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The two Stanley Cup championships in the early 1990s were the high point of the Pittsburgh Penguins’ existence. They were also the origin of problems that nearly drove the hockey franchise out of that existence. By decade’s end, the Penguins filed for bankruptcy, an embarrassing development that led to the most impressive power play of Mario Lemieux’s brilliant career.

Lemieux assured the Penguins’ future by making a risky deal that just paid off to the tune of $360 million.

A young Mario Lemieux led the Pittsburgh Penguins to the top

NHL legend Mario Lemieux talks to the media during the Scotiabank NHL100 Classic at Lansdowne Park on Dec. 16, 2017, in Ottawa, Canada. | Minas Panagiotakis/NHLI via Getty Images
NHL legend Mario Lemieux talks to the media during the Scotiabank NHL100 Classic at Lansdowne Park on Dec. 16, 2017, in Ottawa, Canada. | Minas Panagiotakis/NHLI via Getty Images

The Pittsburgh Penguins chose wisely by making Montreal native Mario Lemieux the No. 1 selection of the 1984 NFL Draft. His 100-point debut season earned Lemieux the Calder Trophy, and he reached triple digits nine more times in a 17-season career.

Injuries marred the second half of his career, but the 6-foot-4 center finished with 690 goals and 1,033 assists in 915 regular-season contests. On top of that, he rolled up 76 goals and 96 assists in 107 playoff games. The high point came at the conclusion of the postseason in 1991 and ’92 as the Penguins hoisted a pair of Stanley Cups.

The success came at a price. Hockey lacked the lucrative TV contracts of the other major team sports, and the Penguins’ ownership spent its way into more than $100 million in debt. One short-term remedy was to convince several NHL players, including Lemieux, to restructure their contracts and accept deferred salaries. Though Pittsburgh returned to the playoffs every year through 2001, the Penguins only made it as far as the conference finals twice.

Mario Lemieux made $360 million with one save

The seven-year, $42 million extension Mario Lemieux signed with the Pittsburgh Penguins shortly after helping them to their second Stanley Cup turned into mostly deferred money in order to help the team. When the owners filed for bankruptcy in November 1998, Lemieux became the largest secured creditor, according to sports and finance reporter Joe Pompliano.

Lemieux made a prescient move by offering to convert the majority of the $32.5 million Penguins owed him into a 25% share of the franchise. A year later, Lemieux became the president and managing partner.

“The bankruptcy process was a great learning experience, but it was a tough process to go through,” Lemieux told The Washington Post upon the bankruptcy court accepting his bid. “There was a lot of frustration day-to-day. I surrounded myself with smart people.

“You’re going to see a lot more players in the future getting involved in their sports,” he said. “It’s healthy. That’s good for the sport.”

The Post-Gazette reported in August 2005 that the Penguins had succeeded in repaying all of their creditors. By that time, Lemieux had begun accumulating a larger ownership stake. That stake turned into a $360 million windfall, most of it pure profit from a wise investment.

Mario Lemieux is cashing in most of his Penguins chips

The Pittsburgh Penguins announced on Nov. 29 that Fenway Sports Group intended to acquire controlling interest of the NHL team, a proposal that the league’s Board of Governors quickly approved. FSG, which John Henry runs, also owns the Boston Red Sox, Fenway Park, the Liverpool club in the English Premier League, Roush Fenway Keselowski Racing, and part of the NESN sports channel.

Lemieux reportedly will maintain a small ownership stake and remain influential in the club’s oversight, but he benefits greatly from the sale. At an assumed valuation of $900 million once all the paperwork is complete, Lemieux walks away with $360 million, according to Joe Pompliano.

That makes his initial deal with the Penguins the savviest play on deferred cash since Bobby Bonilla said goodbye to the New York Mets.

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