8 NHL Trades Still Haunting Teams Years Later

Lyle Fitzsimmons@@fitzbitzFeatured ColumnistDecember 29, 2020

8 NHL Trades Still Haunting Teams Years Later

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    Michael Dwyer/Associated Press

    Bad trades.

    They're the gifts that keep on giving...sort of.

    In fact, fans of every team in any sport can probably concoct a list of deals—some certainly longer than others—that still make them shudder, no matter how long it's been since the transaction went public.

    Don't believe us?

    Ask a pre-2000s Boston Red Sox fan about Babe Ruth, question a 1970s Milwaukee Bucks fan about Kareem Abdul-Jabbar or simply whisper the name Herschel Walker to a Minnesota Vikings fan from the early 1990s.

    And then be prepared to duck.

    Still, hockey has an inglorious collection all to itself.

    Some of the greatest players in NHL history were bundled up and shipped during their prime years, including the one and only Wayne Gretzky, whose move from Edmonton to Los Angeles in 1988 effectively began another era of league expansion while starting the clock ticking on the end of a dynasty in northern Alberta.

    That one came 75 days after the Oilers won their fourth Stanley Cup in five seasons.

    They've won exactly one more in 32 years since.

    To honor that paradigm-shifting deal, the B/R hockey glitterati got together to compile a list of trades that are still haunting teams years after they were made. But rather than simply rehashing cringeworthy horrors of generations past, we established a ground rule that players involved had to still be active or just recently retired—unless there was a particularly compelling reason to reach back even further.

    Take a look at our collection and feel free to talk out your own team's angst in the comments section. This is a safe space, hockey friends.

Honorable Mention: Mark Messier to New York for 3 Players

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    Ron Frehm/Associated Press

    Sorry, Edmonton Oilers fans.

    But while many lists of hockey's worst deals rank the Gretzky-to-Los Angeles disaster as the cream of the crop, we contend that the copper-and-blue dynasty actually ended three years later with this abomination.

    It was then, on Oct. 4, 1991, to be exact, that Mark Messier was sent to the New York Rangers for...wait for it... Bernie Nicholls, Steven Rice and Louie DeBrusk.


    Lest anyone forget, though No. 99 was traded in August 1988, the Oilers made the playoffs the following spring, won their fifth Stanley Cup in 1990 and made the league's final four again in the 1991 playoffs before losing to the Minnesota North Stars.

    Messier, though, was increasingly unhappy and held out prior to the 1991-92 season, forcing the team's hand on a transaction that gutted its heart and soul. Edmonton, on the strength of Esa Tikkanen and muscle memory, made the final four one last time in the 1992 playoffs before a four-year postseason drought.

    Prior to the Messier trade, the franchise had never missed the playoffs.

    And while an entire generation of fans has been born since the Moose last played for them, the haunting has continued to the present day for the Oilers, who've won exactly eight playoff series and zero titles in the subsequent 29 years, including 18 seasons in which they missed the tournament entirely.

    The aforementioned Nicholls, Rice and DeBrusk combined for 159 points in 417 games with Edmonton.

    Messier, on the other hand, helped the Rangers to a Presidents' Trophy and was the league's MVP in his first season and ended a 54-year Cup drought as an encore in 1994. Ironically, alongside him for the parade were ex-Oilers Adam Graves, Kevin Lowe, Jeff Beukeboom, Glenn Anderson, Craig MacTavish and Tikkanen.

    Did we mention ouch?

8. Artemi Panarin to Columbus for Brandon Saad

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    Jamie Sabau/NHLI via Getty Images

    OK, let's bring this to the present.

    The Chicago Blackhawks were a Cup-winning machine in the century's second decade, skating laps with the trophy after the 2009-10, 2012-13 and 2014-15 seasons.

    Winger Brandon Saad took part in the latter two of those parades, netting nine goals across 46 games in the title runs before the team sent him to the Columbus Blue Jackets rather than lose him via free agency.

    Saad had his best (31) and second-best (24) goal-scoring outputs across two seasons in central Ohio, enticing Chicago to bring him back to the fold to regain the championship vibe.

    Problem was, the cost to regain his services included one Artemi Panarin, who'd been named the league's Rookie of the Year and put up 30 and 31 goals in his first two seasons with the Blackhawks.

    And while Saad was serviceable in Chicago stint No. 2, scoring 62 goals across three seasons, Panarin lifted his game even higher, netting 55 goals in two years with Columbus before signing with the New York Rangers and earning a Hart Trophy nomination for a season that yielded 32 goals and 95 points in just 69 games.

    Ironically, Saad was on the move again this offseason and will begin the 2021 schedule with the Colorado Avalanche after a trade that's already been panned by Blackhawks followers.

7. Sergei Bobrovsky to Columbus for 3 Draft Picks

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    Paul Bereswill/Getty Images

    Ah, to be a Philadelphia Flyers fan.

    If you're old enough, you remember the Broad Street Bullies of the 1970s roughhousing their way to consecutive Stanley Cups in 1974 and 1975.

    Since then, well...perhaps it's good the city has other sports teams.

    The Flyers have typically been competitive, but they haven't replicated a championship parade down Broad Street, instead losing in the final round in 1976, 1980, 1985, 1987, 1997 and 2010.

    A frequent lament across many of those years was shaky goaltending, though the team looked set for a while after grabbing undrafted free agent Sergei Bobrovsky.

    Then 22, the lanky Russian was the youngest goalie in franchise history to win a season-opening game and ultimately posted 28 wins and a .915 save percentage in his rookie season of 2010-11. But he was 0-2 with an .877 save percentage over six games in the subsequent playoffs, prompting the team to sign free agent Ilya Bryzgalov and relegate Bobrovsky to backup duty.

    He was dealt to the Columbus Blue Jackets the following summer in exchange for second- and fourth-round picks in the 2012 draft and a fourth-round pick in 2013. 

    Suffice to say the change of scenery worked out OK. For him anyway.

    A 2.00 goals-against average and a .932 save percentage fueled him to a Vezina Trophy in his initial season with the Blue Jackets, a feat he replicated after winning a career-best 41 games for them in 2016-17. In fact, he won 213 games for Columbus across seven seasons before signing a seven-year, $70 million free-agent deal with the Florida Panthers prior to the 2019-20 season.

    As for the Flyers, they selected Anthony Stolarz and Taylor Leier in 2012, and the 2013 pick was subsequently dealt to the Los Angeles Kings, who used it to take Justin Auger.

    Also a goalie, Stolarz had six wins in 19 games across two seasons with Philadelphia and appeared in one game with the Anaheim Ducks in 2019-20. Leier, a winger, had two goals in 55 games with the Flyers in parts of three seasons and most recently played in the AHL last season. As for Auger, he posted zero points in two games with the Kings and is now under contract with the Florida Everblades of the ECHL.

    Bryzgalov, incidentally, lasted all of two seasons in Philadelphia and was bought out of the final seven years of his nine-year contract. He won 13 more NHL games with three teams before exiting the league for good in 2015.

6. Roberto Luongo to Florida for Mark Parrish and Oleg Kvasha

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    Mike Strobe/NHLI via Getty Images

    It's been 20 years, and it still doesn't look good.

    Goaltender Roberto Luongo was a first-round draft pick in 1997 and reached the New York Islanders net two years later, initially backing up Felix Potvin before taking over the starting job at age 20 and finishing his rookie season with a respectable .904 save percentage across 24 games.

    It appeared he'd be a cornerstone for a franchise eager to return to its glory days.

    Until he wasn't.

    Selecting first overall in the 2000 draft, Islanders general manager Mike Milbury decided to shake things up by taking teenager Rick DiPietro—making him the first goalie ever picked No. 1—and dealing Luongo to the Florida Panthers with 21-year-old center Olli Jokinen for two-year veterans Mark Parrish and Oleg Kvasha.

    All Luongo did was develop into one of the league's best goaltenders and arguably the tops in the history of two franchises—the Panthers and Vancouver Canucks—thanks to a career in which he played more than 1,000 games, won 489 of them and racked up a 2.52 goals-against average and .919 save percentage.

    Jokinen wasn't bad, either, recording four seasons of 30-plus goals with the Panthers on the way to 321 for his career across 1,231 games with 10 teams.

    Parrish and Kvasha were hardly embarrassing with the former netting a career-best 30 goals for the Islanders in 2001-02 and the latter scoring 60 times in five seasons with the team. But their impacts pale in comparison to Luongo and Jokinen.  

    As does that of the enigmatic and brittle DiPietro, who wound up winning 359 fewer games than Luongo through his final NHL appearance in the 2012-13 season. Adding financial insult to chronic injury, he was bought out of the last eight years of his final contract after that season, meaning the Islanders still owe him $1.5 million annually through 2029.

5. Tuukka Rask to Boston for Andrew Raycroft

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    Claus Andersen/Getty Images

    Here's a nugget for the Toronto Maple Leafs fans in the house: Tuukka Rask is the all-time leader in wins among goaltenders drafted by the franchise, but every single one of those wins has been with the Boston Bruins.

    Historians will recall that the Leafs barely missed the playoffs in the 2005-06 season after the league returned from a lockout that blew up the 2004-05 schedule. And those same historians might suggest that goaltending was at fault thanks to iffy season-long performances from veterans Ed Belfour (3.29 goals-against average in 49 games) and Mikael Tellqvist (3.13 GAA in 25 games).

    So the Toronto brass was in a deal-making mood and on the lookout for a proven netminding commodity.

    They found it in the form of Boston's Andrew Raycroft, who'd been the league's Rookie of the Year in the season preceding the lockout and, though coming off his own shaky performance in 2005-06, was still just 26 years old and presumably had quality playing days still ahead.

    The cost was then-teenage prospect Rask, who the Maple Leafs had plucked in the first round of the 2005 draft but wasn't presumed ready to contribute on a team focused on winning immediately.


    Though he initially shared time with veteran Tim Thomas, it was clear Rask was a long-term star in the making when he posted league bests in goals-against average (1.97) and save percentage (.931) while winning 22 games in 45 appearances with the Bruins in 2009-10.

    A Stanley Cup title followed a season later, and Rask broke through for a Vezina Trophy after a 2013-14 season in which he won 36 games and had a league-high seven shutouts. He's compiled 291 wins and 50 shutouts through the end of the 2019-20 season and enters this season still No. 1 on the Boston depth chart.

    Oh, and as for Raycroft, he was gone from Toronto after two seasons and played his last NHL game for the Dallas Stars in 2011-12. It was later revealed the Bruins were planning to release him outright, which would have made him available to the Leafs with no compensation—and no Vezina winner—necessary. 

4. Joe Thornton to San Jose for Marco Sturm, Wayne Primeau and Brad Stuart

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    Fred Kfoury III/Icon Sportswire via Getty Images

    Alas, the Boston Bruins taketh. And they sometimes get taken, too.

    Though the franchise with the spoked-wheel B logo made out when it comes to Rask, it didn't turn out quite the same way when it comes to another veteran who'll still be playing when pucks drop next month.

    Joe Thornton was Boston's No. 1 overall pick in 1997, played seven full seasons with the Bruins and was 23 games into his eighth when then-general manager Mike O'Connell pulled the trigger on a deal that sent him to the San Jose Sharks in exchange for forwards Marco Sturm and Wayne Primeau and defenseman Brad Stuart.

    It was a shake-up-the-rosters move for both the Bruins and Sharks, who'd struggled at the outset of the 2005-06 season. The Bruins, though, continued to plummet and missed the playoffs at the end of the season while the Sharks finished second in their division and reached the second round of the postseason.

    Thornton was an instant mainstay in northern California, winning the league's MVP award and scoring title at the end of the initial season and helping the Sharks make the playoffs 13 times in 15 seasons.

    He was among the franchise's all-time leaders in goals (fourth), assists (first) and points (second) when he finally left in the offseason following 2019-20, signing a one-year deal with the Toronto Maple Leafs.

    Sturm had four seasons with 20 or more goals with the Bruins before leaving via trade to the Los Angeles Kings, while neither Primeau nor Stuart lasted two years in Boston. In fact, both were again traded, this time to the Calgary Flames, for Andrew Ference and Chuck Kobasew in February 2007.

3. Patrick Sharp to Chicago for Matt Ellison and a Draft Pick

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    Len Redkoles/NHLI via Getty Images

    The Philadelphia Flyers have traded bigger-name modern-day players.

    But when a guy you sent away beats you to win a Stanley Cup, that's going to leave a mark.

    Patrick Sharp was a third-round pick of the Flyers in 2001 and was coming along nicely enough across parts of three seasons in the NHL, scoring 10 goals in 66 games with Philadelphia before a decision was made midway through the 2005-06 season to let him go. He was dealt to the Chicago Blackhawks with teammate Eric Meloche for winger Matt Ellison and a third-round pick in the 2006 draft.

    Sharp scored nine goals in 50 games with his new team that season, netted 20 more in his first opportunity as a full-timer the following campaign and broke out with 36 goals across 80 games in 2007-08.

    Two seasons later, he had 11 goals and 11 assists in 22 playoff games as the Blackhawks won their first title in 49 years, beating the Flyers in six games. He was the MVP of the NHL All-Star Game the following season, eclipsed 30 goals again in both 2010-11 and 2011-12 and won two more Stanley Cups in 2013 and 2015, sandwiched around an Olympic gold medal in 2014.

    The good news? Meloche never played a game in the NHL after leaving Philadelphia.

    The bad news? Ellison played exactly seven games with the Flyers before heading off to play professionally in the KHL, and Philadelphia traded away the draft pick that came with him.

2. Tyler Seguin to Dallas for 4 Players

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    Glenn James/NHLI via Getty Images

    Ladies and gentlemen, it's Peter Chiarelli time.

    Though history will indeed recall the Ontario native as a Stanley Cup-winning general manager with the Boston Bruins in 2011, it'll also recall him as the executive who ultimately traded both the first and second overall picks from the 2010 NHL draft.

    It's the dealing of the second pick from that draft, Tyler Seguin, that gets him his spot here. (Though ask an Edmonton Oilers fan about his subsequent trade of that year's No. 1 selection, Taylor Hall, and you'll surely get a memorable reaction, too.)

    At any rate, Seguin was picked by the Bruins and paid instant dividends, scoring 11 goals as a rookie in his initial regular season and adding seven points over 13 playoff games in Boston's run to the Stanley Cup. He followed with 29 goals in his second season and again helped the Bruins reach the Cup final after season No. 3, though they were beaten in six games by the Chicago Blackhawks.

    It wasn't enough for Chiarelli, however, who sent his budding 21-year-old star to the Dallas Stars, along with depth player Rich Peverley and minor-leaguer Ryan Button, in a trade for Loui Eriksson, Reilly Smith, Joe Morrow and Matt Fraser.

    Seguin, to say the least, is no longer budding.

    He's reached 30 goals five times and 40 goals once over seven seasons in Texas and scored 13 more playoff points as the Stars reached the Stanley Cup Final against the Tampa Bay Lightning following the 2019-20 season. And while Peverley is best known for a rink-side cardiac incident that ended his playing career in 2014 and Button never played an NHL game, it's little consolation for Bruins fans.

    Eriksson played only three seasons in Boston before bolting as a free agent, Smith was there for two seasons before a trade sent him to the Florida Panthers, Morrow had nine points in 65 nondescript games in black and gold, and Fraser had five goals in 38 games before he was waived and claimed by Edmonton.

1. Zdeno Chara and a 1st-Round Pick (Jason Spezza) to Ottawa for Alexei Yashin

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    Andre Ringuette/NHLI via Getty Images

    OK, we'll see your Peter Chiarelli and raise you a Mike Milbury.

    Already a party to a deal on this list that saw him choose Rick DiPietro over Roberto Luongo, the ex-New York Islanders general manager did his fanbase even dirtier with the 2001 draft-day swap that sent Zdeno Chara, role player Bill Muckalt and a first-round pick to the Ottawa Senators in exchange for forward Alexei Yashin.

    Chara, for those unaware, was only 231 games into a career that's since seen him evolve into one of the NHL's all-time-steadiest defensemen.

    In fact, through the end of the 2019-20 season, he's played more than 1,500 games, scored more than 200 goals, taken part in six NHL All-Star Games and won both a Norris Trophy and a Stanley Cup.

    As for that first-round pick, the Senators used it to select Jason Spezza at No. 2 overall. He has since played more than 1,100 games in the league while scoring 341 goals and suiting up in two All-Star Games.

    And while it's true that Muckalt logged just 78 more games in the league after the trade, the damage was done to the Islanders in myriad ways in the form of Yashin, who signed a 10-year contract worth $87.5 million.

    His point production declined from his Ottawa days in each of his first three seasons with New York, and the Senators, with Chara and Spezza, beat the Islanders in the first round of the 2002-03 playoffs.

    Yashin's points went from 66 to 50 in the two seasons that followed the 2004-05 lockout, and he was bought out of the final five years of the deal after 2006-07 for a hefty $17.63 million that was parsed out annually through the end of the 2014-15 season.


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