Let’s just come right out and say it: The General Manager of the Year is a weird award.

Oh, it’s a nice idea. If players and coaches can be honoured for a good season, then GMs should too. But the award, first introduced in 2010, has never really seemed to work. A GM’s job involves building a roster over multiple seasons, often through moves that don’t pay off until years down the line. Even if you wanted to honour the guy who had the best single season, you wouldn’t be able to know who that was without the benefit of hindsight.

Luckily, we have that hindsight available to us now. So today, let’s go back over the history of the GM of the Year trophy, and retroactively re-award it to the guy who actually deserved it.

First, a few ground rules. We’re looking at everything a GM is responsible for, including the draft, free agency and trades. We don’t care about anything that came before the season; you don’t get GM of the Year credit because a prospect you drafted three years ago had a great rookie year, or a guy you traded for the previous season had a breakthrough. We also don’t care about mistakes made in the future, so if you built yourself a nice little sand castle one year, you don’t lose points for kicking it over the next.

The standings matter, although not all that much because they’ll heavily reflect work that had been done in previous years. And the playoffs matter more, because it’s completely insane to create an award for the guys trying to build championship rosters and then vote on it before the post-season is even over. Which is what the league does, by the way.

Finally, we’re going to define the “season” as everything that happens in between Stanley Cup presentations. So from the moment the last chorus of boos reign down on Gary Bettman, NHL GMs are competing for next year’s award.

We’ve got six seasons to work with. Let’s go back and get it right.

2009-10

The actual winner was: Don Maloney of the Coyotes. (For the award’s first few years, no other finalists were announced.)

But in hindsight: Maloney didn’t really do much during the season beyond landing Radim Vrbata in a trade. The Coyotes did make the playoffs for the first time in seven years, but wouldn’t actually win a round until their deep run in 2012.

So on paper, this was an odd pick. But really, this was less about what Maloney did with the roster and more about everything he’d put up with over the years in Arizona. The team had just gone through a bankruptcy and was constantly rumoured to be on the verge of moving, so Maloney was managing with one hand tied behind his back. His colleagues apparently wanted to recognize that, which is probably as good a reason as any to hand out this kind of award.

It could have gone to: One of the strongest performances came from Greg Sherman of the Avalanche, and yes, I’m as surprised as you are. But the Avs had the league’s best draft, hitting hard on Matt Duchene third overall and Ryan O’Reilly at No. 33. Sherman also signed Craig Anderson as a reasonably cheap free agent, then saw him win the starter’s job while helping the team to a 26-point improvement in the standings.

There’s also a strong case for Paul Holmgrem, who got a Flyers team just three years removed from finishing dead last all the way to the Final, largely on the strength of an aggressive off-season trade for Chris Pronger. And Peter Chiarelli took a potentially disastrous Phil Kessel situation and turned it into a big win.

You could also make an argument for the Blackhawks, who won the Stanley Cup after landing the best UFA signing of the ’09 off-season in Marian Hossa. But that gets tricky, because this was the year that Dale Tallon was demoted in mid-July after mishandling the Hawks’ offer sheets, making way for Stan Bowman to assume the role.

Tallon deserves most of the credit for building those 2010 champs, but even in our alternate universe, giving the trophy to a guy who’d already been relieved of his duties seems like a stretch.

But the winner should have been: Glen Sather. The Rangers missed the playoffs for the first time in six years, but in hindsight Sather was laying the groundwork for the team that would emerge as one of the league’s best just a few seasons later. He hit on his first round pick, landing Chris Kreider at 19th overall in a first round that thinned out quickly after the first few picks. And he made a big splash in free agency by signing Marian Gaborik, who’d score 40 goals twice over the next three seasons and represent one of the few big-money free agent signings of recent years that actually worked out.

But Sather’s best move remains one of his most famous – the June, 2009 trade that sent Scott Gomez to Montreal for a package that included a young Ryan McDonagh. Given Gomez’s ridiculous contract, the deal seemed like a miracle for the Rangers at the time, and it only looks better in hindsight.

McDonagh may be the most valuable current Ranger apart from Henrik Lundqvist, and Sather landed him in a deal where he should’ve been giving the Habs young players just to take on dead money. That alone is enough to earn him some hardware.

2010-11

The actual winner was: Mike Gillis of the Vancouver Canucks

But in hindsight: Gillis gets the dubious distinction of being the real award’s first recipient to go on to be fired and remains the only past winner who isn’t currently holding down a GM job somewhere. Still, it’s not hard to see why he won – the 2010-11 Canucks were a fantastic team, one that ran away with the Presidents’ Trophy and came within one game of winning the Stanley Cup.

But virtually the entire roster came pre-assembled; Gillis did land free agent Dan Hamhuis on a nice deal, but until Alex Friesen debuted this week, the Canucks had yet to get a single NHL game out of their 2010 draft (largely because they traded each of their first three picks).

All that said, we’ll give Gillis some credit for his post-victory quote: “It’s great, I guess.“

The GM of the Year Award: Feel the excitement!

It could have gone to: Hurricanes’ GM Jim Rutherford nailed his draft, landing Jeff Skinner and Justin Faulk with his first two picks. Brian Burke did some reasonably decent work in Toronto, getting Clarke MacArthur on a bargain UFA contract and pulling off a pair of nice trades to land Jake Gardiner and Joffrey Lupul from Anaheim, then getting a first rounder from Boston for what was left of Tomas Kaberle. And Bowman gets another mention, as he guided the Cup champs through salary cap hell without crippling their chances for future success.

But the winner should have been: Doug Armstrong of the Blues. Sure, St. Louis missed the playoffs, making it the sixth straight year that they’d failed to win a single post-season game. But Armstrong pulled off a pair of big trades, getting Jaroslav Halak from the Canadiens and then robbing the Avalanche in the Kevin Shattenkirk deal.

And in the 2010 draft, he sent highly regarded prospect David Rundblad to the Senators for the 16th overall pick. Rundblad wasn’t a disaster for the Sens, who later flipped him to the Coyotes in the Kyle Turris deal, but he’s largely been a bust at the NHL level.

As for that 16th pick, Armstrong used it on a hot-shot Russian winger named Vladimir Tarasenko. That’s some impressive work. Give Doug Armstrong the GM of the Year, voting committee!

2011-12

The actual winner was: Doug Armstrong of the Blues. Hey, they retroactively listened to me! (Nashville’s David Poile and Florida’s Tallon were the other finalists.)

But in hindsight: The Blues made a big jump in the standings, and won a playoff round for the first time in a decade. But Armstrong didn’t really do all that much during the actual 2011-12 season – he gets points for signing Brian Elliott, but that created a goaltending backlog that later forced him to trade away a young Ben Bishop. The Blues draft didn’t bring much help, and other than signing a few veterans in free agency and a big mid-season coaching upgrade from David Payne to Ken Hitchcock, Armstrong’s Blues were mostly building off the groundwork he’d already laid.

It could have gone to: We’ll give Maloney a nod here for finding one of the few decent signings in a terrible UFA class in Mike Smith, who’d provide excellent value for two years before getting his current extension. Bowman had yet another strong year, unloading some bad contracts (including a Brian Campbell deal that had looked untradeable) and finding Brandon Saad in the second round.

And the much-maligned Jay Feaster era in Calgary had a surprisingly solid year in hindsight, as he traded for Mike Cammalleri and future starter Karri Ramo and hit a home run on Johnny Gaudreau in the fourth round of the draft.

But the winner should have been: Dean Lombardi of the Kings. Here’s a rule of thumb: when you make a gutsy blockbuster trade in the summer (Mike Richards) and another before the deadline (Jeff Carter) and then watch your team roll over everyone in the playoffs to win the franchise’s first Stanley Cup, you’re the GM of the Year.

Sure, the Kings draft and free agency wasn’t much to get excited about. And yes, the whole Richards thing ended badly years later. But the fact remains that Lombardi swung hard for the fences not once, but twice, and ended up with a Stanley Cup ring because of it. A league full of timid GMs who insist it’s too hard to make big trades in the cap era apparently slept through Lombardi’s 2011-12 work.

2012-13

The actual winner was: Ray Shero of the Penguins, over Montreal’s Marc Bergevin and Anaheim’s Bob Murray.

But in hindsight: To his credit, Shero made a pair of big trades, shipping out Jordan Staal at the draft and then adding Jarome Iginla in that bizarre trade deadline debacle.

That was part of a busy few days that saw the Penguins load up for a Cup run – unsuccessfully, as it turned out, thanks to a conference final sweep at the hands of the Bruins.

For what it’s worth, Shero would go on to become the first (and so far only) GM of the Year winner to be fired within a year of accepting the trophy.

It could have gone to: Sherman shows up here again; while the deal that sent a first round pick to the Capitals for Semyon Varlamov seemed like an overpay at the time, it’s worked out well for the Avalanche in hindsight. Caps’ GM George McPhee would get some love for that deal too, since he turned the first-round pick into future all-star Filip Forsberg, but… well, yeah.

Burke robbed the Flyers in the Luke Schenn–James van Riemsdyk trade and found Morgan Rielly in a very hit-and-miss first round, but we’ll have to disqualify him based on the whole “got fired before the season even started” technicality.

The same thinking takes care of Scott Howson, who was canned by the Blue Jackets midway through the year despite doing reasonably well on the Rick Nash trade and landing Sergei Bobrovsky and Nick Foligno in off-season deals. And Paul Holmgrem was all over the map, giving away Bobrovsky but then landing Steve Mason, and signing Shea Weber to a massive offer sheet that didn’t work but at least provided some fireworks.

But the winner should have been: This may be the toughest pick of the bunch, because this was a weird year. The lockout played havoc with both the 2012 off-season and the shortened regular season that followed – nobody wanted to make any major moves before the new CBA was in place, and there wasn’t time to get much done once it was. In fact, I’m really tempted to give this one to Bowman, not because he earned it – he was pretty quiet in another Cup-winning year – but because I’m dreading Hawks fans’ reaction once they realize he’s getting shut out in this post.

But instead, this year’s award goes to San Jose’s Doug Wilson, who managed the rare trick of pulling off a minor rebuild while still contending. He loaded up on draft picks by trading away Ryane Clowe, Douglas Murray and Michal Handzus, but still came within a win of going to the conference final. Factor in finding Tomas Hertl and Chris Tierney in the draft, and it’s enough to give Wilson the nod. (He also added Scott Gomez and Raffi Torres. Look, I said it was a weird year.)

2013-14

The actual winner was: Bob Murray of the Ducks, over Bergevin and Lombardi.

But in hindsight: Murray was a decent choice, although once again this felt like more of a lifetime achievement award than recognition of a single season of work. His biggest move was the Bobby Ryan trade with Ottawa, which holds up well in hindsight. Otherwise, it was a quiet year, as the Ducks team he’d built over the years rolled to a 116-point regular season before falling to the Kings in the second round.

It could have gone to: No team had a better year on the trade market than the Sabres, who scored a pair of big wins by dealing Tomas Vanek to the Islanders and Ryan Miller to the Blues. But those deals were split between two GMs, with Tim Murray taking over for Darcy Regier midway through the season.

For pure entertainment value, no GM had a busier year than Gillis, who traded both Cory Schneider and (eventually) Roberto Luongo before getting his pink slip at the end of the season. That Schneider deal also earns some consideration for Lou Lamoriello, who may even move to the top of the list if you also give him credit for “convincing” Ilya Kovalchuk to head back to Russia.

Lombardi scored another mid-season blockbuster with the Blue Jackets, this time for Marian Gaborik, and it led to another Cup ring. And Jim Nill very nearly takes the trophy solely on the strength of the Tyler Seguin robbery.

But the winner should have been: This is a tough call, but we’ll give it to Steve Yzerman, for three reasons. One, as we’ll see in the next section, we’re about to strip him of the 2015 award, and he’s having a tough enough month as it is.

Two, he managed to convince ownership to let him use a compliance buyout on Vincent Lecavalier, which was the most expensive of all-time, but gave the Lightning the cap flexibility to build (and maybe even keep) a championship-calibre roster. And three, he managed to take what should have been an impossible situation – franchise player Martin St. Louis demanding a mid-season trade, then using his NTC to name only one possible destination – and somehow managed to turn it into an impressive haul of Ryan Callahan and two first round picks.

Admittedly, Yzerman inherited some A+ pieces when he took the Lightning job. But the 2013-14 season presented plenty of opportunity for the whole thing to implode, and Yzerman stickhandled around those landmines brilliantly. Sometimes, that’s the most important thing a GM can do.

2014-15

The actual winner was: Yzerman, beating out Sather and Bob Murray.

But in hindsight: Yzerman made a few nifty moves to clear some cap space ahead of free agency, and the Anton Stralman signing may have been free agency’s best. But this was a relatively quiet year for Yzerman, and yet another case of the GM of the Year award going more for past work than for what had actually gone on during the season.

It could have gone to: With less than a year passed since this award was handed out, there’s not much hindsight to be had here, but we can still give credit to a few guys who didn’t even make the finalists list. Chuck Fletcher made what stands as the best trade of the year, saving the Wild’s season by landing Devan Dubnyk from the Coyotes. Garth Snow’s trade work on the eve of the season opener helped push the Islanders back into the playoff picture. And despite a fairly quiet year, Ken Holland deserves a mention for getting the steal of the draft with Dylan Larkin at the 15th pick.

But the winner should have been: Tim Murray. Look, we can argue over whether tanking should be a viable strategy in the NHL. But the reality is that it works, and with Connor McDavid and Jack Eichel on their way, this was the year to tank and tank hard. So Murray and the Sabres did. Allegedly.

Murray put together a solid 2014 draft around Sam Reinhart, then pulled off the season’s biggest blockbuster to land Evander Kane and Zach Bogosian. Even the Christian Ehrhoff buyout, which raised eyebrows at the time, ended up looking like the right move. He resisted calls to replace Ted Nolan during the season, which would eventually make it possible to lock down Dan Bylsma. And he made various small deals to turn veterans into draft picks, all without adding anyone who would actually help the Sabres win games in 2014-15. Which, again, was the season’s entire point.

Call it tanking or call it aggressive rebuilding, but the bottom line is that Murray came into the season with a plan, and he executed it to perfection. Sure, losing the draft lottery hurt – Murray even admitted as much – but Eichel was a heck of a consolation prize.

Hopefully, our alternate universe GM of the Year trophy helps a little too.