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NHL draft-day trade disasters: Remembering some of the worst deals since 2000

The NHL draft is one of the most stressful times for a GM. One bad move can set your franchise back for years. Let's take a look at some of the most memorable draft-day trade disasters since 2000, serving as a warning for teams looking to improve their roster this weekend in Vancouver.

The NHL draft is all about setting yourself up for the future, but it has the potential to set your franchise back, too.

Part of what makes draft weekend so much fun is that teams will try to make a big splash, not just on the draft board, but on the trade market as well. Teams with a good prospect base may move their first-round pick in order to improve their roster immediately as a way of getting ahead of the free-agent rush that begins on July 1.

But it's also a time where you can do a lot of damage to your organization. All draft picks are a gamble: you've scouted them, you've analyzed them, but you don't know how they're going to do as pros. Moving a pick to get an established player can be rewarding but can disfigure your team's success just as easily. With that in mind, let's take a look at some of the most memorable draft-day trade disasters since 2000, serving as a warning for teams looking to improve their roster this weekend in Vancouver:

June 24, 2000
NY Islanders got: Mark Parrish and Oleg Kvasha
Florida got: Roberto Luongo and Olli Jokinen

The deal: Oh boy, this one takes the cake. The Islanders planned on taking Rick DiPietro with the first overall pick in 2000, meaning Luongo, the team's top pick in 1997 (fourth overall) was on the way out. Jokinen was unproven at the time with just 42 points over the next two years. In Parrish and Kvasha, the Islanders were getting two veterans whom they hoped would help spark the lineup.

The verdict: Luongo is currently the active leader in wins by a goalie and still plays in Florida to this day after a mostly successful stint in Vancouver. Jokinen, meanwhile, has the most points in Panthers history with 419 in 567 games. Parrish had a couple of good years in New York, but Kvasha was a bust, recording a career-high 51 points in 2003-04 before going overseas in 2006, never to return to the NHL. Good thing then-Isles GM Mike Millbury wouldn't make another terrible draft-day deal, right? Well, not for another 366 days, at least.

June 23, 2001
NY Islanders got:
Alexei Yashin
Ottawa got: Bill Muckalt, Zdeno Chara, No. 2 overall pick (Jason Spezza)

The deal: Yashin wasn't bad by any stretch of the imagination in New York -- he never recorded fewer than 66 points in a full season and was easily one of the most skilled players to bolt for pre-KHL Russia when he did. But it came at the cost of moving Chara, a future Hockey Hall of Famer, even if he did relocate to Boston a few years later. Spezza recorded 80-plus points on four occasions, joining Daniel Alfredsson as the only Senators player to do so that many times.

The verdict: Ottawa sent away the franchise's best player at the time, but acquired a one-of-a-kind behemoth defenseman in Chara, and a future star in Spezza, who would go on to become one of the Senators' most dominant forces for a decade. Yashin was bought out five years later. Just imagine how good the Islanders could have been in the turn of the century if they had Luongo, Spezza, Dany Heatley and Chara at their disposal.

June 24, 2006
Toronto got:
Andrew Raycroft
Boston got: Tuukka Rask

The deal: A Calder Trophy winner for an unproven European prospect? It was a risky deal for Boston to make at the time, even if Raycroft had a tough 2005-06 season. Surely, he was capable of bouncing back, right? That was Toronto's job to figure out.

The verdict: Three Stanley Cup final appearances by Rask later and, yeah, it backfired on the Leafs. Raycroft played an incredible 72 games for the Leafs in 2006-07 as the team just missed out on the playoffs. But that was it for him as a starter: he'd bounce around the league for a few years before ending up in Italy and Sweden to finish off his career. Rask, on the other hand, has done OK for himself.

June 22, 2007
Toronto got: Vesa Toskala and Mark Bell
San Jose got: 13th overall pick (eventually became Logan Couture at No. 9), 44th overall pick (traded to St. Louis) and a fourth-round pick in 2009

The deal: Raycroft wasn't the answer in Toronto, so the Leafs had to surrender another chunk of the team's future to address its goaltending issues. Toronto obtained Toskala, one of the better backup goalies in the league, in an effort to challenge Raycroft for starts, and Bell was a big forward needing a fresh start after a bad year in California.

The verdict: Just ignoring two of the picks Toronto sent to San Jose, it was a complete disaster for the Leafs. Bell was suspended before even playing a game after pleading no contest to drunk driving and hit-and-run charges from an incident when he was still with the Sharks, recording just 10 points in 35 games in 2007-08. Toskala played three tough seasons in Toronto that were plagued by a highlight reel of bad goals before finishing his career as a forward in Thailand. In San Jose, Couture has posted at least 50 points in all seven of the years in which he played at least 60 games and is one of the best playoff performers over the past decade. Speaking of the playoffs, Toronto hasn't won a series since either of these deals.

June 26, 2015
Edmonton got:
 Griffin Reinhart
NY Islanders got: No. 16 overall pick (Mathew Barzal) and No. 33 overall pick (eventually became Anthony Beauvillier at No. 28)

The deal: For once, the Islanders actually won a trade. Edmonton needed an upgrade at defense – that hasn't changed in the past four years – and got Reinhart, a promising youngster, in a deal for two picks. The Islanders got a bit crafty, turning the 33rd overall pick into No. 28 before the end of the first round.

The verdict: Reinhart, who spent his junior career playing with the WHL's Edmonton Oil Kings, skated in just 29 contests with the Oilers before spending most of his two years with the club in the AHL. These days, he can be found patrolling the Chicago Wolves' blueline having not played in the NHL since April 2016. Barzal is one of New York's best players in a couple of decades and Beauvillier has made a good career out of being a depth scoring winger on Long Island.

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