6Roberto Luongo to Toronto
It's hard to say how Roberto Luongo would have fared in Toronto if this deal had gone through. On one hand, the pressure of playing in Vancouver–a smaller and less intense market than Toronto—seemed to get inside Luongo's head, but on the other hand, he's one of the best goalies of his generation and does have a history of pulling through in the clutch.
We'll never know what Toronto offered for Luongo in the first place but it has been well-documented that in 2013, around the time of the NHL draft, the Toronto Maple Leafs had an offer on the table for the Vancouver netminder. No doubt in part because Dave Nonis, who'd been General Manager of the Canucks, was General Manager for the Toronto Maple Leafs.
Luongo rejected the trade to the Leafs because he'd heard through the grapevine that the Florida Panthers were also preparing an offer, this was more attractive to him because his family was based in Florida and he spent his summers there anyway. The trade to Florida ended up being for Jakob Markstrom—a serviceable goalie who isn't elite by any standards—and Shawn Matthias, who has been bouncing around the league in recent years.
5Tomas Vanek to Boston for Tyler Seguin
The Boston Bruins are one of the most resourceful and successful NHL teams of the last decade but that doesn't mean that they're immune from the sting of a bad trade. Three years after selecting Tyler Seguin second overall in the draft, they were unhappy with his production and decided to trade him to Dallas for a bunch of guys, including Loui Eriksson and Reilly Smith.
Now, five years after that trade, the Boston Bruins do not have a single player on that roster from that deal. Meanwhile, Seguin flourished in Dallas, becoming an elite-level talent who you can always count on for a point-per-game season.
Because the Bruins were so desperate to get rid of Seguin, they also almost traded him to Buffalo for Tomas Vanek, which would have been an equally disappointing deal.
While Vanek was a great, dynamic goal scorer for the Sabres early in his career, in recent years he has revealed himself to be a floater who takes games off and isn't really willing to contribute on the defensive end. Apparently, the Bruins were looking for another piece or two to bolster the trade, and the Sabres were unwilling to commit. It's interesting to think of how a guy like Seguin would have helped the development of the Sabres or how they may have stunted his career.
4Gabriel Landeskog To Boston for Brandon Carlo and More
This almost-trade is a good example of how quickly things can change in a year. Last year, the Colorado Avalanche had a terrible season and people were wondering how they could possibly get things back on track. The solution seemed to involve trading their captain, Gabriel Landeskog for some reason. They had a deal on the table to trade him to Boston in exchange for Brandon Carlo and another pick and prospect or two. Now, more than a year later, Brandon Carlo has failed to have any kind of real impact on an NHL level, whereas the Avalanche rapidly turned things around with Nathan MacKinnon this season establishing himself as one of the best players in the world and the Avalanche making the playoffs. He's quelling any feelings that they should sell the farm.
While it's certainly true that the Avalanche were outclasses by the Nashville Predators in the first round this year and never really seemed to have much of a chance of winning that series, it's clear now to Avalanche fans that the solution won't be found in trading key pieces away. They instead can slowly build towards a stronger future by continuing to add contributors to their already-solid core.
3New York Islanders Offer All Their 2012 Draft Picks for Ryan Murray
If you Google some combination of the phrases "Garth Snow" and "fired" you'll quickly see that there's a general sentiment around the league that he's made too many suspect moves for too long and some time soon the New York Islanders will have to cut ties with him, setting him free. He has also won awards for some surprisingly savvy moves, and it's hard to say whether his decision to offer every single one of the New York Islanders' draft picks in 2012 for the second overall pick—which he planned to use to draft defenseman Ryan Murray.
It might have been a solid move or another boneheaded wildcard decision.
One can argue that if you add up the average number of NHL games played by a second overall pick compared to every other lower pick from a lower-drafting team, you'd get more impact overall out of the second overall pick. That may be, but it's also true that going all-in on a single player is a risky proposition.
The 2012 NHL entry draft seems to be the weakest in recent memory, with a first round full of busts in Nail Yakupov, Griffin Reinhart, Derrick Pouliot and many more.
2Any Trade At All for Dan Hamhuis
Back around the time of the 2016 NHL trade deadline, Dan Hamhuis was one of the most sought-after defensemen on the market, and for good reason. He has a balance of good puck-moving ability with reliable defensive play, which made him a legitimate top-pairing d-man for years. He played on the top pairing in Nashville with Shea Weber, and on the top line in Vancouver with Alex Edler but when Vancouver became a team that wasn't making the playoffs anymore, it was clear that Hamhuis should be moved at the deadline. Both to give him a chance to win and to give the Canucks a decent return on such a key asset, lest he be lost for nothing to free agency.
A wide number of trades were discussed. Some of them, very optimistic on the part of Vancouver fans. It included Hamhuis being traded to a contender for a playoff run but then re-signing with Vancouver the next season. Other proposals involved picking up a draft pick or a prospect for Hamhuis, who is now 33.
However, in a stunning display of futility, the Canucks instead did nothing, allowing the Stars to sign Hamhuis to a very reasonable contract of less than $4 million per year without giving up any of their assets. The Hamhuis example provides a counterpoint to the overzealous trading teams out there. While there's no need to make a risky move just for the sake of it, you also have to know when it's foolish not to pull the trigger.
1Andrei Markov, Jose Theodore and Two First Rounders to Atlanta for Kovalchuk
This truly would have been one of the biggest trades in NHL history if you consider the impact all of the players involved had on the league. It's strange to think of the butterfly effect as it pertains to hockey and how the inclusion of a single prospect on a trade can shape an organizations' future. It's fair to ask, "Isn't this article about current players? Aren't all of these players not current NHLers?" And this is true, but perhaps not for long. There has been big time media speculation that Ilya Kovalchuk is eyeing a return to the NHL. He has been playing in Russia since 2013 but he has stated his interest in rejoining the New Jersey Devils, who own his rights in the NHL for the foreseeable future.
It's a little disingenuous to say that this package was offered for Kovalchuk, though. What happened was that at the entry draft in 2001, Canadiens' General Manager Andre Savard offered this combination of players for the first overall pick, which Atlanta used to draft Kovalchuk, who had an immediate impact in Atlanta. The deal was turned down because Don Waddell, the Thrashers' GM, wanted goaltender Mathieu Garon rather than Jose Theodore, though Theodore would go on to win both the Hart Trophy and the Vezina Trophy the very next season.
Meanwhile, Kovalchuk was kind of buried in the disinterested hockey market of Atlanta and it's interesting to think of how Habs fans would have responded to having a frequent 50 goal scorer in their lineup.