Zak Krill/NHLI via Getty Images

Remembering The Worst NHL Trade Deadline Heists In the Last Decade

Lyle Fitzsimmons

The devil is in the details. Sometimes.

Though the NHL's trade deadline headlines are made by high-profile players being shipped to bolster playoff runs, it's just as often that winners and losers at the annual player-moving frenzy are determined by the draft picks and prospects included in those deals.

Which makes critiquing those transactions both a short- and long-term process.

Sometimes it's a win because the main player involved was the key to a successful championship chase. For others, it's because someone included on the laundry list of prospects and picks going the other way turns into an impact player in his own right.

Fortunately, the B/R hockey team is in prime condition now that the 2024 deadline is less than a week away and has focused its energies on looking at trade deadline moves from the last decade (2014 to present) to determine which swaps were the most one-sided.

Take a look at what we come up with and drop a thought of your own in the comments.

8. Edmonton Oilers Get Mattias Ekholm

Andy Devlin/NHLI via Getty Images

Score one for recency bias. And another for future possibilities.

Both are factors in including the 2023 deal that saw the Edmonton Oilers pluck defenseman Mattias Ekholm and the three years remaining on his contract from the Nashville Predators for Tyson Barrie and two draft picks, including their first-rounder last summer.

A steep price? Absolutely.

But it was a vital title-window piece for an Edmonton team starved for a steady defensive presence and it's paid off a season later with the emergence of Ekholm's primary blue-line partner, Evan Bouchard, into one of the league's top offensive defensemen.

And if the Oilers hoist the Cup this spring, it looks even better.

Barrie, meanwhile, is in the final year of a contract and is the subject of rumors again this time around, while Schaefer had 14 points in 46 AHL games this season. The first-round pick, No. 24 overall, was used to select Tanner Molendyk, who turned 19 in February and spent the season playing junior hockey in Saskatchewan.

7. Carolina Hurricanes Land Brady Skjei

Josh Lavallee/NHLI via Getty Images

Another deal. Another defenseman.

Former first-round pick Brady Skjei was in his fourth full season with the team that drafted him, the New York Rangers, when the Carolina Hurricanes came calling at the 2020 deadline and pried him loose from Broadway for a first-rounder in that summer's draft.

Like Ekholm before him, Skjei had become established as an all-around blue-line presence and had four years remaining on a contract that'll actually be expiring this summer.

He scored 10 points in 52 games in his first "full" season with Carolina, went to 39 and 38 in the next two, and is on pace for a career-high 45 this season. He's been a plus player in every season since the trade and is second on the team in ice time at 21:15 per game.

Perhaps the only knock from the Raleigh side is that the deal hasn't yielded a Stanley Cup, but the Hurricanes will again reach the 2024 playoffs as a favorite in the Eastern Conference.

The Rangers flipped the first-rounder they acquired from Carolina to Calgary and moved up in the draft to select defenseman Braden Schneider, who's produced 44 points in 184 games with New York across parts of three seasons.

6. Pittsburgh Penguins Swipe Justin Schultz

Jeanine Leech/Icon Sportswire via Getty Images

It's been a while, so you may forget about Justin Schultz.

He signed with Edmonton after a prolific college career at Wisconsin and was an early success in Alberta, making the league's All-Rookie team in 2013 with a pre-McDavid Oilers team that was in the midst of a dark decade and finished 24th overall.

It didn't get much better in northern Alberta as the group remained near the bottom of the Pacific Division in 2014 and 2015, but Schultz's power-play prowess was noteworthy and the Pittsburgh Penguins made him a target at the 2016 deadline, ultimately swinging a deal with the Oilers that cost only a third-round pick in that summer's draft.

To say it was an immediate success in Steel Town is to undersell it just a bit.

The Penguins won back-to-back Stanley Cups in 2016 and 2017 with Schultz producing 17 points in 36 playoff games, including three goals and seven assists on the power play.

He remained with Pittsburgh through 2019-20 and has played with Washington and Seattle since. Meanwhile, the player Edmonton drafted with the acquired pick, Filip Berglund, has never played in the NHL, peaking with 56 games with Bakersfield in the AHL in 2021-22.

5. Boston Bruins Acquire Charlie Coyle

Fred Kfoury III/Icon Sportswire via Getty Images

Let's say you're an NHL GM.

A colleague rings you up and says he'll offer a guy who grew up rooting for your team and played college hockey in your city, and all it'll cost you is draft pick and a player who's barely scraped your lineup while playing 46 games across two seasons.

If you're Boston's Don Sweeney, you take it.

And that's what the Bruins did in 2019 when they sent center Ryan Donato and a fifth-round pick to the Minnesota Wild in exchange for center Charlie Coyle, who's since climbed the depth chart to become their top-line center between Brad Marchand and David Pastrnak.

Coyle had been a solid performer with the Wild, reaching double-digit goals six times in their uniform but he's been better in Boston, where his performance through 61 games has him on pace for career-highs in both goals (28) and assists (39).

Donato spent one full season in Minnesota and scored 14 goals before leaving via free agency and signing with Seattle the following summer. He's now in Chicago and getting third-line minutes as a left winger. And the draft pick was flipped in a later trade.

As for the Wild GM, Paul Fenton, who engineered the deal? He was fired 160 days later.

4. Philadelphia Flyers Snatch Owen Tippett

Joel Auerbach/Getty Images

There are a lot of reasons to duck in Philadelphia.

Among them, saying the name "Chuck Fletcher" to a Flyers fan.

The veteran NHL executive had a nondescript run as the team's ninth GM from 2018 to 2023, but it wasn't without its triumphs.

Facing another bout of late-season irrelevance in early 2022, Fletcher looked toward the future and bit the bullet, sending franchise centerpiece Claude Giroux to Florida with two players and a pick in return for a haul that included two picks and Owen Tippett, whom the Panthers had chosen 10th overall in 2017.

The deal came two days after Giroux played his 1,000th game in a Flyers uniform and was met with predictable outrage, but the farther it gets into the rear-view mirror the better it looks for the black and orange.

Giroux was productive in the late season in metro Miami but didn't deliver the would-be playoff run, instead producing eight points in 10 games on the way to a second-round exit and subsequently bolting for a big-ticket deal with Ottawa as a free agent.

Tippett, meanwhile, has developed into the talent the Panthers thought they'd drafted, scoring 27 goals in his first full season with Philadelphia in 2022-23 and maintaining a pace this season that'll get him to a career-high 30 by the end of this season.

And lest anyone forget, the Flyers still have Florida's No. 1 pick in the 2025 draft.

Fletcher was fired last March.

3. Los Angeles Kings Get Marian Gáborík

Harry How/Getty Images

When a deal's immediate aftermath is a Stanley Cup win, it's a coup.

The Los Angeles Kings pulled one off at the deadline 10 years ago when they fetched Marián Gáborík, a 13-year veteran and three-time 40-goal man, from the Columbus, where he'd spent one season after a 2013 deadline deal brought him from the New York Rangers.

The move to the west coast came in exchange for Matt Frattin and two picks and Gáborík's presence was instantly felt to the tune of 16 points in 19 regular-season games and another 22 points (including a league-high 14 goals) across 26 playoff games as the Kings captured their second championship in three seasons.

Ironically, the title came against the Rangers in a five-game series.

The Slovakia native stayed in Los Angeles through the 2018 deadline when he was sent to Ottawa and finished his career with 16 games for the Senators.

Frattin played just four games with Columbus and 145 overall in an NHL career that ended with a stint in Toronto in 2014-15, and the Blue Jackets flipped each of the picks in other deals.

2. Dallas Stars Find Jake Oettinger

Sam Hodde/Getty Images

Remember what we said about details? Here's an example.

The Dallas Stars were in a brief downturn in the 2016-17 season on the way to missing the playoffs, so it was with an eye on the future that they sent productive winger Patrick Eaves, who had 21 goals and 37 points in 59 games, to the Anaheim Ducks.

The Ducks sent a conditional pick in that summer's draft as payback for Eaves.

And that's where it gets good.

The pick was based on Anaheim's performance in those playoffs and to what degree Eaves participated. If the Ducks made the Western finals and Eaves played in 50 percent of the games on the wat, the pick was ticked up to a first-rounder.

They did. He did. And a franchise's fortunes changed.

Anaheim played 11 games while beating Calgary and Edmonton in the first two rounds and Eaves played in seven, which meant the Stars would pick 29th in the first round in the Ducks' slot. GM Jim Nill then swapped slots with the No. 26 Chicago Blackhawks, sending the pick to the Windy City and selecting, wait for it...Jake Oettinger.

Yes, that Jake Oettinger.

The one who won his 100th career game on Thursday.

The one whose win total since the start of 2021-22 is sixth in the league. The one whose goals-against average in that same time stretch is tied for fourth. And the one who, if the Stars continue to maintain their place among the Western elite, has a real chance to be playing championship-contending games come May and June.

1. Vegas Golden Knights Grab Mark Stone

Ethan Miller/Getty Images

It's good to be an incumbent.

Because, on lists like this, it breaks a lot of ties.

Though some could argue Oettinger or Gáborík as more worthy, the fact that the Vegas Golden Knights hoisted the Stanley Cup last spring and captain Mark Stone was the first player to lay his hands on the silver chalice made the final call easy.

Now 31, the Winnipeg native was drafted and began his career with the Ottawa Senators, establishing himself as a two-way player and scoring 26 goals in 2014-15 and adding 28 across 59 games to start 2018-19 when the call came from the Vegas Golden Knights.

He headed to the desert along with Tobias Lindberg for a package that included Erik Brannstrom, Oscar Lindberg and a 2020 draft pick. An eight-year, $76 million contract guaranteed he'd be there for a while and he had 20-plus goals and 60-plus points for two straight seasons before a troublesome back nearly halved his 2022-23 season.

Stone came back for the playoffs, though, and was a gritty spark plug leader while producing 11 goals and 24 points in 22 games to give the franchise its first championship banner.

On the flip side, Lindberg hasn't played in the NHL since his 20-game stint for the Senators to end 2018-19, Brännström is averaging around 16 minutes for them this season and the draft pick, Egor Sokolov, has played 13 total games and none this season.

   

Read 29 Comments

Download the app for comments Get the B/R app to join the conversation

Install the App
×
Bleacher Report
(120K+)