Biggest wins and whiffs of past five NHL trade deadlines

NHL insider Elliotte Friedman joins Lead Off to discuss the latest in any Taylor Hall trade rumours, why he thinks it will be hard for them to get a first round pick in return, and why he believes the Bruins might be a good fit.

The context of most NHL trade deadline conversations is the here and now. Who can put a team over the top? Which general manager can find the perfect finishing touch?

Whether a team making additions has legit Stanley Cup aspirations or is simply trying to solidify a playoff berth and maybe win a round or two, it’s only natural we focus most of our attention on the moves that either do or do not pay off in the weeks and months ahead.

Say this, though: some of the swaps made around the deadline have a long, long tail.

Because only one team wins the title each year, sellers stand a much better chance of being happy with deadline moves, even if it takes years to play out on that end. Still, while we certainly don’t get a Butch Goring-to-the-1980-Islanders swap every year, there are more than a few veteran pickups that really paid off down the stretch and into the second season.

Sign up for NHL newsletters
Get the best of our NHL coverage and exclusives delivered directly to your inbox!

NHL Newsletter

*I understand that I may withdraw my consent at any time.

With that in mind, we thought it appropriate to examine the past five trade deadlines (including, of course, the days and weeks leading up to the actual deadline day itself) and identify some wins, whiffs and even some rare win-wins.



Canadiens acquire Phillip Danault from Chicago
The Canadiens were in a freefall leading up to the Feb. 29 deadline in 2016. The Blackhawks were the defending champions and were loading up for what they hoped would be another run. The cost of adding fringe pieces Dale Weise and Tomas Fleischmann was Danault — who turned 23 two days before the swap — and a second-round pick the Habs turned into defenceman Alexander Romanov.

Oil up the ‘Big Rig’
Pat Maroon had four goals in 56 games for a really good Ducks team when Anaheim dealt him to Edmonton for AHLer Martin Gernat and a fourth-rounder. Suddenly, Maroon was skating beside rookie sensation Connor McDavid and popped eight goals in his final 16 contests. The real payoff came the following season, though, when Maroon’s big body and underrated hands provided a perfect left-wing compliment for gunners McDavid and Leon Draisaitl on the Oilers’ top line, as Edmonton made its first playoff appearance in a decade and came within one win of a 2017 conference final appearance.


Eric Staal flops on Broadway
The Rangers were coming off a Cup Final appearance in 2014 and a final-four showing in ’15 when they surrendered two second-round picks to get Staal from Carolina. Staal, 31 at the time, already appeared to be on the downside, but his three goals in 20 games with New York — followed by zero points during a five-game, first-round loss to the Penguins — were a big disappointment. He’s already got one goal in three games as a 2021 deadline pickup for the Habs, so hopefully his experience is a little more positive this time out.



Penguins bolster blue line with Ron Hainsey
Hainsey didn’t have an NHL playoff game to his name when he was dealt from Carolina to the Penguins for a second-rounder and C-level prospect Danny Kristo about a month before his 36th birthday. The American defenceman played 21 minutes a night down the stretch for Pittsburgh, then saw more ice time than every Penguins player except Brian Dumoulin in the post-season as the Penguins won their second straight Cup.

Tampa exploits off-year with shrewd sell
This was an odd season for a Bolts team that entered the year with high expectations. Injuries whacked the club — Steven Stamkos was limited to just 17 games — and while they were still on the fringes of the playoff scene in late February, the Bolts decided to sell on UFA-to-be goalie Ben Bishop, knowing Andrei Vasilevskiy was ready to be the No. 1. Tampa shipped Bishop to Los Angeles for a return that included Slovakian prospect Erik Cernak, who has been a steady member of the team’s blue-line crew since the 2018-19 season.

The Kings, interestingly, were also a bubble team that year and chose to go the other way, acquiring Bishop from Tampa and Jarome Iginla from the Colorado Avalanche. L.A. failed to crack the post-season, but “Iggy” scored six goals in 19 games — a 25-goal pace — in his final eight weeks as an NHLer at 39 years old.


Eaves lights it up for Ducks
Patrick Eaves was in the midst of a career year when he was shipped from Dallas to the Ducks about one week before the 2017 deadline. He caried his touch over to Orange County, netting 11 goals in 20 contests for Anaheim. The Ducks made the conference final that spring, but Eaves’ post-season was, unfortunately, cut short by injury. The Stars, meanwhile, acquired a first-round pick at the 2017 NHL Draft that wound up being turned into Jake Oettinger, who will be part of the team’s crease picture for years to come.

Livestream every game of the Stanley Cup Playoffs, blackout-free. Plus get the NHL Draft, Free Agency, Blue Jays & MLB, NBA Playoffs matchups and more.



Jets snag Paul Stastny
The Jets made a big move to fill their second-line centre hole and, boy, did they find the right guy with Paul Stastny. It cost Winnipeg a first-round pick, but St. Louis also ate half of the money left on Stastny’s expiring deal. The crafty pivot was a perfect veteran presence between youngsters Patrik Laine and Nikolaj Ehlers, netting 13 points in 19 games with the Jets. Things got even better in the second season, as Winnipeg hosted its first-ever conference final series thanks in large part to the 15 points in 17 games Stastny produced. No wonder both parties were happy to re-unite before this season following Stastny’s two-year sojourn in Vegas.

Sens land valuable futures
The three-way swap between Ottawa, Pittsburgh and Vegas had a lot of moving parts — complete with some salary retention — but the bottom line was, basically, the Senators moved off disappointing Derick Brassard and wound up with a first-round pick they turned into defenceman Jacob Bernard-Docker and goalie prospect Filip Gustavsson. After three NCAA seasons at North Dakota, Bernard-Docker just signed his entry-level deal with the Sens and will carry high hopes into the pros. Gustavsson, 22, has played his first four NHL games this season and posted a .946 save percentage.

Coyotes net a keeper in Darcy Kuemper
Nobody paid much attention when Arizona sent depth scorer Tobias Rieder and goalie Scott Wedgewood to the Kings for Darcy Kuemper. The former had played well in L.A. but was the odd man out in a crease scene that also included Jonathan Quick and Jack Campbell. Kuemper has now played 112 games for Arizona and posted a .922 save percentage. The only issue is the six-foot-five puckstopper just can’t seem to stay healthy.

Capitals finally find their man in Michal
Who knew the missing piece in Washington’s decade-long search for the championship mix was an overlooked defenceman playing barely 15 minutes a night for the Chicago Blackhawks? OK, maybe it’s a stretch to say Michal Kempny put Washington over the top, but nobody could have guessed he’d play such a valuable role for the title-winning Capitals, getting top-four minutes playing next to John Carlson in the playoffs. All it cost the Capitals was a third-round pick.

Colorado kills it in swap of AHLers
The Avs were on their way to a surprise playoff appearance when they swung a minor deal to nab defenceman Ryan Graves from the Rangers for blue-liner Chris Bigras. Graves, a fourth-rounder in 2013, didn’t play a game for Colorado that year, but has become a valuable member of Colorado’s top-four and averages nearly 20 minutes a night for the Avs. Bigras, a second-rounder in 2013, has not played an NHL game since the season this swap was made.

Kane do in San Jose
Man, 2018 was a great year to make a deadline deal. So much has gone wrong in San Jose the past few years that it’s easy to forget getting Kane from Buffalo really was a coup. The Sharks forked over a first-rounder, but Kane — who signed an extension to remain in San Jose that spring — has scored 81 goals in 194 contests with the Sharks, 12 more than anybody on the team during that time.


Tatar leaves his sauce in Detroit
One year after making the Stanley Cup Final as a first-year team, Vegas got very aggressive at the deadline. The Golden Knights handed Detroit a 2018 first-, 2019 second- and 2021 third-round pick for Tomas Tatar, who was in the first year of a four-year contract. Tatar scored just four goals for Vegas in 20 games and was even a healthy scratch for the Knights in the playoffs. The team had to retain some of his salary when he was moved at training camp the next year in the deal that landed them Max Pacioretty from Montreal.

Rick Nash less than golden with B’s
It’s not like the Bruins thought they were acquiring a 50-goal man when they brought in 33-year-old Nash, but they were probably hoping for more after sending a first-round pick the New York Rangers’ way. Wearing the Black and Gold, Nash netted three goals in 11 regular-season games and three more in 12 post-season contests as the Bruins were bounced in Round 2. Those wound up being the final outings of his NHL career.



Columbus goes crazy
Forget who has what Cups on his resume; is there a more ‘OG’ GM than Jarmo Kekalainen? He basically won the hearts of everyone in hockey when he mainlined the fundamental spirit of pro sports — “Hello! You play to WIN the game!” — and went all the way all-in with a playoff-bubble Blue Jackets team that was still in search of its first post-season series win in franchise history.

Not only did Kekalainen trade for Matt Duchene, Ryan Dzingel, Keith Kinkaid and Adam McQuaid, he also hung on to UFAs-to-be Sergei Bobrovsky and Artemi Panarin despite the fact we all knew they were headed for sexier living situations. Columbus squeezed into the playoffs and, of course, shocked the league-leading Tampa Bay Lighting with a sweep in Round 1, then showed well in a six-game loss to the eventual Eastern Conference champs in Boston. Duchene’s playoff stat line was 5-5-10 in 10 outings and Bobrovsky posted a .925 save percentage. The fact everyone blew town after the playoffs doesn’t diminish Kekalainen’s work one bit.

Vegas locks up Mark Stone
Sometimes you shop for bargains, other times you shell out for the sure thing. The Golden Knights acquired Mark Stone from Ottawa on Feb. 25 and officially put pen to paper on an eight-year contract extension about two weeks later. Before this season, he was named the first captain in team history. Erik Brannstrom — the biggest piece in the return — may wind up becoming a great offensive defenceman for Ottawa, but this was a no-brainer for Vegas.

Minnesota takes a flyer on Kevin Fiala
Paul Fenton’s one-year term as Wild GM will likely be largely forgotten, but one move that could keep “State of Hockey” residents warm for many winters to come was landing Fiala from Fenton’s old employer, the Nashville Predators. The Wild gave up a quality player in Mikael Granlund to get him, but the younger Fiala has finally made good on his 11th-overall (2014) potential with the Wild. The 24-year-old has played at a 30-goal, 65-point pace since the start of 2019-20 and, though he needs a new contract this summer, he’s still a restricted free agent.

Boston brings Charlie Coyle home
The local kid took a while to get going once he got to Massachusetts from Minnesota, but Coyle was a huge contributor in the second season, notching nine goals and 16 points in 24 playoff games as the B’s came within one home-ice win of capturing the 2019 Cup. It doesn’t hurt that all Boston surrendered was Ryan Donato and a fourth-rounder to get Coyle, who also signed an extension late in 2019 that will keep in Boston for a long time.

Maple Leafs acquire Muzzin from Kings
A Buds blue line that needed help got just that in the form of steady, battle-tested Jake Muzzin from the Kings. Toronto GM Kyle Dubas got in front the market, acquiring Muzzin about a month before the deadline. The fact Muzzin signed an extension before becoming a UFA in 2020 makes this a clear victory for the win-now Leafs, even if it cost a first-rounder and quality prospect in defenceman Sean Durzi.

Jeff Marek and Elliotte Friedman talk to a lot of people around the hockey world, and then they tell listeners all about what they’ve heard and what they think about it.



Carolina takes advantage of Panthers’ goof
Fourteen months later, we’re still at a loss for why Florida just seemed to give away Vincent Trocheck, sending him to the Canes for a big bag of nothing. This was the rare deal that, even in the minute, you just couldn’t wrap your head around. Sure, Trocheck had his battles with injuries, but it was just so clear to see how he could be a perfect No. 2 behind Aleksander Barkov. Instead, he’s a fantastic second-line centre in Carolina behind Sebastian Aho. The two are leading the Canes with 16 goals apiece this year and Trocheck — despite once again missing a few games — is second in team scoring behind Aho with 33 points in 30 contests.

Tampa’s final touches
With its shocking sweep at the hands of Columbus still fresh in peoples’ minds, Tampa went out with a clear mandate to add toughness at the 2020 deadline. Enter Barclay Goodrow from San Jose and Blake Coleman from New Jersey, both of whom played significant playoff minutes for the team during its march to the Bubble Championship late last summer.

Leafs find a backup — who is now the starter
Dubas went back to the well, dealing with L.A. for the second year in a row to acquire Jack Campbell and gritty winger Kyle Clifford. This trade was a win when Campbell came in and played .915 goal behind Frederik Andersen for six games last spring. It’s something more than that now as Campbell — with Andersen injured — is among the best puckstoppers in the league for a Toronto squad chugging toward a North Division crown.

Vegas crowds the crease with Robin Lehner
Though the three-way deal that put Lehner in Vegas created a bit of an awkward situation with franchise face Marc-Andre Fleury, the Golden Knights are always swinging for the fences and Lehner has been one of the league’s best goalies the past few years. Though Fleury came flying out of the gates, he’s struggled recently and Lehner figures to be the man when the playoffs roll around.


Ondrej Kase a no-show for the Bruins
Acquiring a 24-year-old, controllable asset with scoring touch seemed like a great idea for the Bruins, who handed a first-round pick over to the Anaheim Ducks to get Kase. Unfortunately, his time in Boston has been an unmitigated disaster. Kase was on the dreaded “unfit to play” list as the B’s prepared to travel to the Toronto bubble, then scored zero goals in 11 post-season games once he joined the team. He has not played since Boston’s second game of the year this season and the team is not being transparent about what’s ailing the Czech.

When submitting content, please abide by our submission guidelines, and avoid posting profanity, personal attacks or harassment. Should you violate our submissions guidelines, we reserve the right to remove your comments and block your account. Sportsnet reserves the right to close a story’s comment section at any time.