue to develop - or gets hurt - the contact will hang like an albatross around the franchise's neck.

Critics question what team, in the supposedly cost-conscious NHL, would take on a guaranteed contract of that magnitude. The deal, they argue, renders DiPietro untradeable.

"Clubs are free to make their own decisions," said Bill Daly, NHL commissioner Gary Bettman's right-hand man.

"Time will tell whether this will be a good decision or a bad one for the Islanders."

Dubious decisions

Questionable decisions are nothing new for Wang's Islanders. For years, Wang employed Mike Milbury. Dubbed "Mad Mike," he was widely considered one of the worst general managers in the NHL.

In four NHL seasons, Rick DiPietro is 58-62-13 with a 2.85 goals-against average in 143 games. (John Bazemore/Canadian Press)

Among the Wang-Milbury boondoggles: signing underachieving Alexei Yashin to a 10-year, $87.5 million deal, trading away star goaltender Roberto Luongo for a negligible return, and taking DiPietro with the first pick in the 2000 NHL entry draft ahead of future stars Dany Heatley and Marian Gaborik.

And, according to reports, Milbury was also responsible for planting the idea of signing DiPietro to a long-term deal in Wang's head.

Given that track record, it may be no surprise that Milbury no longer serves as the Islanders' general manager. Earlier this year he was promoted by Wang.

Finding a replacement for Milbury was another adventure for Wang. Initially, front-office veteran Neil Smith was given the job, but he lasted a mere 40 days with the team, fired because he couldn't operate in Wang's "front office by committee," which also counts coach Ted Nolan, Bryan Trottier and Ken Morrow as advisors. Milbury's opinion is also believed to still hold some sway with Wang.

Wang replaced Smith – the man who built the 1993 New York Rangers into Stanley Cup champions – with Garth Snow, the Islanders' backup goalie.

In an interview with the New York Times shortly after Snow's hiring, Wang, who at one time reportedly considered employing sumo wrestlers as goaltenders, admitted his management style was "unorthodox."

Unorthodox business man

"I've built businesses all my life and I look at it a little differently perhaps," Wang told the newspaper. ''…sometimes we do unorthodox things with the idea that maybe this is a better way, a different way.''

Wang attributes his throw-caution-to-the-wind business approach to his mother.

"My nature seems to be that I like to try this, I like to try that," he said in an interview with the Asian business website Asia Gate.

"My mother's the more curious one; she's always wanting to try this, try that. I think that sense of adventure is from her side."

Born in Shanghai in 1944, Wang immigrated to the United States in the 1950s with his parents and two brothers to escape communism. In pre-revolutionary China, the Wangs enjoyed a life of privilege – Wang's father, Kenneth, was a judge in the highest court in the land – but in America they struggled to make do, living in a modest home in Queens, N.Y.

Wang's father taught at St. John's University while his mother, Mary, was a librarian. Charles worked odd jobs to augment the family's income.

In 1966, Wang was wrapping up an unimpressive scholastic career at Queens College when he answered a help-wanted ad for a computer programmer at Columbia University. Despite never having used a computer, he landed the job.

Wang spent the next several years in various dead-end computer jobs before joining Computer Associates, at the time a small Swiss-based software company.

Wang did so well selling computer software in the U.S. that he, along with older brother Tony, bought Computer Associates and took it public, growing CA into one of the biggest software companies in the world, at times rivalling Microsoft, IBM and Oracle.

While most hockey writers describe Wang as "quirky" or "eccentric," business journalists used other adjectives to describe the 62-year-old. Wang developed a reputation as a ruthless corporate raider, who devoured smaller companies and spit out their bones.

According to a 2000 article in Business Weekly, Wang assembled CA from the parts of some 200 companies. After purchasing these companies he'd strip them of top executives and many of their chief programmers.

When asked about the takeovers and purges, Wang responded: "This dragon has only one head.''

Wang's colleagues, on the other hand, paint a picture of a fair man who treats his employees well and demands loyalty in return.

"We both have this blind loyalty issue,'' said Wang's protege, Sanjay Kumar told Business Weekly. "It's beyond words. It's till death do us part."

Wang left CA in 2002, but it didn't come without some controversy. At the time of his retirement, CA sales were slumping and the company was being investigated for questionable accounting practices. The case, which centred on Kumar, is still ongoing.

Since that time, Wang has spent a good chunk of his time working on real estate deals and running his arena football team, the New York Dragons, and the Islanders, which he purchased in 2000 estimated $190 million US.

When he bought the Islanders, Wang admitted he knew little about the NHL, but was reading Hockey for Dummies.

"A lot of this is new to me, but it will be run like any good business."