The Chiarelli Cup: Which GM can make the best starting roster from players they've traded away?

Last week we tried to figure out the identity of NHL history’s most entertaining trader by assembling starting lineups based on players a single GM had traded for. Once we rigged the rules to keep Sam Pollock from rolling over the competition, it turned out to be a tight race.

But plenty of you had the same request: Now do it for players a GM had traded away. Or, as we took to calling it in the comment section, The Chiarelli Cup. OK, the customer is always right. You get your wish. Let’s do this.

A few notes before we get to the teams. First, we’re working with slightly different rules than last week. We’ll keep the Sam Pollock rule – the player himself has to be in the trade, not the draft pick used to select him. But last time, we were only giving GMs credit for what a player did on their team. Today, we’re giving credit for everything a player did in their career after the trade. So in theory, today’s rosters should be slightly better than last week’s.

It’s also worth pointing out that the easiest way to make the cut on a list like this is to have lots of trades to work from. Somebody who was only a GM for a few seasons just isn’t going to have the body of work to compete with somebody who was around for three decades (well, with one exception that we’ll get to). So this doesn’t actually end up being a list of history’s worst GMs like you might think. Guys who are widely considered to have been poor traders, like John Ferguson Jr., Réjean Houle or Mel Bridgman don’t show up here. They didn’t keep the job long enough and didn’t have enough talent to work with when they did.

And here’s one final note: There shouldn’t actually be any suspense here, since the answer is actually kind of obvious. Or at least, it should be. But maybe it isn’t, because of all the names I saw thrown around last week, almost nobody mentioned the actual frontrunner. So let’s see if you can figure it out before we get to the end of the list.

But we’ll begin at the beginning, with the man this exercise was named after.

Team Peter Chiarelli

Goalie: Tim Thomas

Defensemen: Johnny Boychuk, Justin Schultz

Forwards: Taylor Hall, Tyler Seguin, Phil Kessel

It’s a solid group. That forward line is a killer and we could follow it up with a second unit that includes Jordan Eberle and Blake Wheeler. There’s depth all up and down the roster, to be honest, and the Pollock rule means we’re not even giving credit for the Mathew Barzal pick here. But the starting blueliners are just OK and the goaltending isn’t great – Thomas should barely even count, since he was traded to the Islanders, never played and then left as a free agent before playing one more decent NHL season.

So Chiarelli’s not bad. But we can definitely do better. Let’s try the other name that probably popped into your head as soon as you heard the concept.

Team Mike Milbury

Goalie: Roberto Luongo

Defensemen: Zdeno Chara, Darius Kasparaitis

Forwards: Ziggy Palffy, Olli Jokinen, Todd Bertuzzi

Even without quite as much star power up front, this team beats Chiarelli’s pretty easily. It’s more balanced, with first-ballot Hall of Famers in goal and on the blueline. And it’s deep too, with names like Chris Osgood, Mathieu Schneider, Bryan McCabe, Bryan Berard, Michael Peca and Wendel Clark available.

Maybe even more impressively, it’s not like Milbury builds this roster by swinging high-profile but well-balanced blockbusters like some of his colleagues – he lost pretty much every trade that leads to that starting six. And you could make a strong case that we should waive the Pollock rule for Jason Spezza, since Milbury traded the second-overall pick on draft day and it was well-known at the time who the Senators would be using it on. We won’t do that here – rules are rules – but we all know what’s up.

So with apologies to its namesake, it’s Milbury who stakes out the early leader status for the Chiarelli Cup. But the competition is about to heat up.

Michael Martin/NHLI via Getty Images

Team David Poile

Goalie: Devan Dubnyk

Defensemen: Larry Murphy, Seth Jones

Forwards: Mike Gartner, Dino Ciccarelli, Jason Allison

Yikes. This loaded lineup is basically the anti-Milbury team; Poile did well on several of these trades, but has always been willing to give up something to get something. Still, that’s three Hall of Famers from his Washington days, plus two current all-stars – not to mention Shea Weber, who you could swap in on the blueline if you wanted. The third forward is really the only iffy spot, as Allison edges out a three-way Matt Duchene deal that only kind of counts.

The Dubnyk deal is a little bit of a sneaky addition, since he was barely considered an NHLer at that point and was basically given away to Montreal for nothing in return. Still, it counts, and based on his career resurgence in Minnesota it gives Team Poile a potential goaltending controversy with guys like Byron Dafoe and Tomas Vokoun. And as a side note, the Pollock Rule comes into play yet again, and it keeps a couple of big-name draft picks out of the Team Poile lineup: Joe Sakic and Erik Karlsson.

And just like that, I think we’ve got Milbury beat. With the two early favorites already out of the running, let’s see if we can find someone to challenge Poile.

Team Mike Keenan

Goalie: Dominik Hasek

Defensemen: Steve Duchesne, Dave Manson

Forwards: Brendan Shanahan, Denis Savard, Peter Nedved

Keenan’s another GM who falls into the Poile category: He was an aggressive trader who wasn’t afraid to move a big name out the door to get one back. For example, he won the trades that cost him Savard and Shanahan, turning them into Chris Chelios and Chris Pronger. The one trade he most certainly didn’t win was the infamous Dominik Hasek deal, which gives him the best goaltending of any team we’ll find. (And he can backup Hasek with Roberto Luongo and Curtis Joseph.) We also have to award a few bonus points for the Nedved trade, which Keenan was forced to make as a result of his own contract shenanigans.

Maybe Keenan can send one of those goalies to a guy who always seems to need one…

B Bennett/Getty Images

Team Brian Burke

Goalie: Kevin Weekes

Defensemen: Anton Stralman, Francois Beauchemin

Forwards: Pavel Bure, Sergei Fedorov, Alexander Mogilny

Burke’s squad actually isn’t as strong as you might think; I’m mainly including it because it’s kind of cool that he can lay claim to all of that famous line from the 1989 WJC. His blueline is OK, but the goaltending can’t compete with most others. (This is where fans of Burke’s various NHL teams will make a joke about him never having had a good goaltender to trade away.)

You’ll notice that we’re hitting on a lot of the same names as last week’s post here. That’s to be expected, since both the “traded for” and “traded away” lists are going to be focused on guys who had long careers. But for our next few slots, let’s mix it up with some names we didn’t see last time.

Team Neil Smith

Goalie: John Vanbiesbrouck

Defensemen: Sergei Zubov, Aaron Miller

Forwards: Doug Weight, Tony Amonte, Luc Robitaille

Smith did plenty of wheeling and dealing to build the 1994 Rangers and it paid off with a Cup even as guys like Weight and Amonte went on to become stars elsewhere. I’m guessing Rangers fans don’t mind. Robitaille only counts for 1998 and beyond, but that still ends up being over 200 goals, so he beats out a young Marc Savard for the last forward spot.

By the way, you may be surprised to see Vanbiesbrouck show up, since most of us remember him going from New York to Florida via the expansion draft. And he did – but first, Smith traded him to the Canucks so they could meet the exposure requirements. So it’s a bit of a technicality, but it counts.

Here’s another name we didn’t hit on last week, but who can put together a surprisingly solid roster despite only ever holding down the GM’s job once.

Team Darcy Regier

Goalie: Dominik Hasek

Defensemen: Brian Campbell, Keith Ballard

Forwards: Michael Peca, Thomas Vanek, Pat LaFontaine

Team Regier does better on initial name value than actual quality – he’s only getting one point-per-game year out of LaFontaine and his version of Hasek can’t hold up to Keenan’s. Still, it’s a decent squad, and one that reminds us what can happen when economics force a GM to take a scalpel to a very good team.

And speaking of which, we may as well get this out of the way…

Marc DesRosiers-USA TODAY Sports

Team Pierre Dorion

Goalie: Mike McKenna

Defensemen: Erik Karlsson, Ian Cole

Forwards: Mark Stone, Matt Duchene, Kyle Turris

Good lord, that was depressing. And the second forward line is Mika Zibanejad, Mark Hoffman and Ryan Dzingel, with Derick Brassard available for depth. Dorion has been the GM in Ottawa for less than three years, in case you were wondering. Any Senators fan in attendance at the last home game this year should be nominated for the Masterton.

And let’s finish off the theme of dismantling with one more contemporary GM who comes at it from a slightly different angle.

Team Stan Bowman

Goalie: Antti Raanta

Defensemen: Dustin Byfuglien, Nick Leddy

Forwards: Artemi Panarin, Andrew Ladd, Brandon Saad

Not bad for a team that was still winning Cups through most of those moves. Decent depth, too, with Niklas Hjalmarsson and Teuvo Teravainen available. (And we’re not even counting Marian Hossa.)

But while Bowman and Dorion have decent rosters for an active GM, they’re not really challenging for the overall crown. So let’s dip back into the past and let some veteran heavyweights take us home.

Team Harry Sinden

Goalie: Bill Ranford

Defensemen: Ray Bourque, Glen Wesley

Forwards: Phil Esposito, Adam Oates, Mariusz Czerkawski

I’d argue that the big story with Team Sinden is that it’s pretty good, but not great. That’s amazing, considering he was the Bruins GM for nearly 30 years and was one of the very best rosters from last week’s “traded for” teams. Here, we have three Hall of Famers who had good years left, but all of them are traded away well past their prime and there’s nobody that really stands out as a massive mistake. The guy was good at this job.

We went back a few decades for Sinden. Let’s go back even further for our next team.

Bruce Bennett Studios/Getty Images

Team Jack Adams

Goalie: Glenn Hall

Defensemen: Red Kelly, Bill Quackenbush

Forwards: Johnny Bucyk, Ted Lindsay, Roy Conacher

Now that’s a team. Longtime Red Wings GM Adams can claim a starting lineup of six Hall of Famers, including guys like Hall and Bucyk that he traded before they hit their prime. He’ll be especially deep in goal, with Terry Sawchuk and Turk Broda also eligible for the roster.

So yeah, Team Adams is stacked. It’s almost certainly the best team we’ve found so far. But it won’t be the best overall, because that obvious choice is still looming out there. Have you figured it out yet? Probably, but if not you’ve got a few paragraphs to go as we work through some of the honorable mentions.

I nearly worked Bobby Clarke into the mix, thanks in part to an Eric Lindros/Mark Recchi combo up front and his forgotten stint in Minnesota that saw him trade Larry Murphy. But he doesn’t have much to work with in goal, so he’s relegated to near-miss status. So is Cliff Fletcher, whose team would start strong with Brett Hull but otherwise be made up mostly of big-name veterans he’d traded for, wrung the value out of and then recycled to some other team. Bob Gainey has two building blocks in Jarome Iginla and Ryan McDonagh, but it gets thin after that, while Lou Lamoriello and Ken Holland didn’t trade away as many guys as you might think. I was really hoping to honor Phil Esposito’s legendary trade-per-week output in New York, but he was more of a quantity over quality guy. And while I’m pretty sure I could piece together a decent roster for Craig Patrick, I have enough Penguins fans mad at me for leaving him off last week’s list and don’t need to double down with any perceived insults here.

Oh, and an honorable mention also goes to that one guy that you think should have been listed that you’re really mad about. He made the cut too. I think an editor must have chopped out that paragraph by accident, but he was totally there, I assure you.

OK, we’ve got one more GM to go, and it’s the big one. If you haven’t already, this is your last chance to figure out the winner on your own.

Last warning.

OK, here we go…

Team Glen Sather

Goalie: Grant Fuhr

Defensemen: Paul Coffey, Brian Leetch

Forwards: Wayne Gretzky, Mark Messier, Jari Kurri

Yeah, it couldn’t really be anyone else. The rapid dismantling of arguably the greatest dynasty of all-time fell on Sather’s shoulders, and his roster shows it.

And that’s even taking into consideration that this crew of Hall of Famers isn’t quite as impressive as it looks at first glance. Leetch only had two years left when he was traded and Kurri was never an all-star outside of Edmonton. Those are admittedly picks based on name value and you could swap in someone like Jason Arnott or Vince Damphousse or Steve Smith if you wanted.

But it really doesn’t matter, because Gretzky and Messier combine for two Harts, three Art Rosses and over 2,000 points just between the two of them. Mix in two-thirds of Coffey’s record-shattering career and a lot more post-Oilers success from Fuhr than you probably remember and Team Sather looks hard to beat. Maybe Team Adams gives them a few good games in the final, but I don’t think it’s enough.

See, Oilers fans? Peter Chiarelli may not have been able to win the big prize, but it wound its way back to Edmonton after all. Some organizations just have that winning culture, you know?

(Top photo: Brian Babineau/NHLI via Getty Images)