Best and worst trades of the Detroit Red Wings during Ken Holland's era

His decisions shaped the team during its most successful years and transition periods. Here's a look at some of the best and worst trades made by Holland during his time with the Red Wings:

Best Red Wings Trades:
- Chris Chelios from Chicago Blackhawks (1999):

Trade: Detroit acquired Chris Chelios from the Chicago Blackhawks in exchange for Anders Eriksson and two first-round picks (1999 and 2001).

Impact: Chelios played ten seasons in Detroit, winning two Stanley Cups and providing the team with veteran leadership, defensive stability, and a physical edge. The cost was relatively low, as neither of the first-round picks (Steve McCarthy and Adam Munro) significantly impacted Chicago.

- Pavel Datsyuk Contract Trade to Arizona Coyotes (2016):

Trade: Detroit traded Pavel Datsyuk's contract and the 16th overall pick in 2016 to the Arizona Coyotes for Joe Vitale, the 20th overall pick, and the 53rd overall pick.

Impact: This trade allowed Detroit to free up significant cap space, which was critical for maintaining roster flexibility. While the decision to move down in the draft could be scrutinized, Holland saw the ability to offload Datsyuk's cap hit without sacrificing top prospects as a savvy move.

Worst Red Wings Trades:
- Kyle Quincey from Colorado Avalanche (2012):

Trade: Detroit acquired Kyle Quincey from Colorado in exchange for Sebastian Piche and a first-round pick.

Impact: Quincey provided some depth but was not worth the high cost, especially considering that the first-round pick turned into Andrei Vasilevskiy, a future star goaltender for Tampa Bay. The trade is often criticized as a missed opportunity for Detroit.

- David Legwand from Nashville Predators (2014):

Trade: Detroit traded Patrick Eaves, Calle Jarnkrok, and a 2014 second-round pick to Nashville for David Legwand.

Impact: Legwand was a rental player with limited success with the Red Wings. The real issue with the trade was the loss of Calle Jarnkrok, who went on to have a productive NHL career, especially as a valuable top-nine forward for the Predators. This trade is often cited as a significant overpayment for a short-term rental.

- Erik Cole from Dallas Stars (2015):

Trade: Detroit acquired Erik Cole and a third-round pick from Dallas in exchange for Mattias Backman, Mattias Janmark, and a second-round pick.

Impact: Cole's tenure with the Red Wings was cut short by a spinal contusion, and he never played in the NHL again. Meanwhile, Janmark developed into a solid NHL player for Dallas, making this trade a clear loss for Detroit in retrospect.

What Could Have Been:
One of the most debated near-moves during Holland's era was a potential trade of Pavel Datsyuk for Scott Gomez in 2007.

Fortunately for the Red Wings, the trade never materialized, and Datsyuk remained in Detroit, becoming a key player in their 2008 Stanley Cup run. In contrast, Gomez's career declined rapidly, highlighting how crucial it was that this deal didn't happen.

These trades highlight the highs and lows of Holland's tenure as GM and reflect the challenges of managing a team through various stages of contention and rebuilding.

Source: The Hockey Writers
Best & Worst Trades in Ken Holland's Red Wings Tenure

Source: NHL
Ken Holland Bio