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Peter Chiarelli’s 10 Worst Moves as an NHL General Manager

Stop me if you’ve heard this before, the Oilers are bad. A team with Connor McDavid, Leon Driasital, and Ryan Nugent-Hopkins should not be this bad. Bruins fans are well accustomed to watching Peter Chiarelli taking great young teams and turning them into major disappointments.

Now that he’s ruining teams on the other side of the continent, lets rank Peter Chiarelli’s 10 worst moves as an NHL General Manager, starting with two honorable mentions because 10 is not enough (lol), Down Goes Brown style.

Honorable Mentions:

HM 1: The 2011 Trade Deadline

The Move: Trading Blake Wheeler, Mark Stuart, Joe Colborne, a 1st round pick and two 2nd round picks for Tomas Kaberle, Rich Peverley, and Chris Kelly in three seperate deals at the 2011 deadline.

Why it made sense: This was the year. They were going all in. Kaberle seemed like a no-brainer, and the move that would put them move the top.

Why it didn’t: Thats a hiiigh price for Kaberle. Is Peverley really better than Wheeler? and is it too soon to give up on Wheeler? Do they really need Chris Kelly and is he really worth a second?

The Result: In hindsight, the Peverley and Kaberle trades were bad, but it doesn’t matter. They won the cup. That’s why they aren’t in the top 10. Winning a cup erases everything, which is why only one of the the top 10 is prior to 2011.

HM 2: Trading a 5th Round Pick for Adam McQuaid

The Move: Acquiring junior defenseman Adam McQuaid for a 5th round pick from Columbus. That 5th round pick just happened to turn into Jamie Benn.

Why it made sense: Ok this one’s joke

Why it didn’t: Uhhhh

The Result: Years of mockery that the Bruins traded Adam McQuaid for Jamie Benn even though they didn’t

Let’s get into the top 10, for real this time.

10. Signing Jarome Iginla

Why it made sense: After Nathan Horton left for Columbus, Iginla was the perfect replacement. After he rejected a trade to the Bruins in March and decided to go to the Penguins because he wanted a chance to win the cup and later get swept by the Bruins in the Eastern Conference final, the Bruins gave him a second chance to come to Boston, where he now calls his home in his retired life.

Why it didn’t: They had no cap space. They used their remaining 1.8 million on his cap hit and the rest of the 4.8 million in bonus money, which would

The Result: basically screw the Bruins over for the next three years. Iginla’s bonuses put the Bruins 5 million dollars over the cap, giving the Bruins 5 million dollars in overages next season, forcing the Bruins to trade Johnny Boychuk, and leave a gaping hole on David Krejci’s right wing, which to this day has not been filled. Among other things, Iginla’s overages led to the demise of that Bruins golden age.

9. Trading Johnny Boychuk to the Islanders

The Move: Days before the beginning of the regular season, the Bruins traded fan favorite Johnny Boychuk to the Islanders for two 2nd round picks, which turned into Brandon Carlo and Ryan Lindgren.

Why it made sense: It had to be done. In hindsight they probably should have traded Dennis Seidenberg, but that didn’t make sense at the time. Boychuk had one year left and was due for a big raise in free agency, and trading Boychuk’s 3.67M salary allowed the Bruins to put Marc Savard on LTIR after just signing RFAs Riley Smith and Torey Krug

Why it didn’t: Peter Chiarelli botched the Bruins cap situation so badly that he was forced to make this move. Boychuk was part of the 2011 core, and it was not only tough to see him go, but it made the Bruins immediately worse.

The Result: His departure forced rookies Torey Krug and Kevan Miller to play big minutes. Here’s a fun little tid-bit: Adam McQuaid led the Bruins in ice time on opening night in 2014 with 21:47 TOI. Neato. The Bruins missed the playoffs after winning the presidents trophy, without Boychuk, Iginla and Tyl-

8. Signing Kris Russell to a 4 year 4 Million dollar contract

The Move: This past offseason, Peter Chiarelli, for some god forsaken reason, signed Kris Russell to a 4 year, 4 million dollar contract extension. Why on earth…

Why it made sense: He blocks shots apparently…

Why it didn’t: There is this big debate about Kris Russell between the analytics community and the “old school watch the game” people. Well apparently because he tries hard and blocks shots he is a top four defenseman. Ignore the analytics numbers, if you lead the league in blocked shots that probably means you don’t have the puck very much, which is bad. Not only that, but Kris Russell’s ice time is that of a bottom pairing, maybe fourth, defenseman, averaging 18:45 TOI/GP this season.

The Result: Still to be seen, but as of now, they’re playing a bottom pairing defenseman 4 million dollars. Not great.

7. Trading Kris Versteeg for Brandon Bochenski

The Move: In early 2007, the Bruins acquired AHL superstar and promising prospect Brandon Bochenski in exchange for thier own promising AHL star Kris Versteeg… something about the name Kris.

Why it made sense: Bochenski was lighting it up in the AHL for Chicago and wasn’t getting a chance with the big club. He scored 33 goals and 66 points in 35 AHL games before being traded to the Bruins. Not a bad gamble for a rebuilding team that could use scoring.

Why it didn’t: That’s what it was, a gamble. Versteeg was having AHL success of his own, scoring 49 points in 43 AHL games for Providence, and was just 20 years old, four years younger than the 24 year old Bochenski.

The Result: Versteeg has gone on to play 11 season in the NHL and counting, winning two cups with Chicago and being a locker room favorite, while Bochenski… hasn’t. He scored 11 goals and 28 points in 51 games for the Bruins before bouncing around in the AHL and NHL and ultimately ending up in the KHL. Ultimately a gamble that didn’t work out, but what if the Bruins had never trade Versteeg…?

6. Extending Dennis Seidenberg 

The Move: Just two games into the 2013/14 season, the Bruins extended Seidenberg for four years, worth 4 million per year.

Why it made sense: Outside of Zdeno Chara, Seidenberg was the heart and sole of the Bruins defense. They don’t win the cup without him in 2011 and may not make their 2013 run without him either. It would have been really tough to let him walk

Why it didn’t: Because you don’t sign 32 year olds with the mileage he had to four year contracts.

The Result: A buyout two years later. Seidenberg blew out his knee 34 games into his season, and was never the same. He was bad in 2016, leading to new GM Don Sweeney cutting ties, which probably wasn’t a good move in it’s own but besides the point. Nobody could have predicted the significance of the drop off Seidenberg had, but signing a 32 year old who had played 10 years in the NHL with the style he played was a horrible idea, and he will continue to count against the Bruins cap through 2020.

5. Trading Jordan Eberle for Ryan Strome

The Move: This past summer, Chiarelli traded Jordan Eberle to the Islanders straight up for Ryan Strome.

Why it made sense: Eberle had regressed down to a career low .62 points per game and it appeared it might be time for a change. That’s not how Peter Chiarelli explained it, however. He said it was because the Oilers needed cap flexibility. The Oilers currently have almost 9 million in cap space.

Why it didn’t: They were trading a bonafide top six scorer for a guy who’s production had dropped to just 28 and 30 points since his 50 point rookie season. Strome was a 5th overall pick, and maybe he was another guy who maybe needed a change of scenery, but straight up for Eberle?

The Result: Eberle has thrived with the Islanders and their high flying offense, scoring 14 goals and 34 points in 44 games. Meanwhile, the Oilers accepted the trade didn’t work out about a month into the season, and have been unhappy with Strome with just 17 points in 46 games, which by the way is on pace for the second best season of Ryan Strome’s career. Do we see the problem here?

4. Acquiring Griffen Reinhart for Barzal pick

The Move: At the 2015 draft, Chiarelli’s first draft with Edmonton, the Oilers traded a 1st round pick, 17th overall, and their 2nd round pick the next day in exchange for Griffen Reinhart

Why it made sense: The Oilers were desperate for defensemen. A young 21 year old defenseman who had been picked 4th overall just 3 years ago seemed like somebody who could fit the mold of what the Oilers were looking for.

Why it didn’t: Reinhart struggled to crack to Islanders lineup the year prior, playing in just 8 games, and wasn’t particularly great in AHL Bridgeport either. It was a 50/50 gamble at best, especially with the quality of picks they were giving up.

The Result: Reinhart played 29 games in 2015/16, recording just one assist. He played the entire 16/17 season in the AHL with the exception of one playoff game, and he was claimed by the Golden Knights in the expansion draft in June, who later placed him on waivers and assigned him to the AHL. Meanwhile, the picks they traded turned into Mathew Barzal, who could win the Calder this year, and Mitchell Stephens, who is currently in the AHL and stared for Canada in the World Juniors last year.

3. Trading Taylor Hall for Adam Larsson

The Move: The trade is one for one

Why it made sense: Uh, the Oilers needed defense and Adam Larsson is a defenseman?

Why it didn’t: Because Taylor Hall is an elite forward who can score a lot of goals and a lot of assists and make your offense better in so many ways and that’s literally what the Oilers need right now to play with McDavid and those aren’t easy to find and you traded one straight up for a 4th maybe 3rd defenseman at best you idiot.

The Result: The Devils are pretty good and the Oilers are not.

2. Trading Tyler Seguin

The Move: On July 4th, 2013, the Bruins traded Tyler Seguin, Rich Peverley, and Ryan Button to Dallas for Loui Eriksson, Reilly Smith, Matt Fraser, and Joe Morrow.

Why it made sense: I defended this trade for a long time, but there is no defending it now. I genuinely believe that this wasn’t a bad trade at the time it happened. Seguin was a superstar in the making, but he was replaceable on the Bruins roster. Bergeron and Krejci weren’t going anywhere, and (believe it or not) they actually got a haul back. Loui Eriksson had scored 70 points in each of the last three full seasons, and was the most underrated superstar in the league. Joe Morrow was a first round pick who the Stars had just traded their captain (Brenden Morrow) and a second to acquire. Matt Fraser’s shot and physicality were both signs that pointed to his AHL success turning into middle-six NHL production, and Reilly Smith, the seemingly least valuable piece that the time, has turned into a legitimate top six winger in the NHL. The return was significant, even for a guy like Seguin.

Why it didn’t: You’re trading a 20 year old #2 overall pick who had just scored 29 goals and 67 points a year prior in 2012, and getting better. You can argue no return short of an Eric Lindros return is worth a guy like him.

The Result: Just 4 years later, the Bruins have nothing to show for Seguin. Eriksson left for Vancouver after 3 seasons, Fraser was lost to waivers, Morrow was non-tendered, and Smith was traded for Jimmy Hayes, who was bought out. Think of the worst case scenario, that’s it. Disastrous.

 1. Throwing Away a Dynasty

The Move: Turning a should-be dynasty into a non playoff team in two years.

Why it made sense: It didn’t

Why it didn’t: Someway, somehow, Peter Chiarelli turned a team that was a minute away from forcing a Game 7 of the Stanley Cup Final (I cry everytime) with a core of Dougie Hamilton (19), Tyler Seguin (20), Ryan Spooner (20), Torey Krug (21), Brad Marchand (24), Milan Lucic (24), Tuukka Rask (25), David Krejci (26), Patrice Bergeron (27), and Nathan Horton (27) into a non playoff team in two years. This team was set up for the next decade, and he just threw it away. He put new GM Don Sweeney, who made his own mistakes, in such a horrible position that he had no choice but to go through a semi rebuild.

The Result: 3 years of continuous frustration. It was tough, but last February it all took a turn. Now, the old core that Chiarelli didn’t give away of Bergeron, Marchand, Krejci, Rask, and Krug is leading a new charge of contenders. They’ve seemed to find the perfect mix of youth and veterans, with the likes of Charlie McAvoy, Danton Heinen, Jake DeBrusk, and Matt Grzelcyk becoming real contributors to a team that’s once again contending for a Stanley Cup. That 2013 team should have been set up for 5-7 of contending, but instead, just 5 years later, there is a completely new core of young players coming in, and Sweeney seems to have done a pretty good job of cleaning up Chiarelli’s mess.


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  1. Pingback: Every GM's Best and Worst Trade: Pacific Division - The Intersection

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