In part seven of our look at the Western Conference GMs, we will look at future Hall of Famer Ken Holland who was the GM of the Detroit Red Wings for almost 22 years, the assistant GM before that for three years and the director of amateur scouting for seven years before that. He has been the GM in Edmonton for just over one year now.

Other than team records, we will only look back beginning with the 2009-10 season for Holland for trades, drafting and signings as I don't wish to write a novel.

Rating:

5: below average

6: average

7: above average

8: top ten

9: Exceptional

10: Perfect

Prior Ratings:

Bob Murray – Anaheim: 7.85

John Chayka – Arizona: 6.62

Brad Treliving – Calgary: 7.5

Stan Bowman – Chicago: 7.6

Joe Sakic – Colorado: 7.55

Jim Nill – Dallas: 7.225

Edmonton Oilers

GM – Ken Holland, hired May 7^th, 2019

First category, winning:

Regular season record with Edmonton: 37W 25 L 7 OTL 2 SOL: 0.585 Win %

Regular season record with Detroit: 925 W 523 L 72 Ties 97 OTL 71 SOL: 0.618 Win %

Holland's winning percentage for the first ten years compared to the last ten years of his time as GM: 0.671 Win % from 1997-98 through 2008-2009 and 0.558 from 2009-10 through 2018-19.

Playoffs: The Red Wings won the Stanley Cup three times in 1997-98, 2001-02 and 2007-08, and lost in the Finals in 2008-09. Detroit missed the playoffs the last three seasons that Holland was there. With Edmonton this past season, the team would be the 5^th seed if the playoffs continue in the rumored 24-team format floating around.

Best result: Holland's best regular season was in 2005-06 when the Red Wings won 58 games and posted 124 points, but were bounced in the first round of the playoffs.

Holland was named the GM in Edmonton after the end of the 2018-19 season. He inherited a great young nucleus in Connor McDavid (21), Leon Draisaitl (22), Ryan Nugent-Hopkins (25), Darnell Nurse (23), and Oscar Klefbom (25). The prospect pool consisted of Kailer Yamamoto, Jesse Puljujarvi, Caleb Jones, Evan Bouchard, Tyler Benson, and Ethan Bear.

He hired Dave Tippett as head coach three weeks after being hired himself.

Winning rating: 7.2 (post-2009); 9.2 (pre-2009)

Drafting:

Since the 2009-10 season, Holland has drafted 88 players, with six of those in the 2019 draft for Edmonton. With Detroit being such a good team, most of the 1^st round picks Holland would have were in the bottom half of the round until more recently. The 9^th overall pick in 2017 (Michael Rasmussen), the 6^th overall pick in 2018 (Filip Zadina) and the 8^th overall pick in 2019 (Philip Broberg) have been the past three drafts for Holland.

Other than 2010 and 2014, drafting under Holland has been slightly below the NHL standard. Notable picks that were successful for the scouting staff and management were Riley Sheahan at 21^st overall, Calle Jarnkrok at 51^st overall and Petr Mrazek at 141^st overall in 2010. Andreas Athanasiou would have to be considered a good pick at 110^th overall in 2012 along with Anthony Mantha at 20^th overall and Tyler Bertuzzi at 58^th overall in 2013. Dylan Larkin at 15^th overall in 2014 and Filip Hronek at 53^rd overall in 2016 are the latest likely successes.

Holland and his staff have not had very many misses, but Evgeny Svechnikov at 19^th overall in 2015 is trending that direction after battling injury and missing all of 2018-19 (he did see four games this past season in Detroit), so perhaps the jury is still out on him, along with  Dennis Cholowski, Michael Rasmussen, Filip Zadina and Joe Veleno.

Prospects added by Holland in Edmonton in the 2019 draft are Broberg, Raphael Lavoie and goalie Ilya Konovalov, who all have fairly high upside.

Drafting score: 6.9 (post 2009)

Trading:

Trades made (post 2009): 39

Significant trades:

June 26^th, 2009 – sent a 1^st round 29^th overall pick in 2009 (Carter Ashton) for a 2^nd round 32^nd overall pick (Landon Ferraro) and a 3^rd round 75^th overall pick (Andrej Nestrasil) in 2009. Once again, we see the overpayment from a team willing to move up three spots in the draft and give up a 3^rd round draft pick. A good trade by Holland.

June 24^th, 2011 – sent a 1^st round pick 24^th overall pick in 2011 (Matt Puempel) for a 2^nd round #35^th overall (Tomas Jurco) and a 2^nd round 48^th overall pick in 2011 (Xavier Ouellet). Detroit moved down 11 spots and added a 2^nd round pick. A good formula.

February 21^st, 2012 – sent a 1^st round 19^th overall pick in 2012 (Andrei Vasilevskiy) for Kyle Quincey. Quincey was solid for Detroit, but was never going to be the top-four defenseman that should warrant a 1^st round draft pick in return. It hurts even more that Tampa Bay picked Vasilevskiy.

June 30^th, 2013 – sent a 1^st round 18^th overall pick in 2013 (Mirco Mueller) for a 1^st round 20^th overall pick in 2013 (Anthony Mantha) and a 2^nd round 58^th overall pick in 2013 (Tyler Bertuzzi). Had no other GM figured out the strategy of trading up two or three spots doesn't usually work with Holland and he was going to take advantage? Three years in a row for Holland. Quite a trade.

March 5^th, 2014 – sent Patrick Eaves, Calle Jarnkrok and a 2^nd round 46^th overall pick in 2014 (Julius Bergman) for David Legwand. A rental acquisition in Legwand, who was fading at the age of 33 when added. Detroit was bounced in the first round and gave up far too much in return.

June 28^th, 2014 – sent a 3^rd round 76^th overall pick in 2014 (Elvis Merzlikins) and a 3^rd round 80^th overall pick in 2015 (Brent Gates) for a 3^rd round 63^rd overall pick in 2014 (Dominic Turgeon). Holland's own strategy was used against him.

March 1^st, 2015 – sent Mattias Backman, Mattias Janmark and a 2^nd round 49^th overall pick in 2015 (Roope Hintz) for Erik Cole and a 3^rd round 73^rd overall pick in 2015 (Vili Saarijarvi). I think Cole was held together by tape at this point in his career, so it was pretty large overpayment at the time and in hindsight.

June 24^th, 2016 – sent Pavel Datsyuk and a 1^st round 16^th overall pick in 2016 (Jakob Chychrun) for Joe Vitale, a 1^st round pick 20^th overall in 2016 (Dennis Cholowski) and a 2^nd round 53^rd overall pick in 2016 (Filip Hronek). Once again, Holland went back to his strengths of moving down four spots to get two good picks. Datsyuk was never going to play and Arizona needed to reach the cap floor. A good trade for Holland after being in a bit of a slump.

February 28^th, 2017 – sent Brendan Smith for a 2^nd round 33^rd overall pick in 2018 (Jonatan Berggren) and a 3^rd round 83^rd overall pick in 2017 (Zachary Gallant). Brendan Smith was an expendable 6^th defenseman on the Red Wings at the time and Holland got very good value in return.

February 19^th, 2018 – sent Petr Mrazek for a 2^nd round 72^nd overall pick in 2019 (Ronnie Attard) and a 3^rd round 81^st overall pick in 2018 (Seth Barton). Mrazek was an impeding UFA and not in the plans of Detroit going forward. They received fairly good value in return.

February 26^th, 2018 – sent Tomas Tatar for a 1^st round 30^th overall pick in 2018 (Joseph Veleno) and a 2^nd round 54^th overall pick in 2019 (Robert Mastrosimone) and a 3^rd round pick in 2021. Tatar has gone on to become a top-line player in Montreal, but it was evident it was not going to happen while with Detroit. Veleno might be the diamond in this deal.

February 25^th, 2019 – sent Gustav Nyquist for a 2^nd round 60^th overall pick in 2019 (Albert Johansson) and a 3^rd round pick in 2020. It is amazing to see the decline in rental prices for a player like Nyquist when returns for similar players would have easily gathered a 1^st round pick plus in return in prior years.

July 19^th, 2019 – sent Milan Lucic and a 3^rd round pick in 2020 for James Neal. The 3^rd round pick is contingent on Neal scoring 21 goals and he got stuck on 19 before the season was suspended. It will be interesting how some of these conditions play out with the suspension in play.

July 26^th, 2019 – sent John Marino for a 6^th round pick in 2021. Not only did most people not see Marino's rookie season coming but clearly Holland did not see him playing in the NHL. What a gift to the Penguins for very little.

February 24^th, 2020 – sent Sam Gagner, a 2^nd round pick in 2020 and a 2^nd round pick in 2021 for Andreas Athanasiou and Ryan Kuffner. Holland knows Athanasiou very well and is wagering on the fact that if you can score 30 goals in Detroit on a middling team, what could he possibly do on a line with McDavid or Draisaitl? Early returns were not that great, but this trade is still open for discussion.

Trade score: 7.9 (post 2009)

Signings:

I enjoy writing these pieces on the GMs because, usually I don't really have a pre-conceived notion of how well or how badly each GM has done in each of these categories. With Holland, I must admit that I've been thinking for years that he was one of the worst GMs in the past ten years for giving out bad contracts.

In over 22 years, Holland has signed 266 players to contracts for a value exceeding $1.236 billion. When the Red Wings were winning he made some very good signings to keep the roster intact, but the demand for more money grows as players win and eventually in a salary cap world it becomes unsustainable.

Holland has bought out four players in Detroit, Carlo Colaiacovo, Jordin Tootoo, Stephen Weiss and Xavier Ouellet along with Andrej Sekera in Edmonton which was not his signing. The worst of these by far is the five year deal given to Weiss at an AAV of $4.9 million. Weiss was bought out after battling injuries and inconsistencies (and Mike Babcock) over two seasons and ended up retiring from the NHL.

Edmonton has just over $12 million in cap space for next season (assuming the salary cap stays the same) and will need to re-sign Athanasiou, Matthew Benning, and Ethan Bear and sign a backup goalie, but Holland should be able to easily come in under the cap, unless he goes spending on July 1^st, or whenever the free agency date is. Most of his signings so far in Edmonton have been short-term or low money and the only deal that might be of concern in a year or two is Zack Kassian at $3.2 million AAV until the end of 2023-24.

It was his time in Detroit that Holland set the bar for bad contracts:

Frans Nielsen signed for six years at $5.25 million AAV.

Jimmy Howard signed for six years at $5.29 million AAV.

Danny DeKeyser signed for six years at $5 million AAV.

Stephen Weiss signed for five years at $4.9 million AAV.

Justin Abdelkader signed for seven years at $4.25 million AAV.

Jonathan Ericsson signed for six years at $4.25 million AAV.

Darren Helm signed for five years at $3.85 million AAV.

Trevor Daley signed for three years at $3.167 million AAV.

All of these deals are still on the payroll and are mostly dead weight in terms of cap space. Holland did not do Detroit any favors in the past five seasons.

He has been patient so far in Edmonton, but the upcoming free agency will be the true test for him to see if he can avoid starting an Edmonton list like the one above, he left Detroit.

Signings score: 5.7

Overall score 6.925 (post 2009)

I don't think there is any doubt Holland will be in the Hockey Hall of Fame and he might be above nine for his work with the Red Wings pre-2008, but we are focusing on his past ten or eleven seasons for the most part.

I think if you asked anyone who they would like to build their franchise around, 99% would say Connor McDavid. Holland has been put in charge of a young team who should be very competitive from this season and for the next six or seven if Holland does anything close to the job he has done before in Detroit.

As always, thanks very much for reading and if you have any comments or suggestion please let me know below or follow me on Twitter @gampbler15.