Ranking the Best Offseason NHL Trades Since 2000

Who doesn't like trades?

One team going all-in for the present while another looks to the future. Standout players being sent off for a change of scenery after wearing out welcomes. Or two general managers simply stirring things up.

Doesn't matter why they happen. We're just happy they do.

And lest anyone think the time between the Stanley Cup parade laps and the opening of training camps is a dull, hockey-less glut, remember that many significant moves do occur during the so-called offseason.

Here in 2021, we're looking at you, Jack Eichel.

Anyway, firmly aware of that transactional reality, the B/R hockey writing types set off on a summertime research project to review and ultimately rank the best offseason trades made since 2000.

Of course, "best" is an ambiguous term. A best deal for one team could be recalled as a nightmarish event for another. So we tried to find trades that provided at least some benefit both ways. Or, in some cases, we went with the ones that were so successful in one direction it's impossible to deny them a placing.

Take a look at what we came up with, and drop a line or two in the comments.

As we said, not every deal is a bell-ringer on both sides.

In fact, some are simply hand-wringers.

File this one with the latter category, at least when it comes to the Buffalo Sabres.

Buffalo brought in rugged center Ryan O'Reilly from the Colorado Avalanche as the centerpiece of a deal that included five players and a draft pick, and he signed a seven-year contract extension worth $52.5 million.

He was a 20-goal scorer in each of three seasons with the Sabres but ended the 2017-18 campaign with a media session in which he claimed he had lost his love for the game, among other issues.

Not surprisingly, he was dealt away from his hockey purgatory less than three months later, landing with the St. Louis Blues in exchange for three players and a pair of draft picks.

Sabres fans will be quick to remember that O'Reilly not only hoisted the Stanley Cup and earned the Conn Smythe Trophy at the end of his first season with the Blues, but he also won the Selke Trophy as the league's best two-way forward. He was named the team's captain prior to the 2020-21 season.

Buffalo, meanwhile, has gotten a combined 23 goals in three years from Tage Thompson, Vladimir Sobotka and Patrik Berglund,

Ouch, Western New York. Just ouch.

Where have you gone, Bernie Parent?

For nearly every moment—or at least a lot of the moments—since the Philadelphia Flyers last won the Stanley Cup in 1975, they have been searching for the sort of franchise goaltender who, like Parent, could backstop them to the promised land.

They have had short-term success with a lot of imitators over the years but haven't managed to secure another parade down Broad Street in spite of six subsequent trips to the championship round.

They stumbled on to another possibility upon signing Sergei Bobrovsky to an entry-level contract in 2010 and watching him earn the starting gig to begin the 2010-11 season. He became the youngest goalie in franchise history to win a season-opening game, the first Flyers rookie to win to win his debut since 2004 and wound up with 28 wins and a 2.59 goals-against average in 54 games.

It was a magical time. Until 10 goals allowed in 186 playoff minutes convinced the team that it had to go big-game hunting—signing Ilya Bryzgalov to a nine-year, $51 million deal—to address the issue.

Bobrovsky was relegated to backup status for 2011-12 and appeared in only 29 games before the Flyers dumped him to Columbus for three draft picks, none higher than a second-rounder.

The picks didn't materialize into much, but Bobrovsky quickly became a sensation in middle Ohio, posting a 2.00 goals-against average and a .932 save percentage across 38 games, good enough to earn him the Vezina Trophy as the league's top goalie. He won 30 or more games five times in the subsequent six seasons, including a career-high 41 in 2016-17, before heading to Florida as a free agent in 2019.

Bryzgalov, meanwhile, spent just two seasons in Philadelphia before the team bought out the final seven years on his contract.

When the New York Islanders made Rick DiPietro the first pick in the 2000 draft, it was a big deal.

He was a teenager. He was heading to New York. And he was the first goalie ever taken at No. 1.

But that wasn't the only big deal.

To make room for their precocious youngster, the Islanders blew up their goaltending tandem from the 1999-2000 season, jettisoning both Roberto Luongo and Kevin Weekes in separate deals.

The trade that sent Luongo to the Florida Panthers was particularly memorable because the then-20-year-old blossomed into one of the league's best goalies, posting five shutouts in his initial season with the team and boosting his win total across each of the next four seasons—culminating with 35 wins in 2005-06.

He later won 47 games and helped backstop a push to the Stanley Cup Final in separate seasons with the Vancouver Canucks and ultimately won 489 games, good for fourth in league history.

The Islanders got Mark Parrish and Oleg Kvasha in exchange for Luongo. And though their 169 goals with the team were respectable enough, they don't quite measure up. As for DiPietro, he reached double-digit wins just four times and was bought out of the final eight years of his 15-year contract.

Here's a tip: If you're going to discuss this one with an Edmonton Oilers fan, duck.

Because you're just as likely to get a confrontation as a conversation.

For those who don't recall, Pronger spent one uber-successful season in northern Alberta after arriving to the Oilers in a deal with the St. Louis Blues and signing a five-year, $31.25 contract extension.

He helped the team advance to the Stanley Cup Final in 2006 after qualifying as the eighth seed in the Western Conference, and though they were beaten in a seven-game series by the Carolina Hurricanes, hope sprang eternal for a return to relevance the following season.

Until four days later, that is.

That's when Pronger's agent informed the team that his client had requested a trade because of personal reasons, a suggestion that birthed a thousand rumors before culminating eight days later in a deal that sent Pronger to the Anaheim Ducks for two players and three draft picks.

Pronger got his name on the Cup with the Ducks following that first season in California, while the Oilers plummeted into a decade of darkness and didn't see the playoffs again until 2016-17.

As for the Pronger return, the Oilers got little to no production from forward Joffrey Lupul, some respectable work on bad teams from defenseman Ladislav Smid and turned one of the picks into Jordan Eberle, who was taken in the first round in 2008 and spent seven seasons in Edmonton.

Kudos if you recall that Brent Burns was a first-round draft pick as, wait for it...a right winger.

Now that he's a Norris Trophy winner and multi-time All-Star thanks to performance on the blue line for the San Jose Sharks, it's easy to forget the now-36-year-old arrived to the Minnesota Wild in 2003.

He played parts of seven seasons with the Wild while shuttling back and forth from forward and defense and maxed out at 17 goals and 46 points in 80 games in 2010-11.

A draft day deal in 2011 saw him shipped with a pick from the Wild to the Sharks for two players and a pick. The shifting between positions continued in his early days in San Jose before the Sharks announced he would make a permanent move to defense prior to the 2014-15 season.

And suddenly, a star was born.

Burns was second among NHL defensemen with 60 points in that first season, bumped the number to 75 points the following season while helping the Sharks reach the Stanley Cup Final and both won the Norris and was nominated for the Ted Lindsay Award in 2016-17.

He played his 1,000th career game in 2018-19 and remained effective in 2020-21, his 17th season, with seven goals and 29 points in 56 games.

As for the Wild's return, Devin Setoguchi played just two seasons and scored 32 goals in Minnesota  before a trade to Winnipeg, and Charlie Coyle was there seven years and topped out at 21 goals in 2015-16 before a trade to Boston in 2019.

And here's one that worked out well for both sides.

A mid-summer trade between the Pittsburgh Penguins and Toronto Maple Leafs in 2015 involved six players, three picks and left both teams better than they were before it occurred.

The Penguins already had a roster boasting the likes of Sidney Crosby and Evgeni Malkin but were six seasons removed from their most recent championship, including three first-round playoff exits. The Maple Leafs, meanwhile, had missed the playoffs in nine of the previous 10 seasons and hadn't won a series since 2004.

By sending Phil Kessel, Tim Erixon, Tyler Biggs and a pick to Pittsburgh, Toronto netted Kasperi Kapanen, Scott Harrington, Nick Spaling and a pair of picks. The Maple Leafs experienced one more season on the outside looking in, but it got them the No. 1 overall draft slot that subsequently turned into Auston Matthews.

The Penguins, on the other hand, got 49 regular-season goals and 18 more in the playoffs over the next two seasons from Kessel, who was a key piece in securing two more Stanley Cups.

He spent two more seasons with Pittsburgh before a trade to Arizona in 2019.

Kapanen blossomed into a middle-six player over parts of five seasons with Toronto, and the pick with which he arrived was ultimately turned into starting goaltender Frederik Andersen.

Win. Win.

Remember that Oilers fan advice from a few slides back?

Try it again here.

The deal that sent former No. 1 pick Taylor Hall from Edmonton to the New Jersey Devils in 2016 is still considered among the most dubious moves made by a franchise that traded a prime Wayne Gretzky.

The Devils got Hall in a one-for-one exchange for defenseman Adam Larsson, who was selected fourth overall a year after Hall's draft in 2011.

Initial reaction suggested Oilers GM Peter Chiarelli had been fleeced, but the scales leveled somewhat when Edmonton reached the playoffs in 2017 thanks to Larsson's steady presence on the blue line. It shifted back toward New Jersey's direction in 2018, though, when Hall broke through for a Most Valuable Player award.

Hall has been something of a journeyman since that breakout, spending parts of two more seasons with the Devils before a trade to Arizona, a free-agency signing in Buffalo and another trade to Boston.

Larsson, meanwhile, stayed with the Oilers through the end of 2020-21 and reached the postseason twice more before he was exposed to the Seattle Kraken in the expansion draft and signed a deal with the NHL's newest team that will cover four years.

Had Hall stayed with a burgeoning Connor McDavid, who knows? But given Larsson's stability, this one seems a lot better on both ends now than it did back then.

Call this one the first of a two-part exchange.

An early summer day in 2011 saw the Philadelphia Flyers attempt to reshape their franchise by dealing away two young, emerging stars in exchange for even younger prospects from two teams.

In Part 1, they sent 26-year-old center Jeff Carter to the Columbus Blue Jackets for three-year winger Jakub Voracek and first- and third-round picks in the draft scheduled just a few days later.

Carter had been picked 11th overall in 2003 and scored 181 goals in six seasons with the Flyers. He also made an appearance in the All-Star Game in 2011. But he had been the source of concern about off-ice issues and was on the verge of controlling his fate with the activation of a no-trade clause.

Instead, he headed to the Blue Jackets for a stay that lasted just 39 games before he was dealt to the Los Angeles Kings in 2012. He stayed in L.A. and won two titles through 2021, when he headed to Pittsburgh in a trade deadline deal.

As for the Flyers, Voracek was a stalwart for 10 seasons and scored 177 goals before another trade this summer sent him back to Columbus. Philadelphia turned the first-round pick from the Carter deal into Sean Couturier, who's scored 174 goals of his own in 10 seasons on Broad Street.

It also freed up the salary space that helped them get Bryzgalov.

But still. Not too bad.

And here we are at Part 2.

On the same day the Flyers exiled Carter to Columbus, they also sent his good friend and fellow standout Mike Richards to the Los Angeles Kings for Wayne Simmonds, Brayden Schenn and a 2012 draft pick.

Richards had scored at least 23 goals for four straight seasons and was three years into a 12-year contract worth $69 million.

Nevertheless, he was off to the West Coast, where he produced 44 points in his initial season and added 15 more in 20 playoff games as the Kings worked their way to a Stanley Cup.

He added another title to the resume two years later, but his stint in Los Angeles ended the following season when he was first waived and later had his contracted terminated by the Kings. He played just one more season in the NHL, appearing in 39 games with the Washington Capitals, before retiring.

Similar to the Carter deal, the Flyers made out well in the long run. Simmonds played in Philadelphia for parts of eight seasons and Schenn was there for six, and the pair combined for nine seasons of 20-plus goals.

Hard to believe there was a day the Hall-Larsson deal didn't dominate hockey news.

Sharing billing on June 29, 2016, was a trade between the Montreal Canadiens and Nashville Predators that resulted in stalwart defensemen P.K. Subban and Shea Weber changing locker rooms and jerseys.

Heading from Canada to Tennessee was Subban, who had won the Norris Trophy in 2013 and had eclipsed 40 assists for three consecutive seasons. Moving north was Weber, who had been with the Predators for parts of 11 seasons and was even more prolific offensively, scoring 20 or more goals three times.

Subban was two seasons into an eight-year, $72 million contract that lasts through the upcoming NHL season and was on the verge of enacting a no-trade clause that would severely hamper the Canadiens' ability to move him. Weber's deal was even more onerous, covering 10 more seasons at $7.86 million apiece.

The Predators seemed a clear winner early on as they reached the Stanley Cup Final in 2017 and Subban was again a Norris finalist a season later, but it soured after the third year, and he was dumped to the New Jersey Devils on Day 2 of the 2019 NHL draft.

Weber, meanwhile, became the Canadiens captain and played 22 games in their unlikely run to last season's Cup final, where they lost to Tampa Bay.

Myriad injuries have mounted and will keep him off the ice for the 2021-22 campaign, making retirement a possibility in spite of the five years remaining on his contract.