With rumours abound, the intrigue surrounding the Edmonton Oilers approach to the early March trade deadline is in full bloom. The Oilers are rounding into form, looking far more like the team of last spring than this fall’s performance. The Western Conference and Pacific Division are both wide open. The Oilers have virtually no cap space to add, but the team does have the willingness and resources to be in on all the biggest names.
With that said, all eyes are on Oilers GM Ken Holland. How aggressively will futures be moved? What positions will or won’t be prioritised? With the answer to when any deals might be made drawing near, this precipice is a time to wonder what those might be. Though following insiders up to the minute may offer some speculations, it is perhaps Holland’s extensive history that might best inform the future. Without further ado let’s analyse Holland’s deadline history and how it might be relevant to this year’s Oilers.
Holland managed the Red Wings before the cap era
For the purposes of this (brief) exercise it is not overly important to analyse Holland’s pre-cap deadline work. The Detroit Red Wings of the early 2000s were a dynasty that spent among the highest of any team in the league. The Wings were one of the few teams that had to drastically cut salary to get underneath the initial NHL salary cap.
In such a world, draft picks were far less important, as teams could buy to the content of their owner. Players were not necessarily as more or less impactful based on their salaries. The Wings took advantage, often with depth and name brand recognition that has scarcely been seen since.
Detroit was a true cap era contender
Out of the 2004–05 lockout, the Red Wings were still a top tier team. With an abundance of talent, living legend Hall of Famers, recent Cup wins, and ultimately what would result in the longest streak of consecutive playoff appearances across any of the four major North American sport leagues.
While the Oilers are still proving their mettle as the perennial contenders, this war might be the most instructive of how Holland might operate.
In 2006, Cory Cross was traded for a 2007 fourth-round pick: 118th overall, Alex Grant. Holland acquired a bottom pair defender for a low pick. The 2005–06 Red Wings dominated the regular season, winning the Presidents Trophy. The playoffs held a different story, with the Wings being upset by the eighth seed Oilers. To this day this is one of the prime examples of the Presidents Trophy curse.
The next year, Holland traded Kyle Calder for Jason Williams, and Todd Bertuzzi for Shawn Matthias, and a 2007 second-round pick, Nick Spalding. The Wings had a decent run, advancing to the Western Conference Final but falling to the eventual champions, the Anaheim Ducks.
The biggest move of the 2007–08 season came in the summer, signing Brian Rafalski, though at the deadline Holland added to the blueline again, getting Brad Stuart for a pair of mid-round picks. Both Stuart and Rafalski played huge minutes on the blueline as the Wings won the Cup.
The next summer once again had the biggest move, adding Marian Hossa as a free agent. No deals were made at the deadline and the Wings lost in the 2009 Stanley Cup Finals.
A busier deadline, Holland did not exactly buy at the 2009–10 deadline. The biggest move here was trading out Ville Leino, who was fighting for a regular lineup spot. Leino would be an amazing player later for a short time.
The Red Wings slowly aging out
The Wings dynasty was starting to fade from this point, with many of their best players beginning to retire. Despite this, Holland made no moves in the 2010–2011 season.
In a relatively big move for Holland’s record, Kyle Quincy was brought in as a top four puck mover for a first and a prospect. Naturally the player that became of the first-round pick is notable, but that shouldn’t necessarily impact how we view the deal. A team on the decline, it’s fair to think that Holland may have overextended himself slightly. The Red Wings lost in the first round of playoffs in 2012.
Despite making no deadline deals the following year, the Wings made it to the second round. Perhaps Holland saw the team’s inevitable decline on the horizon.
Owner Ilitch’s push for success
Though some of the Wings legendary players were still in the lineup, by this point the team was obviously out of its contending status, yet for one reason or another Holland was at his most aggressive. Some say it might’ve been in an effort to keep the Wings playoff streak going, or perhaps a push to stay as competitive as possible in owner Mike Ilitch’s advancing age. Grabbing a middle six centre for a player, a pick, and a prospect is a fairly significant move. Despite the upgrade the Wings lost in the first round in 2014–2015.
A scoring forward for two prospects and a puck swap, Erik Cole was injured shortly after the trade and never got to work out for the Wings. A veteran puck moving defenceman, Marek Zidlicky was added for a mid-round pick. The additions did little to help the Wings in the playoffs in 2015.
Perhaps it was at this point that Holland realised the Wings window was firmly shut., holding on for one last playoff appearance the next year.
Ilitch passes, sell starts
Whether it was a new vision from ownership or the Wings reality as a likely rebuild, 2016–17 marked the end of the Wings playoff streak and a new era for the club.
In 2017, Holland made moves that were all selling veteran players for mid-round picks, showing that buying or selling Holland is comfortable operating at this price.
Holland did quite well in selling a few assets in 2018, though accumulating draft picks doesn’t always yield players. The playoffs were missed once again.
Holland signed on with the Oilers in May of 2019
The 2019–20 deadline is a complicated deadline to evaluate, given the world shut down. The Oilers did poorly in the resumed bubble. Though mid-round picks are frequently a part of Holland’s trades, two second rounders is one of the bigger buys across Holland’s career. Mike Green was acquired for Kyle Brodziak and late picks.
Brock Faber and Aatu Raty, players selected in the second round have been parts of notable trades since, Kevin Fiala to the Los Angeles Kings, and Bo Horvat to the New York Islanders. It is hard to feel like these deals paid off, though that might have to do with the team’s loss in the play-in round or that none re-signed.
Another complicated deadline in 2021, with the short lived North Division requiring a two week quarantine prior to joining a lineup. The Oilers did not have enough, ultimately losing to the Winnipeg Jets, though it is difficult to fault Holland for not being more aggressive here.
Last season’s trade deadline might have been the most ambitious yet, in part thanks to the strange circumstances that led to Evander Kane becoming available. Derrick Brassard for a fourth-rounder is a classic Holland deadline move, while the Brett Kulak move is reminiscent perhaps of the Brad Stuart deal in 2008. The Oilers eventually lost in the WCF to the would-be Stanley Cup Champions, the Colorado Avalanche.
Predictions for the 2023 deadline
What does this track record tell us about what to expect? At first glance a veteran forward for a mid to late pick seems likely, Nick Bjugstad perhaps? It is fair to observe that most of his best work has come in acquiring defencemen.
Holland has been involved in bigger moves as a seller than a buyer, clearly demonstrating that he values futures. Clearly Holland tries not to overextend himself in desperation at the deadline, often standing pat even with an ageing team.
Acquiring Erik Karlsson or Jakob Chychrun would likely be the biggest deadline move of Holland’s career. While not impossible, it does show that expectations might need to be tempered for bloodthirsty Oilers fans. It would, however, be a bit of a surprise not to see any moves, despite the meagre cap margins.