5 worst contracts signed in New York Islanders history feat. Rick DiPietro

By Cole Shelton

Modified Jul 23, 2024 18:36 GMT

Established in 1972, the New York Islanders have made some great moves but also some poor ones. The Islanders have occasionally been handicapped by some poor free-agent signings, limiting their success.

That said, here are five of the worst contracts in franchise history.

5 worst contracts signed in New York Islanders history

#1, Rick DiPietro

Rick DiPietro was the New York Islanders' franchise goalie, as he was selected first overall in the 2000 NHL draft. He had success but, in 2006, New York gave him a historic contract.

The Islanders signed him to a 15-year, $67.5 million contract. It was a stunning deal, but after signing the contract, DiPietro dealt with a plethora of injuries as he skated in just 50 games over the next five seasons and was bought out in 2013 with eight years remaining on his contract.

DiPietro's deal is considered to be one of the worst in NHL history.

#2, Andrew Ladd

In 2016, the New York Islanders were looking to add some leadership to their room. In free agency, New York lost Kyle Okopso and Frans Nielsen who were their leaders, so the Islanders went out and signed Ladd.

Ladd was a key part of the Hurricanes that won the Stanley Cup in 2006 and the Blackhawks team that won the Cup in 2010.

Ladd was given a seven-year, $38.5 million contract but was hampered by injuries, as he skated in 181 games, recording 39 goals and 33 assists for 72 points.

#3, Alexei Zhitnik

In 2005, the New York Islanders went out and signed defenseman Alexei Zhitnik to a four-year deal. Zhitnik was supposed to help bolster the defense, but that didn't happen.

Zhitnik lasted just 89 games with the Islanders and was traded to Philadelphia.

#4, Chris Simon

Chris Simon signed a one-year deal worth $1 million for the 2006-07 season with the New York Islanders.

Although it was not a long contract, it is what happened to Simon that made the deal so bad. He was suspended 25 games, which carried over to the next season, but the Islanders decided to bring him back. He then purposely stepped on Jarkko Ruutu’s leg, which resulted in a 30-game suspension that ruined his time in the NHL and with the Islanders.

#5, Mikhail Grabovski

Mikhail Grabovski was a solid NHL player with the Toronto Maple Leafs, and in 2014, he signed a four-year, $20 million deal with New York.

However, Grabovski was hampered by injuries as he played just 109 games over two seasons. He only played two of the four years with the Islanders due to the injuries.