Ken Holland’s trade deadline history and what to expect from him this year

Cam Lewis
1 year ago
The trade deadline for the 2022-23 season is one month away.
The Edmonton Oilers entered the All-Star break having earned at least one point in eight consecutive games and they’re within reach of the top spot in the Pacific Division.
This hot streak has calmed the external pressure on general manager Ken Holland to make a move to spark the team but there are still expectations that he’ll make upgrades to the Oilers’ roster in order to help them go on a deep playoff run this spring.
Might this be the year that Holland makes the big splash that fans have been asking for? Let’s go through his history at the trade deadline in the salary cap era for clues on what to expect…

The 2005-06 Red Wings

Traded a fourth-round pick to the Penguins for Cory Cross. 
Before the 2004-05 NHL lockout, Holland could freely spend Mike Ilitch’s money to add star players pretty much whenever necessary. That all changed when the salary cap was implemented.
In his first season in the salary cap era, Holland was quiet at the trade deadline, only adding defenceman Cory Cross from the Penguins in exchange for a fourth-round pick. The Red Wings cruised to the top record in the league that season but wound up getting shocked in the first round of the playoffs by the Oilers.

The 2006-07 Red Wings

Traded Jason Williams to the Blackhawks for Kyle Calder. Traded Shawn Matthias and a second-round pick to the Panthers for Todd Bertuzzi. 
Holland was more aggressive at the following season’s trade deadline. First, he moved longtime Red Wing Jason Williams to the Blackhawks for Kyle Calder in a deal that freed up some cap room. After that, he made a pretty big splash, sending prospect Shawn Matthias and a second-round pick to the Panthers for Todd Bertuzzi.
The Red Wings wound up reaching the Western Conference Final that season but were edged out by the Anaheim Ducks in six games. Both Bertuzzi and Calder left the team in free agency that summer.

The 2007-08 Red Wings

Traded a second- and a fourth-round pick to the Kings for Brad Stuart. 
Detroit’s big add for the 2007-08 season came in the off-season when Holland signed Michigan native Brian Rafalski in free agency. Holland also added to the blueline ahead of the trade deadline, sending two draft picks to L.A. for veteran shutdown defender Brad Stuart.
The Red Wings went on to win the Stanley Cup that spring, taking down the Penguins in six games. Stuart logged 21:40 per game during their playoff run and he signed a four-year deal to stick around with Detroit in the off-season.

The 2008-09 Red Wings

Yet again the Red Wings’ big addition came during the off-season as they inked Marian Hossa to a one-year deal in free agency. Given that expensive signing and the assets that were given up over the previous two seasons, Holland stood pat at the trade deadline in 2008-09.
The Red Wings made it to the Stanley Cup Final again but this time the Penguins came out on top, winning the series in seven games.

The 2009-10 Red Wings

Traded Ville Leino to the Flyers for Ole-Kristian Tollefsen. Traded Andy Delmore to the Flames for Riley Armstrong. Traded Kris Newbury to the Rangers for Jordan Owens. 
Hossa left the Wings in the off-season to sign with the Blackhawks and Holland replaced him by bringing back Todd Bertuzzi as a free agent. Detroit made a few deals ahead of the trade deadline in 2009-10 but all of them were minor.
The Red Wings didn’t win their division that season for the first time since 1999-00 and they lost in the second round of the playoffs in five games to the Sharks.

The 2010-11 Red Wings

The 2010-11 season featured another quiet trade deadline for Holland. The Wings wound up losing in the second round of the playoffs to the Sharks in seven games.

The 2011-12 Red Wings

Traded Sebastian Piche and a first-round pick to the Lightning for Kyle Quincey. Traded Mike Commodore to the Lightning for a seventh-round pick. 
Brian Rafalski retired following the 2010-11 season, leaving a pretty significant hole on Detroit’s blueline. Holland tried to patch that hole ahead of the trade deadline by moving a prospect and a first-round pick to the Lightning in exchange for Kyle Quincey. Holland knew Quincey well as the Wings drafted him in 2002 but lost him on waivers before he found his footing in the NHL.
The Wings lost in the first round of the playoffs to the Predators, marking the first time they had failed to advance past the first round since their loss to the Oilers in 2006. That summer, the Lightning used Detroit’s first-round pick to select Andrei Vasilevskiy. Quincey, meanwhile, was re-signed to a two-year deal.

The 2012-13 Red Wings

The summer ahead of the 2012-13 season featured a significant loss for the Red Wings as captain and seven-time Norris Trophy-winning defenceman Nicklas Lidstrom retired.
After moving his first-round pick at the previous year’s trade deadline, Holland stood pat in 2013. The Red Wings cruised into the playoffs but lost in the second round in seven games to the Chicago Blackhawks, the eventual Stanley Cup winners.

The 2013-14 Red Wings

Traded Calle Jarnkrok, Patrick Eaves, and a third-round pick to the Predators for David Legwand. 
The 2013-14 season was when the Red Wings clearly started to decline. Their 93 points in the standings represented their lowest total for a season since 1998-99 and they got shoved aside in the first round of the playoffs in five games by the Boston Bruins.
By this point, it would have made sense for the Wings to start to rebuild their roster, but it was a priority late in owner Mike Ilitch’s life to see the team continue to extend their historic playoff streak.
Holland’s big move at the deadline that season to help push the Red Wings into the playoffs was acquiring veteran pivot David Legwand from the Predators in exchange for two prospects and a third-round pick. Calle Jarnkrok developed into a good player for the Preds while Legwand left Detroit as a free agent in the off-season.

The 2014-15 Red Wings

Traded Mattias Janmark, Mattias Backman, and a second-round pick to the Stars for Erik Cole and a third-round pick. Traded a third-round pick to the Devils for Marek Zidlicky. 
Holland again made a trade involving prospects the following season, as he moved Mattias Janmark, Mattias Backman, and a second-round pick to the Stars to acquire Erik Cole. He also traded a third-round pick to the Devils to add veteran defenceman Marek Zidlicky.
The Wings lost in the first round of the playoffs to the Lightning in seven games and both Cole and Zidlicky left the team in the off-season. Detroit also saw head coach Mike Babcock leave the team to join the Toronto Maple Leafs.

The 2015-16 Red Wings

Traded Jakub Kindl to the Panthers for a sixth-round pick. 
The Wings barely snuck into the playoffs in 2015-16 as the eighth seed in the Eastern Conference and lost in the first round to the Lightning, this time in five games. Holland’s only move this season was moving depth defender Jakub Kindl to the Panthers for a late draft pick.

The 2016-17 Red Wings

Traded Tomas Jurco to the Blackhawks for a third-round pick. Traded Brendan Smith to the Rangers for a second- and a third-round pick. Traded Thomas Vanek to the Panthers for Dylan McIlrath and a third-round pick. Traded Steve Ott to the Canadiens for a sixth-round pick. 
In the summer of 2016, Pavel Datsyuk announced his retirement from the NHL. Holland tried to replace his place in the Red Wings’ lineup by inking veteran centre Frans Nielsen to a six-year, $31.5 million contract in free agency.
By the turn of the new year, it was clear that the Red Wings weren’t going to make the playoffs. Mike Ilitch passed away in February and Holland started to move into a rebuilding phase shortly after, as Tomas Jurco, Brendan Smith, Thomas Vanek, and Steve Ott were traded for draft picks.
Detroit’s streak of consecutive seasons in which they made the playoffs ended that spring at 25.

The 2017-18 and 2018-19 Red Wings

Traded Petr Mrazek to the Flyers for a third- and a fourth-round pick. Traded Tomas Tatar to the Golden Knights for a first-, a second-, and a third-round pick. Traded Nick Jensen to the Capitals for Madison Bowey and a second-round pick. Traded Gustav Nyquist to the Sharks for a second- and a third-round pick. 
The next couple of seasons saw Holland sell off players on expiring contracts in order to stockpile draft picks. Petr Mrazek and Tomas Tatar got moved ahead of the 2018 trade deadline and Nick Jensen and Gustav Nyquist were traded away the following year.
Following the 2018-19 season, Holland was named the general manager of the Oilers, and he was replaced in Detroit by Steve Yzerman.

The 2019-20 Oilers

Traded Sam Gagner and two second-round picks to the Red Wings for Andreas Athanasiou and Ryan Kuffner. Traded Kyle Brodziak and a fourth-round pick to the Red Wings for Mike Green. Traded a fifth-round pick to the Senators for Tyler Ennis. 
The Oilers got off to a great start in Holland’s first season in Edmonton and he leaned into it by adding three players ahead of the trade deadline. Holland moved two later-round picks for veterans Tyler Ennis and Mike Green and two second-round picks to acquire Andreas Athanasiou, a player he had drafted and developed in Detroit.
The season got paused a few weeks later because of the pandemic and the Oilers wound up losing in the play-in round of the summer bubble tournament. In the off-season, Green retired, Ennis was re-signed, and Athanasiou was a casualty of a lower-than-expected salary cap ceiling.

The 2021 Oilers

Traded a fourth-round pick to the Devils for Dmitri Kulikov. 
Edmonton cruised into a playoff spot during the pandemic-shortened 2021 season in the All-Canadian Division. But after trading four draft picks the previous year, Holland was conservative at that season’s trade deadline, only moving a fourth-round pick for shutdown defender Dmitri Kulikov.
In the playoffs, the Oilers got swept by the Jets in four games. In the off-season, Holland made some significant moves, signing Zach Hyman in free agency and acquiring Duncan Keith in a trade with the Blackhawks.

The 2021-22 Oilers

Traded William Lagesson and a second-round pick to the Canadiens for Brett Kulak. Traded a fourth-round pick to the Flyers for Derick Brassard. 
The Oilers got off to a great start in 2021-22 but cratered in December and January. Adding Evander Kane as a free agent in January along with firing head coach Dave Tippett and replacing him with Jay Woodcroft in February helped turn the season around.
At the trade deadline, Holland added to the team’s depth by acquiring Brett Kulak and Derick Brassard. The Oilers proceeded to go on their longest playoff run since 2006, taking down the Kings and Flames before losing to the Avalanche in the Western Conference Final.
The following off-season was spent keeping the band together, as mid-season additions Kulak and Kane were re-signed to new contracts.

The 2022-23 Oilers

Much like last year, the 2022-23 season has been a bit of a rollercoaster ride in Edmonton, but the Oilers’ recent winning streak has them right in the conversation to win the Pacific Division. Also, with the struggles the Avs and Golden Knights have had with injuries, there’s a very clear path for the Oilers to come out of the Western Conference.
Many signs point to this being a year for the Oilers to go all-in but that hasn’t been Holland’s style throughout his career as a general manager. During the late-2000s when the Red Wings were serious contenders, Holland’s biggest in-season trades were acquiring Brad Stuart and Todd Bertuzzi, and he was completely comfortable letting the deadline pass without making a move. He’s only moved his first-round pick once and Holland never traded his top prospects in deadline deals while with the Red Wings.
With that in mind, it would be very surprising to see Holland deal players like Dylan Holloway, Philip Broberg, Xavier Bourgault, and Reid Schaefer ahead of the March 3 deadline for the Oilers to make a run this spring. The biggest swing Holland is likely to take would instead involve draft picks as the main pieces going out, with players he believes he can re-sign coming back in return.
While winning a Stanley Cup in Edmonton is his ultimate goal, it’s also certainly a priority for Holland and his legacy to leave behind a strong system when he sails into the sunset.

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