Ken Holland’s work at the trade deadline

It’s been a long, long time since the Oilers made a trade deadline splash. That could change this year.

Rolling along despite the injury to Connor McDavid, this Oilers team have earned themselves an investment from general manager Ken Holland. Beyond being just a team that squeaks into the playoffs, the Oilers truly look like they could do some damage in the wide-open Western Conference come spring.

The last time we saw an Oilers general manager really go all-in was back in 2006 when Kevin Lowe put together his banner series of work, acquiring Jaroslav Spacek, Sergei Samsonov, Dwayne Roloson, and Dick Tarnstrom. The four additions ultimately helped the Oilers come to within one win of winning the Stanley Cup that year.

Since then? There hasn’t been much, unless you fondly remember Steve Tambellini’s bold acquisition of Jerred Smithson. Even Peter Chiarelli only went out and added David Desharnais ahead of the team’s playoff run in 2017.

So, what can we expect from Holland this year? Let’s take a look back through his history at the deadline to get an idea of what might be ahead.

Holland has been a general manager in this league for over 20 years now. It isn’t necessary to go back and look at every single trade deadline he’s been a part of in detail because the league completely shifted after the 2004-05 lockout.

Before that, he could operate the Red Wings with virtually unlimited financial flexibility. After the salary cap was introduced, teams had to be much more conservative with how they spent money and the ensuing domino effect led to an increased value being attached to drafting and developing players internally. As a result, the trade deadline is much different now than it was twenty years ago.

Instead of going deadline by deadline here, I’ll just talk about some of the interesting moves Holland made before the implementation of the salary cap.

In 1999, just his second-ever deadline as general manager of the Wings, Holland sent Anders Eriksson and two first-round picks to Chicago in exchange for former Norris Trophy winner Chris Chelios. The team was seeking a Stanley Cup three-peat, so Holland also acquired veterans Wendel Clark and Bill Ranford, though they ended up losing in the second round to the Colorado Avalanche. Still, the ageless wonder Chelios went on to be a great defenceman with the Wings for the next decade, helping the team win the Cup in 2002 and 2008.

The next few deadlines were quiet in Detroit, including the one ahead of the team’s Stanley Cup win in 2002. Holland’s next deadline splash would come in 2003 when he sent Sean Avery and a first- and second-round pick to Los Angeles for offensive defenceman Mathieu Schneider. The Wings would suffer a shocking sweep by the Mighty Ducks that spring. The following year, Holland sent Thomas Fleischmann and a first-round pick to Washington in exchange for Robert Lang. The Wings would yet again be shocked by a low seed in the playoffs that year, this time by the Flames.

While neither 2003 or 2004’s acquisitions resulted in deep playoff runs, both Schneider and Lang stuck around and put up productive seasons with the Wings for a few years after. When you put Chelios into consideration, all of Holland’s big pre-lockout deadline splashes were more than just rentals.

Here we are now, in the salary cap world. With the Wings pressed right up to the ceiling, Holland had a pretty stagnant deadline. Detroit cruised to a Presidents’ Trophy win in 2005-06, acquiring only depth players Cory Cross (who had a few weeks earlier been sent to the Penguins along with Jani Rita for Dick Tarnstrom) and Jamie Rivers. We all know what happened to the Wings in the playoffs that year.

The following year, looking to avenge their upset in the first round at the hands of the Oilers, Holland had a much more exciting trade deadline. He sent Jason Williams to Chicago in a hockey deal for Kyle Calder, but the big splash was acquiring the controversial Todd Bertuzzi from Florida in exchange for Shawn Matthias and a second-round pick. There was also another second-rounder in the deal contingent on Bertuzzi re-signing in Detroit, but he left in free agency, though he did return to Detroit again later in his career.

Bertuzzi would post four points in eight games for the Wings down the stretch and seven points in 16 playoff games, helping Detroit reach the Western Conference Final before they got taken down by the Ducks, the eventual Cup winners.

The 2008 trade deadline only featured one move by Holland, but it was an important one. Holland sent a second- and a fourth-round pick to L.A. for veteran defenceman Brad Stuart who helped round out the team’s top-four. Stuart played 21:40 per game in the playoffs for the Wings, helping the Wings ultimately beat the Penguins in the Stanley Cup Final. Holland didn’t make any moves the following year as his big splash came with the off-season signing of Marian Hossa. The Wings would end up losing to the Penguins in the Final.

The 2011 and 2012 deadline didn’t produce anything of note, so we’ll skip ahead to 2013. By this point, the Wings have begun their slow decline from one of the greatest dynasties in NHL history to just another team. The lockout-shortened 2013 season represented their first without Nicklas Lidstrom and the team didn’t look like a true contender.

With some risk of their playoff streak coming to an end, Holland dealt a first-round pick to the Lightning in exchange for Kyle Quincey to help solidify the team’s blueline. Quincey was originally a fourth-round pick of the Wings back in 2002 but he didn’t establish himself in the league until he was claimed off of waivers by the Kings a few years later. He would be an unspectacular defenceman for the Wings for parts of five seasons while the Lightning used their pick on Andrei Vasilevskiy.

In 2014, Holland did something out of character by acquiring a rental. He sent Calle Jarnkrok, Patrick Eaves, and a second-round pick to the Nashville Predators for David Legwand. Again in 2015 Holland would go the rental route, this time acquiring Erik Cole and a third-round pick from Dallas for Mattias Janmark, Mattias Backman, and a second-round pick. Neither player could help the Wings in the playoffs (to be fair to Cole, he got injured) as the team lost in the first round both years.

The 2014 and 2015 deadlines were mostly about Holland pushing to keep the Red Wings’ playoff streak alive by the wish of Mike Ilitch in his final years. By that point, the Wings were far from a Cup contender and selling in order to start a rebuild would have made a lot more sense.

Holland did finally sell at the 2017 deadline shortly after the passing of Ilitch. He dealt away Brendan Smith, Tomas Jurco, Steve Ott, and Thomas Vanek before the team ultimately missed the playoffs for the first time in 25 years. That would be Holland’s mantra in 2018 and 2019 as well, as he dealt away Tomas Tatar and Gustav Nyquist in order to stockpile draft picks for the team’s rebuild.

As I said earlier, Ken Holland has been a general manager for a really long time so there’s a lot to take in when analyzing his work at the trade deadline.

It’s also pretty difficult to compare Holland in the past to Holland now because the context has changed so much. His years before the lockout operating without a salary cap are completely different than the situation he’s in now. Also, his later years in Detroit saw him walking the tightrope of trying to keep alive a legendary playoff streak for a dying owner.

What we can draw from Holland’s history, though, is that he isn’t afraid to make a move, but he’ll very likely be looking for players who can help beyond this season and he’ll try to avoid using his first-round pick.

Looking back through his deals, only once in the post-lockout era did Holland deal away a first-round pick to acquire a player. That was the Quincey deal in which he gave Tampa Bay a first-rounder in order to add a top-four defenceman he seemed to believe could be a part of the solution long-term. Quincey was a restricted free agent the summer after he was acquired and Holland inked him to a two-year deal. Tampa Bay ending up with Vasilevskiy out of this looks bad, but is more simply impressive work on the part of the Lightning than it is a failure by Holland.

Otherwise, all the other players Holland acquired at the deadline were done so with later picks. Whether it was Bertuzzi, Legwand, or Stuart, Holland avoided using his first-round pick in order to augment his team at the deadline. These players also weren’t the big names of their respective deadlines. It seems Holland has settled for more veteran depth upgrades rather than going big game hunting because he wants to avoid giving up his top draft pick.

So, with all that in mind, we have a pretty good idea of what to expect from Holland in the next few days. We almost certainly won’t see the first-round pick moved unless the player coming back has term or control beyond this season and we’ll likely see Holland go for veteran depth rather than star-calibre names.