The Time-Traveling GM

By Chris Gere

An Alternate Timeline of the 2011–2020 Boston Bruins

Let’s set the stage: it’s the 2011 offseason. Peter Chiarelli is sitting in his office smoking cigars, counting money, and laughing about nothing in particular (I assume this is what rich people do when they’ve achieved their wildest dreams). Suddenly, a phonebooth appears before him in a flash of light. A person opens the phonebooth door and steps into the office. He’s young and handsome and has an impressive quarantine mustache. He pulls up #HockeyTwitter on his phone and shows Chiarelli what is to become of him. Adam Larsson, Milan Lucic, failing to make the playoffs with the best player in hockey, all of it. On the spot, he decides to step down from his post, and he names this mysterious time traveller as his successor.

(It’s me, I’m the new GM of the Boston Bruins).

With the benefit of hindsight, it is my job to steer the Bruins in the proper direction, and ensure that they win the Stanley Cup in the year 2020. (In this scenario, I’ve also used my platform to start a global campaign not to eat bats, so the 2019–20 season will have continued without a hitch).

Now that we understand this realistic scenario, let’s set some ground rules:

  1. I’m not going to add random free agents. This may be a fantasy, but I’d like to keep at least a guise of realism. We can’t be out signing guys like Steven Stamkos to lowball contracts and thinking that’s cool.
  2. I will be re-litigating the drafts, but only the first round of each draft. Only players taken within ten picks of the Bruins’ pick will be eligible.
  3. In this exercise, we will assume that nothing I do as GM along the way can affect the Bruins’ place in the standings, so I can’t just gut the team and tank for McDavid, because that’s stupid. In that vein, I’ll try not to do anything that would make the team way worse along the line.
  4. Should go without saying, but we have to stay under the cap because that’s how the NHL works.
  5. Any contract that a former Bruin signed with another team is assumed to be the same contract that they would have accepted with the Bruins. It’s not perfect, but, in this scenario, I’ve seen the future, and I know that these players will sign for this money and term.
  6. Finally, I’m not going to cover every minor trade and signing. This would get really boring if I spent time talking about why the Bruins should or should not have traded a fourth-round pick for Joe Corvo. If your favorite player isn’t mentioned and isn’t on the final roster, assume he’s in the AHL. Also, get a new favorite player.

Let’s get after it.

The 2011–12 Season

First up is the 2011 NHL Entry Draft. Even with the benefit of hindsight, there was no better pick than Dougie Hamilton. At this point, I don’t know for sure if we’re going to keep him for the 2020 season, but I want it to be an option because he’s an outstanding player. Next, we don’t have to make too many moves because not a lot that happened in the 2011–12 season directly affects the 2020 roster. On the other hand, we can trim some fat along the way to ensure that we don’t go over the cap at any point on our way to 2019–20. For example, I’m not going to re-sign Rich Peverley to that three-year, $9.75 million extension.

Patrice Bergeron initiates a long-distance hug with David Krejci

David Krejci signs an extension for three years, $15.75 million, and Johnny Boychuk re-signs for three years, $10.1 million. This ensures the team is competitive enough to lose to Brayden Holtby in the first round of the playoffs. Also, in a very obvious move, we’re going to sign undrafted free-agent Torey Krug.

The 2012–13 Season

Alas, despite my best time-travelling efforts, I am unable to do anything to stop the lockout. Darn, it looks like the Blackhawks will have to keep that asterisk. My first “move” is not offering Chris Kelly a four-year, $12 million extension. He was a valuable player, but I have a fundamental aversion to overpaying bottom-six players unless they’re top-six players masquerading as bottom-six players (see: Charlie Coyle). Next, the whole Merlot Line re-signs for reasonable money.
With the 24th pick in the draft, we forego taking Malcolm Subban and go with Tanner Pearson. It May not end up mattering at all, but also it might, so we’re going for it. Right before the season, Brad Marchand signs a four-year, $18 million extension, Tyler Seguin agrees to six years, $34.5 million, and Milan Lucic re-ups for three years, $18 million.
For continuity, we’re going to keep all the midseason trades made this year. That means, when we discover that Tim Thomas is washed-up, we send him to the Islanders for a conditional second-rounder. It also means that we get the hilarious privilege of watching Jaromir Jagr play a really slow game of keep-away for a couple of months for the low, low price of a first-round pick.

The 2013–14 Season

This is where things start to get fun. Due to the Jagr trade, the Bruins don’t have a first-round pick, but don’t you worry, nobody in the late first; early second mattered at all in that draft. However, something interesting happens. I’m sitting on a lake, drinking a beer on July 4th, and new Dallas Stars GM Jim Nill calls me. I say, “Jim, first of all, how did you get this number? Second of all, don’t you know it’s a national holiday?” and I hang upon him. I wonder what he wanted. Oh well, I guess we’ll never know.
In need of a wing, we go out and sign legendary scorer Jarome Iginla for one season at $6 million. Tuukka Rask signs a free-agent deal for eight years, $56 million, and Patrice Bergeron locks in an extension for eight years $55 million.

Just to check in, the Bruins go into the season with the following roster:


Brad Marchand – Patrice Bergeron – Tyler Seguin

Milan Lucic – David Krejci – Jarome Iginla

Tanner Pearson – Carl Soderberg – Ryan Spooner

Danny Paille – Gregory Campbell – Shawn Thornton


Zdeno Chara – Dougie Hamilton

Dennis Seidenberg – Johnny Boychuk

Torey Krug – Adam McQuaid


Tuukka Rask

Chad Johnson

Yeah, okay, that all-lefty third line is kind of a disaster, and I’ll admit that the Seguin trade addressed some roster issues that led the Bruins to a President’s Trophy, but this team kicks ass. It’s definitely at least good enough to lose in the second round of the playoffs (sigh).

The 2014–15 Season

In real life, the Bruins extended Seidenberg before the 2013-14 season, effectively, if not intentionally, choosing him over Boychuk. I, knowing how quickly he ages out of the NHL, let him walk in free agency this offseason, which will save some valuable cap space down the road.


David Pastrnak celebrating being picked by the best GM in the league

Meanwhile, as sure as the third amendment prevents soldiers from quartering in your private residence during peacetime without your consent, we go ahead and select David Pastrnak with the 25th pick of the 2014 draft. I get out of my seat and laugh hysterically at all the GMs who passed on him. The other GMs don’t like me very much, but I don’t care.
As a huge Krejci fan, it pains me not to offer him a contract extension, but knowing that Seguin isn’t a career winger, I choose to let him play out the last season of his contract. Now, since I am a good GM, the Bruins don’t have cap issues that would necessitate a Boychuk trade. However, since I am a genius time traveller, I know that one of the picks we get for Boychuk turns into Brandon Carlo. Therefore, with seemingly no impetus, I trade Boychuk to the Islanders. Jeremy Jacobs fires me immediately. I ignore him and continue to act as GM. The rest of the front office recognizes my authority. Gary Bettman loses respect for Jacobs and quickly decides that he’s not Hall of Fame material.

The 2015–16 Season

Hold onto your shorts, because we’re going for a ride. In his first big splash as GM, Don Sweeney managed, through two deals, to turn a still-young-but-somehow-declining Milan Lucic into two first-round picks, Colin Miller, and Sean Kuraly. That’s just sorcery, so I’m going to keep those deals around. I am, however, undoing the Dougie Hamilton trade. It’s an understatement to say that Zack Senyshyn and Jakob Forsbacka Karlsson haven’t worked out thus far. Jeremy Lauzon seems like he might be serviceable, but that’s not the return you’re hoping for when you trade a young, top-pairing defenseman.
Even without the Hamilton trade, the Bruins have two first-round picks in the 2015 draft. Jake DeBrusk has been good, but there were better players available. Meanwhile, Jakub Zboril has been buried at the bottom of the Bruins defensive depth chart. With that in mind, we use our back-to-back picks to take Mat Barzal and Thomas Chabot. These guys are going to be super important from a financial perspective because the last year of their entry-level deals will be the 2019–20 season.
Now, this is where I shine. Matt Beleskey? I’m going to go ahead and let somebody else overpay for him. Zac Rinaldo? Dump your trash somewhere else, Philly. Jimmy Hayes? Sorry, Florida, we don’t have any Reilly Smiths to trade you. Whew. That felt good.

The 2016–17 Season

The 2016 draft was a coup for the Bruins. There are at least nine teams kicking themselves for letting Charlie McAvoy land with the Bruins at pick 14. We’re going to go ahead and draft Charles again. The Bruins also have the 29th pick courtesy of the Sharks and the Martin Jones trade (lol, remember when people wanted the Bruins to keep him and trade Tuukka? Yikes.) Trent Frederic has a certain degree of modest promise. The pick was panned at the time, but he’s developed into a solid prospect. However, he’s not going to help the Bruins win the 2020 Stanley Cup. 10 picks later, the Blackhawks drafted Alex DeBrincat, and he might be the third-line right wing on a Cup team.

David Backes
David Backes explains to the media that he would have signed with the Bruins, but he couldn’t outsmart their GM

Krug extends for four years, $21 million, but, more importantly, David Backes signs somewhere the hell else for way too much money. Later in the offseason, Marchand extends for eight years, $49 million, which will never not be awesome.

The promising roster I’ve crafted is underperforming. Since it couldn’t possibly be my fault, I make the decision to fire Claude Julien. I name Bruce Cassidy his successor. No interim tag. I just feel like he has what we need.

The 2017–18 Season

We’re getting there. We’ve laid the groundwork, so we need to figure out how to round out the roster. The draft is becoming less important as we get closer to 2020, so we’re going to go with whoever is most NHL-ready. Robert Thomas, taken just two picks after the Bruins drafted Urho Vaakanainen, fits the bill. He could fit smoothly on the third or fourth line in about a year, and I didn’t just pick him for the Matchbox Twenty jokes.

Tanner Pearson agrees to a four-year, $15 million extension. Along with some other small moves, I manage to ink Pasta to a six-year, $40 million contract. I call up every GM, one at a time, and tell them the good news. The other GMs hate me now, but I don’t care. I’m here for a good time, not for a long time.

At the deadline, we stand pat and move forward with Frank Vatrano and Ryan Spooner instead of Rick Nash and Tommy Wingels. We still lose to the Lightning in the second round, but I saved us a bunch of draft picks. The picks don’t matter that much for this, but I still want to be known as the greatest GM of all time after I retire in the 2020 offseason.

The 2018–19 Season

We start off by extending Seguin. He’ll get eight years, $78.8 million starting next season. Chara signs for one year at $5 million because we have the money, and he’s still useful. Then, we use our newly regained pick in the 2018 draft to take Rasmus Sandin—partly because he’s close to NHL ready, but mostly so that Toronto can’t have him.
I decide not to commit $13.75 million to John Moore—call it a gut feeling. In desperate need of a dependable backup goaltender, we snag Jaro Halak for two years, $5.5 million. We also take this time to re-sign Kuraly because I think he’s a tremendous fourth-line center.
I like Chris Wagner, but the depth we have would put him in the pressbox at best. He deserves better than that, and I’m a nice guy, so he signs elsewhere. Joakim Nordstrom also finds a different home.
Midseason trades for Charlie Coyle and Marcus Johansson get us heartbreakingly close to the promised land, but we’re still not quite there.

The 2019–20 Season

As we head into this offseason, I explain to Chara that we simply don’t have the money to bring him back. He gracefully retires, and in a touching ceremony, he bestows the captaincy upon Bergeron. I cry a bit, but not quite as much as if I were watching Pixar’s Coco—that would be unprofessional. Anyway, after a handful of depth signings, the roster looks like it belongs in the Louvre:


Brad Marchand – Patrice Bergeron – David Pastrnak

Tanner Pearson – Tyler Seguin – Mat Barzal

Anders Bjork – Charlie Coyle – Alex DeBrincat

Danton Heinen – Sean Kuraly – Rob Thomas from Matchbox Twenty


Thomas Chabot – Dougie Hamilton

Torey Krug – Chuck McAvoy

Matt Grzelcyk – Brandon Carlo


Tuukka Rask

Jaro Halak

Yeah, But What Happens Next?

The Bruins win the 2020 Stanley Cup. I immediately retire and hand the reins off to some Harvard guy named Don Sweeney. He’s pissed because there’s literally no possible way to negotiate extensions with all of the young players coming off their ELC and still stay under the cap. I say, “Hey, that’s your problem, pal.” as I pack my eight seasons of elite NHL GM salary in my Maserati and go back to my beachfront property on the Cape.


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s