Bruins All-Time Best and Worst Trade Deadlines

The 2022 NHL Trade Deadline is less than one month away and as usual, there should be a plethora of transactions that take place prior to the deadline passing. The Boston Bruins have been one of the more active teams at the deadlines in recent years and have had varying degrees of success when making moves to try and bolster their team either in the short-term or with long-term implications in mind.

Don Sweeney Bruins
Don Sweeney, Boston Bruins, has been one of the more active general managers in the NHL at the Trade Deadline over his tenure with the team. June 22, 2018 (Amy Irvin / The Hockey Writers)

With a history as long as the Bruins’ there are bound to be good trades and bad trades that can be identified over the years. With that in mind, let’s take a look at the five best and the five worst Trade Deadline deals made by the Bruins in their franchise’s history. This list will include the five best and five worst, but will not be listed in any specific order within their own respective category.

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Following that, let’s also take a look at the last five Trade Deadlines and see what moves were made by Don Sweeney in his first five years as general manager of the Bruins. Again, though there will be five trades listed here, they will not be ordered in any specific ranking.

Bruins’ 5 Best Trade Deadline Moves

Bruins Acquire Mark Recchi From Lightning

When the Boston Bruins acquired Mark Recchi and a 2010 second-round pick from the Tampa Bay Lightning in exchange for Martins Karsums and Matt Lashoff in 2009, they picked up a crucial cog to what would eventually become a Stanley Cup-winning team. Recchi, the veteran forward who was already a sure-fire Hall of Fame player, would play in 180 regular-season games with the Bruins and would score 42 goals and 107 points. He’d also play in 49 playoff games with the Bruins, scoring 14 goals and 30 points, including five goals and 14 points in the 2011 Stanley Cup Final run.

On the flip side, the Lightning would be getting two players who would combine for just 46 games in the NHL.

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There isn’t a whole lot to say for the Lightning as far as this deal is concerned other than the fact that they were very clearly the losers of this deal by just about any sort of evaluation tactic imaginable. The second-round pick acquired by the Bruins in this deal would also be important, but more on that one later. Even without this pick involved in the deal, the Bruins would make this trade again 100 times out of 100.

Bruins Trade Craig Janney and Stephane Quintal for Adam Oates

One of the best trades made by the Bruins in the history of their franchise and not just in the wake of the Trade Deadline came in 1992. The Bruins would ship off forward Craig Janney and defender Stephane Quintal to the St. Louis Blues in exchange for Adam Oates. Admittedly, this wasn’t necessarily a “Trade Deadline” move, but it did happen close enough to the Deadline itself (about a month prior) that it counts for the same purpose.

It shouldn’t be hard to figure out why this deal was such a good one for the Bruins.

Unfortunately, Janney was forced to retire early from the NHL due to blood clots at just 31 years old, but he did still play in 760 games in his career, including another 498 games following the deal. Though Janney and Quintal would both go on to have good careers in the NHL even after their time in Boston, the Bruins came away with the best player in this deal.

Oates would immediately make an impact in Boston, scoring 10 goals and 30 points in 26 games to close out the 1991-92 season. He’d top that off with another five goals and 19 points in 15 postseason games.

Adam Oates
MONTREAL 1990’s: Adam Oates #12 of the Boston Bruins skates against the Montreal Canadiens in the early 1990’s at the Montreal Forum in Montreal, Quebec, Canada. (Photo by Denis Brodeur/NHLI via Getty Images)

In his first full season with the Bruins, Oates would put together a career year. Playing in 84 games, he’d score a career-high 45 goals, 97 assists and 142 points; all would remain his career-high marks through the end of his career. He proved to be an exceptional talent and is widely regarded as one of the best passers in the history of the game.

In 368 games with the Bruins, Oates would score 142 goals and 499 points and certainly left an impact in Boston in his half-decade with the team. His tenure with the team ended on a sour note as the veteran center was disgruntled with the Bruins due to the lack of talent put around him. The Bruins would accommodate trade demands and would ultimately get younger in the subsequent deal that sent him out of Boston.

Oates may have had his fair share of issues with management in Boston at the time, but that shouldn’t take away from how exceptional of a player he was for the team for the time he was there.

Bruins Acquire Dennis Seidenberg and Matt Bartkowski

Remember that second-round pick that was acquired along with Recchi from the Lightning? Well, it would go down as more than just a throw-in, as fate should have it. The Bruins would package Byron Bitz, Craig Weller and that second-round pick to the Florida Panthers in 2010 in exchange for defender Dennis Seidenberg and the rights to defender Matt Bartkowski.

While Bartkowski would end up playing in parts of five seasons with the Bruins, totaling 131 regular season and 15 playoff games, the acquisition of Seidenberg was the big news in this deal. The veteran defender would play in 401 regular games with the Bruins during his tenure in Boston. He’d also add another 50 playoff games in three seasons during that tenure with two such runs resulting in a Stanley Cup Final berth.

At the time, Seidenberg and Zdeno Chara would be considered one of the most fearsome shutdown defensive pairings in the entire NHL. It was a match made in heaven and in the end, all it cost the Bruins was Bitz (who would play in 17 more games in the NHL and only seven of which came in Florida), Weller (who would never get another NHL opportunity) and a second-round pick which was used on defender Alex Petrovic. Weirdly enough, Petrovic would end up playing with the Bruins years later.

Bruins Acquire Taylor Hall From Sabres

When the Bruins traded for Taylor Hall at the 2021 NHL Trade Deadline, they immediately appeared to be big-time winners of the deadline. They’d also acquire Curtis Lazar in this deal to help solidify their bottom-six while getting David Krejci a bonafide star winger to play alongside in Hall.

Hall quickly looked like a superstar in Boston and had returned to for after an incredibly disappointing tenure with the Buffalo Sabres. His contributions would turn into a long-term extension with the Bruins which ultimately solidified him as their second-line left winger for the foreseeable future.

Taylor Hall, Boston Bruins
Taylor Hall has been a steal for the Boston Bruins since being acquired from the Buffalo Sabres in 2021. (Amy Irvin / The Hockey Writers)

The value to acquire such an important core piece to the team was the real kicker, though, as it would cost the Bruins a second-round pick and Anders Bjork to get this deal done. At the end of the day, that’s high-way robbery for the player Hall has been throughout his career.

Krejci may not be a Bruin anymore, but Hall and David Pastrnak have united to become a lethal duo on the Bruins’ second line this season.

Bruins Trade Sergei Samsonov for Draft Pick That Became Milan Lucic

In recent years, the Bruins have been exclusively buyers at the Trade Deadline. This shouldn’t be surprising considering the fact that the team has remained competitive and at least in the hunt for a playoff spot for the last 15 seasons. One such season that saw them in the role as “seller” rather than “buyer” though, was the 2005-06 season.

The Bruins would trade Sergei Samsonov to the Edmonton Oilers in exchange for Marty Reasoner, Yan Stastny and a 2006 second-round pick.

Samsonov was a fan-favorite in Boston and would score 164 goals and 376 points in 514 regular-season games in his seven-plus seasons with the Bruins. Though he was still playing well in his final season with the team, the Bruins were a team that didn’t appear to be trending in the right direction by any stretch of the imagination at the time of the March 9, 2006 trade. With an expiring contract to consider, the Bruins did what they could to recoup some value for what was one of their best players at the time.

Samsonov would go on to play in another 374 NHL games following this deal, though he’d only play in 19 total games with the Oilers before signing with the Montreal Canadiens in the offseason.

In return for Samsonov, the Bruins would get 38 games of Stastny, 19 games of Reasoner, and a second-round pick. That pick, of course, would be used to select Milan Lucic 50th overall from the Vancouver Giants.

Milan Lucic Calgary Flames
Milan Lucic, once a fan-favorite in Boston, now plays with the Calgary Flames (Amy Irvin / The Hockey Writers)

Lucic would end up giving the Bruins eight seasons, including two Stanley Cup runs. He was a focal point of the team’s successful run in 2011 and would play traditional Bruins’ hockey through his 566 games in Boston. He’d score 139 goals and 340 points in the regular season in Boston while also adding 26 goals and 61 points in 96 playoff games.

Though there have been some big hits in the history of the Bruins when it comes to Trade Deadline moves, there have also been some big misses as well.

Bruins’ 5 Worst Trade Deadline Moves

Bruins Trade Joe Juneau for Al Iafrate

One of the most puzzling moves in the history of the Bruins’ franchise came on March 21, 1994. The Bruins would acquire Iafrate – who, to his credit, was an exceptional talent who played exactly the style of hockey that the Bruins were known for. He was able to produce offensively from the blueline, he boated the NHL’s hardest shot for years and had score 10 goals and 45 points in 67 games with the Capitals prior to this trade.

Unfortunately, Iafrate would only suit up in 12 regular-season games for the Bruins and 13 playoff games, totaling eight goals and 17 points (five goals and 13 points of which came during the regular season). Knee injuries would derail Iafrate’s career and he would play in just 65 more regular season and playoff games after that with a fairly lengthy absence in between his tenure in Boston and his tenure with the San Jose Sharks.

If Iafrate would have had better luck with injuries, perhaps this deal would be looked upon differently at the end of the day. Unfortunately, that isn’t the reality we live in.

The cost of acquiring a rental in Ifarate was Juneau who was coming off one of the best rookie seasons in the history of not just the Bruins, but the NHL. He would score five goals and 19 points in 14 games during the 1991-92 season which immediately created a buzz around what he could do in a full rookie season the following year. Juneau wouldn’t disappoint either as he’d score 32 goals and 102 points as a rookie. It wasn’t like he was a one-hit-wonder, either, as he had scored 14 goals and 72 points prior to his trade to the Capitals for Iafrate.

Related: 7 Cool Things About Zdeno Chara

Juneau would go on to play in 828 NHL games, scoring 156 goals and 572 points and could have certainly been a star player in Boston for years had the team not given up on him so soon.

Bruins Trade For Brett Connolly

When the Bruins traded Johnny Boychuk to the New York Islanders in exchange for two second-round picks in 2014, they did so strictly due to cap restrictions. It was a deal that hurt fans, noticeably made the Bruins worse defensively and to make matters worse, didn’t garner the return that anyone would have hoped for given the talent Boychuk possessed.

Fast-forward to the 2015 Trade Deadline and the Bruins would trade two second-round picks to the Tampa Bay Lightning in exchange for forward Brett Connolly. The Lightning had drafted Connolly sixth-overall in 2010 and the right-shot, right-winger had struggled to live up to expectations while in Tampa.

Filling a position of need for the Bruins, Connolly never amounted to much in Boston either despite getting opportunities to play alongside Patrice Bergeron and Brad Marchand on the top line. Before he could ever even get into action, Connolly would suffer a broken finger in practice and would be sidelined for the next month as a result. He’d play in just five regular-season games that season with the Bruins, failing to find the back of the net and recording two assists. He’d play in 71 games with the Bruins the following season and would score nine goals and 25 points.

Connolly would leave for the Capitals in the offseason and would go on to score 15, 15, 22 and 19 goals in the next four seasons, the last of those seasons coming with the Florida Panthers. Not only did the Bruins fail to recoup adequate value for Boychuk, they also gave up on Connolly too soon as he proved to be a serviceable middle-six player at the very least.

Bruins 2016 Trade Deadline

This may not be an individual trade or action, but the 2016 Trade Deadline as a whole was an undeniable flop for the Bruins. Missing the playoffs for the first time since 2007 the previous season, the Bruins were looking to return to playoff contention after just a one-year absence.

When the Trade Deadline rolled around, the Bruins considered themselves buyers and would retain the services of pending unrestricted free agent Loui Eriksson rather than recouping value for him from another team. Beyond that, the Bruins would also trade a 2016 fourth-round pick and a 2017 second-round pick to the New Jersey Devils for forward Lee Stempniak, as well a 2016 third-round pick and fifth-round pick and Anthony Camara to the Carolina Hurricanes for John-Michael Liles.

The Bruins underwhelming additions and the retention of Eriksson would prove fruitless as the team would miss the playoffs for the second-consecutive season. Eriksson would also leave town and sign a six-year contract with the Vancouver Canucks in the offseason. Stempniak played in just 19 games for the Bruins, scoring three goals and 10 assists before returning for another two-game stint with the team three seasons later. The Bruins would get 53 regular season and six playoff games from Liles over the next two seasons.

Bruins Trade Bourque and Andreychuk to Avalanche

This trade is a weird one given the circumstances that surrounded it. Ray Bourque, one of the greatest defenders and players to ever play the game of hockey, was as loyal as it got when it came to playing for the Bruins. Unfortunately, though, his loyalty hadn’t paid off in the form of a Stanley Cup win during his time in Boston.

Raymond Bourque Boston Bruins
Raymond Bourque was one of the most loyal players to the Boston Bruins during his career. (Photo by Denis Brodeur/NHLI via Getty Images)

At 39 years old, Bourque’s chances of winning a Stanley Cup at all were quickly dwindling given the fact that the Bruins were not a contender that season and didn’t seem primed to be one in the immediate future. So, as a parting gift for his loyalty, the Bruins would send Bourque to the Colorado Avalanche along with Dave Andreychuk in exchange for Martin Grenier, Samuel Pahlsson, Brian Rolston and a 2000 or 2001 first-round pick (the Bruins were able to choose and opted for the 2000 pick which became Martin Samuelsson at No. 27 overall.

Though the intentions for giving Bourque a chance at winning were noble, it was still a very lackluster return given what he should have been able to fetch. This is especially true when there were a few other teams in the NHL, like the Detroit Red Wings and Dallas Stars who likely could have bid up the price.

In the end, people will remember this trade as one that was done to help Bourque and it may not be fair to call it a bad deal in that regard. Still, it feels weird that the team couldn’t get more than they did; this is especially true when considering Samuelsson (14 games, one assist), Pahlsson (17 games, two points) and Grenier (zero games) were such irrelevant contributors for the Bruins.

Bruins Trade David Backes, Axel Andersson and 2020 1st-Round Pick for Ondrej Kase

When the Bruins traded for Ondrej Kase at the 2020 NHL Trade Deadline, they were also able to get out from under 75% of David Backes’ contract through the remainder of that season and the following one. The cost was high, but it also made sense at the time given what the underlying numbers said about Kase and the added benefit of getting rid of most of the remaining money on Backes’ deal.

Unfortunately, the Bruins would get just nine total regular-season games out of Kase and 11 total playoff games over the two seasons they had his services due to ongoing injury issues.

Ondrej Kase Boston Bruins
Ondrej Kase played in just nine regular-season and 11 postseason games with the Boston Bruins. (Amy Irvin / The Hockey Writers)

Though this trade may not have been that bad of a deal at the time, moving on from a first-round pick, the team’s highest-drafted player from just one season prior and also having to retain salary in this deal in exchange for so few games just can’t be seen as anything but a disaster of a deal. The same way a deal can turn into a good one down the line depending on how things turn out, this deal turned into an awful one just given the circumstances.

Bruins Last 5 Trade Deadlines

2017

In 2017, the Bruins would trade a 2018 conditional 6th round pick (Jets) became a fifth-round pick because the Bruins made the playoffs in 2017 and Stafford played in half of the Bruins’ remaining games in the 2016-17 season in exchange for Drew Stafford. Stafford would play in 18 regular season and six postseason games with the Bruins.

2018

In 2018, the Bruins would trade a 2019 conditional fifth-round pick (became a fourth-round pick because the Bruins advanced to the second round of the playoffs) for Tommy Wingels. The pick would have also converted if Wingels re-signed with the Bruins – he hasn’t played a game in the NHL since the 2018 playoffs.

The Bruins would also trade Ryan Spooner, Matt Beleskey (with 50% of his salary retained), Ryan Lindgren, a 2018 1first-round pick and a 2019 seventh-round pick in exchange for Rick Nash (who has 50% of his salary retained by the New York Rangers). This deal helped free up money from Beleskey’s contract, but it ultimately turned into a disaster deal given the fact that Nash retired after that postseason. He played in just 11 regular season and 12 postseason games in Boston.

The Bruins would also trade Rob O’Gara and a 2018 third-round pick for Nick Holden that season in a move that helped bolster their blueline. Ultimately, this would serve as a good decision given how big injury concerns were for the Bruins that season.

The Bruins also recouped a 2018 third-round pick from the Florida Panthers in exchange for Frank Vatrano that year. Though Vatrano would go on to succeed with the Panthers, his value was quickly dwindling in Boston and a change of scenery was needed for both parties.

2019

The 2019 Trade Deadline was a good one for the Bruins. They’d trade a 2019 second-round pick and a 2020 fourth-round pick to the New Jersey Devils in exchange for Marcus Johansson. Though Johansson would only spend 10 regular season and 22 playoff games with the Bruins, his contributions were enough to help the Bruins come within one game of winning the Stanley Cup in 2019.

Expecations were high for Ryan Donato in Boston but the Bruins would cut bait sooner than expected when they traded him and a fifth-round pick in 2019 to the Minnesota Wild in 2019. This deal has worked out very well for the Bruins as Coyle remains an integral piece on the Bruins team down the middle.

2020

As mentioned, the Bruins would trade a big package for Kase at the 2020 Trade Deadline in another bad move in hindsight. An alternative move they made was trading Danton Heinen to the Anaheim Ducks in exchange for Nick Ritchie. In the end, that deal can be viewed as a wash for both sides.

2021

The Bruins could be considered fairly significant winners of the 2021 NHL Trade Deadline considering they were able to acquire Hall and Lazar in exchange for Bjork and a 2021 second-round pick. This deal has proven to be even better for the Bruins considering both players have served as more than just rentals for the team with Hall signing an extension in the offseason and Lazar playing a key role on the fourth line for the team.

The Bruins would also acquire Mike Reilly from the Ottawa Senators in exchange for a third-round pick in 2022. this deal also worked out well for the Bruins in the early goings as he was an effective puck-moving defender for the team. Since signing a new deal in the offseason, though, Reilly hasn’t been quite as effective for the Bruins. Still, a three-year, $9 million contract isn’t the worst contract in the league by any stretch.

The Bruins are once again buyers heading into the 2022 NHL Trade Deadline and should be active with so many major areas of need that have to be filled.