On this day in Islanders history: Rick DiPietro signs a 15-year contract to cap off a bizarre summer on Long Island

Can you believe it's been 16 years since the New York Islanders signed G Rick DiPietro to a landmark 15-year contract? The mega-deal, signed on September 12, 2006, was supposed to pay the brash and confident netminder $4.5 million each season until 2021, totaling $67.5M. But after a long string of injuries and bad luck derailed his career, the team bought out DiPietro's contract on July 3, 2013, resulting in the team paying the 2008 NHL All-Star $1.5M annually through the 2028-29 season.

The deal was the largest under the NHL's 2005 NHL collective bargaining agreement. The only contract that came close was when Lou Lamoriello attempted to sign Ilya Kovalchuk to a 17-year contract that was later nullified and ruled improper by the league resulting in a punishment being handed out to the New Jersey Devils for salary cap circumvention.

The former No. 1 pick in the 2000 NHL Entry Draft was a week away from turning 25 and fresh off a breakout season when he became the youngest goaltender in franchise history to win 30 games. DiPietro finished the season with a 30-24-5 record, a 3.02 GAA, and a .900 Save %. It was later reported that the Isles first attempted to sign DiPietro to the same contract the previous September but were discouraged by the NHL. A year later, it happened during one of the strangest summers an NHL franchise have ever had.

"In all of our discussions with Rick, he made it clear that he wanted to be an Islander for the rest of his career, But it was of equal importance to Rick that we work out a deal that would allow us to continue to build a Stanley Cup contender for years to come. This deal is great news for our franchise and our fans."

- Garth Snow

The press conference and headline-grabbing announcement before the start of the 2006-07 season was the culmination of an eventful off-season for the Isles that summer. Ted Nolan, who had not coached in the league since 1997, was named head coach and owner Charles Wang hired ex-Rangers Stanley Cup-winning GM Neil Smith to replace Mike Milbury. On the same day of Nolan's hiring, former Islander Pat LaFontaine was announced as a special advisor.

Smith was dismissed after six weeks on the job after failing to meet owner Charles Wang's expectations of a front office by committee. "I knew it would get worse because when you know it's wrong, it doesn't work," Wang said. "You feel it and you've got to correct it."

What's remarkable in retrospect is how active and effective Smith was in his six weeks. He signed 30-goal scorer Mike Sillinger and veteran hard-hitting defenseman Brendan Witt to three-year deals along with defenseman Tom Poti and forwards Chris Simon and Andy Hilbert. All were contributors for the Islanders, who made the playoffs on the last day of the 2006-07 season.

Backup goaltender Garth Snow was named General Manager as Smith's replacement, and the learning-on-the-job 36-year-old would sign his former teammate to the record-breaking deal two months later. "I guess it's pretty beneficial to be a goaltender on LongIsland right now," DiPietro quipped at the press conference.

"Clubs are free to make their own decisions" within the rules, NHL deputy commissioner Bill Daly said. "Time will tell whether this will be a good decision or a bad one for the Islanders." It didn't take much time to find out. After playing in 63 and 62 games in the two seasons following the contract, DiPietro would only play in 50 games over the next five seasons due to injuries after being bought out. But the memory of the contract (and the contract itself) lives on.