Rick Dipietro has perhaps the saddest story in the NHL. In just four short years after the fraudulent purchase of the Islanders by John Spano, Islander fans were not ready for the newest saga of pain and suffering that the number one pick in the 2000 draft would bring in the next 13 years.
The Islanders went into the 2000 NHL draft with both the first and fifth picks in the first round. With talent like Dany Heatley and Marian Gaborik available at the number one spot, the team decided to go in another direction. A goalie out of Boston University stole the show as the first goalie to be selected number one.
With the new era beginning on Long Island, the Islanders decided to trade their major goaltenders in the system. Roberto Luongo was packaged to Florida and Kevin Weeks was shipped to Tampa Bay. This meant that Dipietro would be the Islanders number one immediately.
Due to a groin injury in September of that year, Dipietro played the majority of the season with the Islanders IHL affiliate, the Chicago Wolves. His first game was on Jan. 27 against the cup contending Sabres, where he allowed two goals in the Islanders loss but put up an assist on the Islanders only goal. The Islanders finished last in the Eastern Conference that season but the future looked bright for the young netminder.
Until the injuries piled up.
Just before the season which his injuries started to come together, the Islanders wanted to lock down their future all-star goalie and did so with a monster contract worth $67.5 million over the span of 15 years. This is the contract most fans of any team will point to as an example of perhaps the worst in NHL history.
From the beginning of his career right up to the end, injuries plagued his once promising potential. His first injury that put him down the path to the hockey graveyard was a mild concussion after a collision against Canadien’s forward Steve Begin in March of 2007. Only a few short weeks later he suffered another concussion against the Rangers which caused him to miss the remainder of the season.
Exactly a year later in March 2008, Dipietro had his first of two surgeries as he underwent a hip surgery followed by a knee surgery. This made him miss the 27 games of the 2008-2009 regular season. Following his recovery on Dec. 26, Dipietro made his return in a 4-1 victory over the Toronto Maple Leafs. In the following game however, Dipietro reported swelling his his knee and missed the remaining 41 games.
In that offseason of 2009, the Islanders took John Tavares first overall in the NHL Draft in Montreal. The new “savior” was here while the previous one just underwent another surgery on his swollen knee. This caused Dipietro to miss an additional 27 games into the 2009-10 season.
Knee problems continued to haunt Dipietro into the last stretch of the 2009-10 season. Another reported swelling in March 2010 cause Dipietro to miss the last 12 games of the season. This string of injuries caused the Islanders to bring in durable goalie Dwayne Roloson from the Oilers on a two-year deal worth $5 million, a small contract compared to the one Dipietro was getting paid.
In Feb. of 2013, after a disappointing stint in the AHL’s Bridgeport Sound Tigers, Dipietro in an interview talked about committing suicide. Even though it was cleared up by the media, comments like that shoved the Islanders’ management to buy-out the eight remaining years of his contract on July 1 of 2013.
The 13-year saga was over. But not quite.
His $1.5 million dollar buy-out will be paid until 2029.

David Lazar