Looking back at Ken Holland’s history in free agency
By Cam Lewis
2 years agoIt’s expected that Ken Holland will be active in free agency this summer.
The Oilers have lost in the first round of the playoffs in back-to-back years, indicating that Connor McDavid and Leon Draisaitl need help to get over the hump and reach the next level.
After spending his first couple of years dealing with a difficult salary cap situation left behind by Peter Chiarelli, Holland will have plenty of room to work with this off-season. His checklist includes adding depth to Edmonton’s top-nine forward group, finding a veteran left-handed defender, and figuring out the goaltending situation.
Holland is no stranger to shopping on the free-agent market.
In his early days as general manager of the Detroit Red Wings, he was blessed with an owner in Mike Ilitch who would spend an infinite amount of money in order for the team to be competitive. Whether that was bringing in a Hall of Famer like Brett Hull, Luke Robitaille, or Dominik Hasek late in their career or going across the Iron Curtain to lure talent like Sergei Fedorov or Slava Kozlov overseas, Ilitch always gave his front office the cash to get the best.
Times obviously changed after the 2004-05 lockout. The implementation of the salary cap made it so teams like Detroit couldn’t simply go out and throw a blank cheque at whichever player they wanted. Teams had to become more strategic with how they assembled their rosters, focusing on drafting and developing talent and then going hard after game-changing free agents.
Holland’s list of major off-season signings in the salary cap era isn’t as extensive as his Hull, Robitaille, and Hasek days, but he’s still shown a willingness to sign major contracts in free agency. Here are Holland’s notable unrestricted free-agent deals in the salary cap era…
- 2006: Mikael Samuelsson, three years, $3,600,000.
- 2007: Brian Rafalski, five years, $30,000,000.
- 2008: Marian Hossa, one year, $7,450,000.
- 2008: Dan Cleary, five years, $14,000,000.
- 2008: Brad Stuart, four years, $15,000,000.
- 2013: Stephen Weiss, five years, $24,000,000.
- 2015: Brad Richards, one year, $4,000,000.
- 2016: Frans Nielsen, six years, $31,500,000.
- 2016: Mike Green, three years, $18,000,000.
- 2016: Thomas Vanek, one year, 2,600,000.
- 2017: Trevor Daley, three years, $9,500,000.
- 2018: Thomas Vanek, one year, $3,000,000.
There are a handful of very good signings from early on in the salary cap era in Detroit.
After losing to the Oilers in the first round of the 2006 playoffs, Holland inked winger Mikael Samuelsson to a dirt-cheap, one-year deal. Samuelsson had a good season in 2005-06 and Holland signed him to a three-year deal worth just $1,200,000 annually. Over those four years, Samuelsson scored 159 points in 278 games.
Another example of this bargain-bin hunting is former Oiler, Dan Cleary. Holland signed Cleary in 2005 to a cheap one-year deal, he got a two-year deal after that, and then signed a five-year deal when he became UFA eligible. Cleary put up 265 points in 540 games during those eight seasons and was a valuable depth player for the Red Wings.
Holland’s first major deal of the cap era was signing Brian Rafalski, a Michigan native, after the team lost in the Western Conference Final to the Anaheim Ducks in 2007. Rafalski was excellent for the Wings, putting up 204 points in 292 games over four seasons. He played a key role on Detroit’s 2008 Stanley Cup squad, logging 24:53 per game in the playoffs.
Another major player on that 2008 team was Brad Stuart, a rental that Holland acquired at the trade deadline. Stuart rounded out Detroit’s top-four on the blueline, logging 21:40 per game in the playoffs. Stuart was a free agent after the Stanley Cup run and Holland re-signed him to a four-year deal. He would log 21:33 per game over those four seasons and was a solid defender.
This situation illustrates Holland acquiring a rental with the goal of keeping him around. That may or may not be relevant this summer with Dmitry Kulikov.
Finally, there’s Holland’s best deal in the salary cap era — Marian Hossa. After losing to the Red Wings in 2008, Hossa left Pittsburgh as the biggest name on the free-agent market. Holland got Hossa to sign a one-year deal with the team that beat him in the Stanley Cup Final. With the Wings, Hossa put up 40 goals and 71 points. Ironically, Hossa lost to his former team, the Penguins, in the 2009 Stanley Cup Final.
Regardless, this was an excellent signing, one of the best in the salary cap era. Holland managed to get one of the league’s better forwards to gamble on a one-year deal in order to try to help push the Red Wings to back-to-back Stanley Cups.
What we have here is Holland making good signings to augment an elite core. He had Nicklas Lidstrom, Pavel Datsyuk, and Henrik Zetterberg forming the foundation of a very good team and used free-agent signings, both small and large, to push that team over the top.
In the post-Lidstrom era, though? Things weren’t quite as successful.
In 2011-12, the Red Wings lost in the first round of the playoffs to the Nashville Predators. It was their first time failing to get out of the first round since they were upset by the Oilers. Much like with Steve Yzerman in 2006, that was the end of the line for Lidstrom.
In the lockout-shortened 2013 season, the Wings went 24-16-8, their worst result in terms of points percentage since the 90s. That summer, Holland inked Stephen Weiss to a five-year deal worth $4,900,000 annually despite the fact he was coming off of a performance in which he put up four points in 17 games. Weiss was a disaster in Detroit. Over two seasons, he scored 29 points in 78 games and was bought out.
A few years later, Holland again dipped into the free-agent market in search of a quality second-line pivot. This time, it was Frans Nielsen, who had been one of the league’s better two-way centres with the New York Islanders throughout the 2010s. Nielsen had a couple of good seasons in Detroit but has completely fallen off a cliff. Over the past two seasons, Nielsen scored 15 points in 89 games with a $5,250,000 cap hit. He has one more year left on that deal.
Holland also spent major dollars to shore up the blueline during this era, signing Mike Green and Trevor Daley. Green was productive and had some solid seasons in Detroit while Daley was a competent but unspectacular veteran. Green’s $6,000,000 annual salary was a bit rich for what he provided and Holland likely could have found a shutdown guy at a cheaper price tag than Daley’s $3,166,666.
The one good signing Holland made during this time was Thomas Vanek. In 2016, Vanek inked a one-year, $2,600,000 deal and scored 38 points in 48 games before getting moved ahead of the trade deadline. Vanek was back on another one-year deal in 2018 and he scored 36 points in 68 games.
What does it all mean?
There are three distinct eras in Holland’s career as the general manager of the Detroit Red Wings.
There was the pre-salary cap era in which he could get Mike Ilitch to spend an insane amount of money for the team to bring just about anybody they wanted. There was the in-between era after the implementation of the salary cap in which Holland was able to augment a strong internally-developed core with smart free-agent additions. Finally, there was the post-Nick Lidstrom era in which Holland tried to keep a declining Red Wings team above water by overpaying for good-not-great veterans on the free-agent market.
The writing was on the walls and there was no doubt that the Red Wings should have entered a rebuilding phase shortly after Lidstrom retired. But, to be fair to Holland, Ilitch didn’t want to see the team’s historic playoff streak come to an end before he passed away and mandated that the front office do what it needed to do in order to remain competitive. The Weiss, Daley, and Neilsen signings were undoubtedly bad, but I’m willing to cut Holland come slack here.
The Oilers aren’t the late-2000s Red Wings, but, with Connor McDavid, Leon Draisaitl, and Darnell Nurse, Holland has about as good of a core as anybody to work with. Given his poor luck with big free-agent contracts in his later days in Detroit, Holland might be best using his cap room to sign a lot of mid-level players to improve Edmonton’s depth.
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