Ken Holland’s best and worst moves in the salary cap era

Edmonton Oilers new general manager Ken Holland joined Prime Time Sports to discuss leaving Detroit and his plans for the team.

“You’ve got to make more good decisions than bad decisions. And I think I made more good decisions in Detroit than bad decisions.”

That was Ken Holland’s message when the Edmonton Oilers introduced him as their new general manager and president of hockey operations on Tuesday.

His point? That no one is perfect, but he believes he has a good enough track record to lead the Oilers through their latest rebuild.

The 63-year-old comes to Edmonton having served as GM of the Detroit Red Wings for 22 years. That gives us lots of moves (good and bad) to analyze as a way to paint a picture of the approach Holland will take with the Oilers.

Over the years, Holland has shown a strong ability to rebuild his team without high draft picks, but has also handed contracts out for loyalty that have come back to haunt him.

For this exercise, we’ll only look back at his moves after the salary cap was introduced. Drafting Henrik Zetterberg in the seventh-round or signing Brett Hull and Luc Robitaille as free agents in the same off-season don’t really apply to his current task in Edmonton.

With that being said, here are Holland’s best and worst trades, signings and draft picks from his final 14 seasons managing the Red Wings.

Best Trades

Feb. 26, 2018: Detroit trades forward Tomas Tatar to the Vegas Golden Knights for a first-round pick (Joe Veleno), second-round pick (2019) and third-round pick (2021).

Holland hit a buzzer beater in 2018, dealing Tatar to the Golden Knights with only minutes to spare before the trade deadline. In return, he acquired three high draft picks for his rebuilding club, and while two of them have yet to be used, the first-rounder became centre Joe Veleno, who was a finalist for the QMJHL’s MVP award after scoring 42 goals and 104 points in 59 games with the Drummondville Voltigeurs this season.

June 24, 2016: Detroit trades forward Pavel Datsyuk and a first-round pick (Jakob Chychrun) to the Arizona Coyotes for forward Joe Vitale, a first-round pick (Dennis Cholowski) and a second-round pick (Filip Hronek).

After 14 seasons with the Red Wings, future Hall-of-Famer Pavel Datsyuk announced after the 2015-16 season that he would be returning to his native Russia to finish his career in the KHL. Less than a week later, Holland traded the final year of Datsyuk’s $7.5 million contract to the Coyotes and acquired two high-draft picks in return. Cholowski and Hronek, both defencemen, are key pieces in the Red Wings’ rebuild and saw ice time in the NHL this season. Chychrun made the Coyotes immediately after he was drafted, but has been limited to only 103 games over the past two seasons due to various injuries.

Livestream every game of the Stanley Cup Playoffs, blackout-free. Plus stream the Blue Jays & MLB, Raptors and NBA Playoffs matchups and more.

Worst Trades

Feb. 21, 2012: Detroit trades defenceman Sebastien Piche and a first-round pick (Andrei Vasilevskiy) to Tampa Bay; Tampa Bay trades forward Steve Downie to Colorado; Colorado trades defenceman Kyle Quincey to Detroit.

At the 2012 trade deadline, Holland reacquired Quincey (who he drafted in 2003) to shore up his defence for a playoff push. Unfortunately, to do that, he traded away the draft pick that became two-time Vezina finalist Andrei Vasilevskiy. The GM that fleeced Holland in this one? Steve Yzerman, Holland’s protégé who has now taken over for him in Detroit. The student becomes the master, one could say.

March 1, 2015: Detroit trades defenceman Mattias Backman, forward Mattias Janmark and a second-round pick (Roope Hintz) to the Dallas Stars for Erik Cole and a third-round pick (Vili Saarijarvi).

At the 2015 NHL trade deadline, in an effort to extend his team’s historic playoff streak to 24 seasons, Holland traded for veteran forward Erik Cole from the Dallas Stars. Unfortunately for Holland, Cole suffered a career-ending spine injury after only 11 games with the Red Wings. While injuries are unpredictable, the Red Wings probably wish they had a speedy forward like Hintz in their lineup now.

Best Signings

July 2, 2008: Detroit signs free agent forward Marian Hossa to a one-year, $7.45 million contract.

Less than one month after beating the Pittsburgh Penguins to win the Stanley Cup, Holland poached free agent Marian Hossa from the Penguins with a one-year contract. Hossa registered 40 goals and 71 points in his season with the Red Wings, then another six goals and 15 points in 23 playoff games. The Red Wings lost in Game 7 of the Stanley Cup Final that season in a rematch with the Penguins, and Hossa played a big part in that run.

July 1, 2007: Detroit signs free agent defenceman Brian Rafalski to a five-year, $30 million contract.

Holland made a big splash in free agency in 2007, signing right-handed defenceman Brian Rafalski away from the Devils. Rafalski helped the Red Wings win the Stanley Cup in his first season, paired mostly with Nicklas Lidstrom. In four seasons with the Red Wings Rafalski twice hit double-digits in goals, picked up 204 points and registered a plus-78. Back and knee injuries forced Rafalski to retire in 2011 before he could play the final year of his contract.

A weekly deep dive into the biggest hockey news in the world with hosts Elliotte Friedman and Jeff Marek. New episodes every Thursday.

Worst Signings

July 5, 2013: Detroit signs free agent forward Stephen Weiss to a five-year, $24.5 million contract.

Holland has a history of taking big swings at players past their prime in free agency. Mike Modano, Daniel Alfredsson, Trevor Daley and Frans Nielsen are some examples, but the 2013 signing of Stephen Weiss might be the worst one and the team is still paying for that mistake. Weiss had just turned 30 when Holland signed him, and had four 20-goal seasons with the Florida Panthers to his name. But he only scored 11 more over three injury-plagued seasons with the Red Wings. In 2015, Holland bought out the final two seasons of Weiss’s contract, and the Red Wings have a $1.67 million hit on their cap until 2021 because of it.

Nov. 12, 2015: Detroit signs forward Justin Abdelkader to a seven-year, $29.75 million contract extension.

Holland rewards loyalty, which works fine if the players are Nick Lidstrom, Henrik Zetterberg or Pavel Datsyuk. Justin Abdelkader is a different story. In the fall of 2015, a 28-year-old Abdelkader was coming off a 23 goal season and was a key winger in all aspects of the game for the Red Wings. Little did Holland know, the 2014-15 campaign would be Abdelkader’s peak. His steady decline hit a new low this season, as the now 32-year-old registered just six goals and 19 points in 71 games. The Red Wings still have him on the books with a $4.25 million cap hit (and no-trade clause) for four more seasons, which might explain why Helene St. James of the Detroit Free Press suggested the team put him on waivers if his struggles continue next season.

Best Draft Picks

2013 NHL Draft: Detroit selects forward Anthony Mantha with pick No. 20 and forward Tyler Bertuzzi with pick No. 58.

This could also fall under one of Holland’s best trades. At the 2013 NHL Draft, Holland traded pick No. 18 to San Jose for picks 20 and 58. He then used those picks to take two players who are now key to the Red Wings’ rebuild. Mantha has 49 goals and 98 points in the last two seasons combined, while Bertuzzi scored 21 goals and 47 points this season, his first full campaign in the NHL. The Sharks took defenceman Mirco Mueller with pick No. 18 and traded him to the New Jersey Devils in 2017.

2012 NHL Draft: Detroit selects forward Andreas Athanasiou with pick No. 110.

Holland has always been able to find hidden gems in later rounds of the draft and grabbing Athanasiou in the fourth-round is just one example. The 24-year-old has seen his point totals rise in each of the last three seasons, and this year he hit 30 goals for the first time, while also moving from the wing to centre. As the Red Wings continue their rebuild, the speedy Athanasiou will be a key piece of their forward group.

Ryan Dixon and Rory Boylen go deep on pucks with a mix of facts and fun, leaning on a varied group of hockey voices to give their take on the country’s most beloved game.

Worst Draft Picks

2010 NHL Draft: Detroit selects forward Riley Sheahan with pick No. 21.

In 2010, Holland had his highest pick in the first-round in five years and he used it on centre Riley Sheahan out of the University of Notre Dame. While Sheahan has been a regular in the NHL since 2013, he’s mostly been a fourth-line player and has never scored more than 14 goals in a season. He also famously almost went a whole season without a goal in 2016-17, scoring two in Game 82 to avoid that embarrassing milestone. In October of 2017, Holland traded Sheahan to the Penguins, who have since traded him to the Panthers.

2008 NHL Draft: Detroit selects goaltender Thomas McCollum with pick No. 30.

Drafting goalies is always unpredictable, but Holland whiffed badly by taking one with his first-round pick in 2008. McCollum put together a solid career in the OHL, but he’s only appeared in three NHL games and none since January of 2015. Last season, with Nashville’s AHL affiliate in Milwaukee, he had a 12-10-10 record with a 2.72 goals-against average and .899 save percentage.

When submitting content, please abide by our submission guidelines, and avoid posting profanity, personal attacks or harassment. Should you violate our submissions guidelines, we reserve the right to remove your comments and block your account. Sportsnet reserves the right to close a story’s comment section at any time.