Ken Holland was the main voice guiding the Detroit Red Wings’ player personnel decisions since he took over as general manager in 1997 following their Stanley Cup championship. Along with a braintrust that included former general manager Jim Devellano, former Red Wings players, and coach Jeff Blashill, Holland constructed a solid Red Wings roster.

In this edition of The Grind Line, The Hockey Writers’ Red Wings columnists make their picks for the best and worst Red Wings trades of the Holland era.

Note: Have champagne ready for the fantastic blockbusters and Alka Seltzer accessible for the nearsighted duds.

Tony Wolak

Best Red Wings Trade Detroit trades: Not Pavel Datsyuk ↔ New Jersey trades: Not Scott Gomez

In a 2015 article for ESPN’s Grantland, Sean McIndoe—better known as Down Goes Brown on Twitter—detailed an almost there Detroit Red Wings trade with the New Jersey Devils.

Following the 2006-07 season, the Red Wings were having trouble signing their soon-to-be unrestricted free agent Datsyuk and considered moving his rights.

Rather than risk losing Datsyuk for nothing in the summer, the Wings considered moving him for another pending free agent they thought they’d have a better shot at signing: New Jersey’s Scott Gomez.

Yikes.

Scott Gomez. (Ed Mulholland-USA TODAY Sports)

Holland almost made a terrible move, but ultimately made a great decision. Apart from winning the Stanley Cup the very next season and reaching the finals again the year after, Datsyuk had a much better next few years.

Pavel Datsyuk and Scott Gomez Point Totals

Player 2007-08 2008-09 2009-10 2010-11 2011-12 Datsyuk 97 97 70 59 67 Gomez 70 58 59 38 11

Now that Datsyuk has retired from the Red Wings and we’ve seen Gomez’s career play out, it’s a no-brainer that Holland made the right call here.

Worst Red Wings Trade Detroit trades: Sebastian Piche 1st Round Pick ↔ Colorado trades: Kyle Quincey

In a 2012 three-way deal with Colorado and Tampa Bay, the Red Wings came away with Kyle Quincey in exchange for minor league defenseman Sebastian Piche and a first-round pick. In what would become Nicklas Lidstrom and Tomas Holmstrom’s final season, Holland attempted to bolster the Red Wings’ roster as the playoffs approached.

Kyle Quincey (Photo Credit: Andy Martin Jr)

Though he had a few decent seasons with the Red Wings, Quincey wasn’t worth a first round pick, especially when you consider that he was a rental at the time. Adding insult to injury, that first-round pick turned into Andrei Vasilevskiy.

If Detroit had won the Cup that season, this deal probably would not have had the same reaction. But the fact is that the Red Wings quickly lost in the first round to Nashville, giving Tampa Bay the 19th overall selection.

Quincey was not a major factor for the Red Wings. He played on the third pairing with Jonathan Ericsson and managed two assists in the five-game playoff series against Nashville. If the Red Wings had held onto the pick, they could have selected Vasilevskiy, Brady Skjei, Olli Maatta, or Mike Matheson in the 2012 first round.

Craig Peterson

Best Red Wings Trade Detroit trades: Pavel Datsyuk’s contract 2016 16th overall pick ↔ Arizona trades: Joe Vitale 2016 20th overall pick 2016 53rd overall pick

His most recent trade may be one of Holland’s biggest trades during his time in Detroit. Nobody expected Holland to unload Pavel Datsyuk’s $7.5 million cap hit for the 2016-17 season. At times, I’m not sure Holland thought he could either, admitting at one point that he’d be willing to eat the dead money to avoid giving up prospects in the process.

Prior to the 2016 NHL Draft, Holland executed a trade that would send Datsyuk’s cap hit to the Arizona Coyotes and in return, the Wings received rights to Joe Vitale. Also in the deal, the Wings and Coyotes swapped first-round picks—Detroit moving from No. 16 overall down to No. 20 overall—and Holland squeezed out a second-round pick to conclude the deal.

Pavel Datsyuk (Photo Credit: Andy Martin Jr)

The significance of the agreement was enormous. It allowed Holland the luxury to be active in free agency. What he did with that cap space can be scrutinized and his decisions in the free-agent market have yet to pan out, but it afforded Holland the opportunity to add to the Wings roster. The deal also didn’t force him to surrender any prospects.

The trade was something that nobody expected Holland to pull off, and not only did he pull it off, but he did it for next to nothing in terms of cost to the franchise.

Worst Red Wings Trade Detroit trades: Patrick Eaves Calle Jarnkrok 2014 46th overall pick ↔ Nashville trades: David Legwand

It’s not so much that David Legwand was, at best, mildly successful in Detroit. Nor was it that the Wings acquired Legwand as a rental for the NHL Playoffs only to get eliminated in five games by the Boston Bruins in the first round. For me, the trade was more about what Holland gave up and the success those players have had post-Detroit that is so disappointing about this deal.

David Legwand (Don McPeak-US PRESSWIRE)

Holland moved Wings prospect Calle Jarnkrok and fourth-liner Patrick Eaves to the Nashville Predators to acquire Legwand at the 2014 trade deadline.

Jarnkrok quickly worked his way into the Predators’ top-nine forwards, scoring two goals and nine points in 12 games that season. Since then, he’s remained in Nashville’s lineup, as the 24-year-old has played in 74 games and 81 games in each of the last two seasons, totaling 23 goals and 48 points.

Eaves didn’t have any success in Nashville and only played five games. However, he did sign with the Dallas Stars where he’s found success. For long stretches, the former Wing played on the Stars’ top line with superstars like Jamie Benn and Tyler Seguin. Eaves’ grit and heavy forecheck opened up space for others to produce on the top line. In return, he was been the beneficiary of a boost in ice time—including power-play minutes—and a resurgence in points, scoring 25 goals and 44 points in 101 games with the Stars.

Brandon Peleshok

Best Red Wings Trade Detroit trades: Anders Eriksson 1999 23rd overall pick 2001 29th overall pick ↔ Chicago trades: Chris Chelios

Arguably, some of Ken Holland’s best trades have involved adding that last, integral piece to the Red Wings’ blueline. With respect to both Mathieu Schneider and Brad Stuart, no defenseman acquired by Ken Holland had a bigger impact than Chris Chelios.

Chris Chelios Trade made by Ken Holland of the Detroit Red Wings.

Few could have predicted that the (then) 37-year old blueliner would go on to play 10 seasons in Detroit, accumulating two Stanley Cups and 152 points in his 578 games with the team. While his ability to contribute offensively slowed by that time, Chelios offered the Wings defensive stability, leadership and a physical edge.

At the end of the day, the trade didn’t cost the Red Wings much. Eriksson played three seasons in Chicago before the Blackhawks traded him, and neither of their first round selections (Steve McCarthy and Adam Munro) had a lasting impact with the team. Not bad for a player who, even today, remains a part of the Red Wings’ organization in a part-time assistant coaching position.

Worst Red Wings Trade Detroit trades: Mattias Backman Mattias Janmark 2015 49th overall pick ↔ Dallas trades: Erik Cole 2015 73rd overall pick

Hindsight is 20/20, but it’s tough to ignore the way the Erik Cole acquisition turned out. The abrasive forward was having a solid season with the Dallas Stars, putting up 18 goals and 15 assists through 57 games. Unfortunately, Cole played in just 11 games before suffering a spinal contusion, and has not played in the NHL since.

Mattias Janmark. (Credit: Michael Connell/Texas Stars Hockey)

Mattias Janmark has proven a solid acquisition for the Stars. Now in his fourth season with the franchise, Janmark has been able to move up and down the lineup for the Stars and serve as a valuable penalty killer.

This article was originally published in August, 2016.