NHL Trade Deadline: Ranking every team’s worst ever trade

12: New York Islanders

If you want to know why Mike Milbury is the worst hockey mind out there, first try and listen to one of his segments without wanting to punch a hole through your TV, and then look at this trade. Milbury’s time as the general manager of the Islanders was as bad as the condition of the fan that fell victim to his shoe, and this trade, which helped build Ottawa into a Cup contender, perhaps demonstrates that best.

It’s a wonder what Milbury saw in Alexei Yashin that he would offer a second overall pick and Zdeno Chara. Maybe because Yashin was a second overall pick himself it only made sense, plus his 94-point season made him a Hart nominee back in 1998-99. However, he had a real attitude problem and drove the Senators brass crazy with his multiple contract holdouts and his massive ego. So when Milbury came along offering a trade and the money he was asking for, Sens management must have been over the moon and were probably doing several backflips.

Chara, who became a franchise defenseman in Boston, developed into that with Ottawa. His point totals went from 24 to 46 in one season and he was deployed regularly on the power play. It wasn’t luck that Jason Spezza fell to second overall, either. He was a highly touted prospect whom the Senators wasted no time in drafting as soon as they acquired the pick. He, Alfredsson, and Dany Heatley were a fearsome offensive trio that went on a Cup run that came up just short, and even when the All-Star left, Spezza and Alfredsson still formed a tremendous one-two punch.

In Long Island, Yashin was a disaster from the start. Milbury signed him to a 10-year, $87 million deal rendering him untradeable, which they would immediately regret. His production declined severely to the point where his contract was bought out. Like Kovalchuk, the team was forced to pay someone not on their roster – $2.2 million over eight years – which severely affected their cap. It was only last season that the Islanders stopped paying Yashin.

That Chara and Spezza are still playing in the NHL while Yashin is not – although not officially until last year – means that the Islanders were big-time losers. If there’s any solace they can take from this, it’s that they might not have been bad enough to land John Tavares had this deal not gone through.

Next: 11: Chicago Blackhawks