The Trade That Former Red Wings GM Ken Holland Regrets


Ken Holland was nothing if not aggressive as general manager of the Red Wings. He wanted to win, and he wanted to win now. If that meant mortgaging the future, so be it. He'd deal with the future later. 

That approach was ultimately his downfall in Detroit, but that's not why we're here. 

Holland was elected to the Hockey Hall of Fame Wednesday because his vision in the front office helped lead the Wings to four Stanley Cups. 

Congratulations Kenny! #HHOF2020

— Detroit Red Wings (@DetroitRedWings) June 24, 2020

Holland, as he'll have you know, sent two first-round picks and another former first-rounder to Chicago at the 1999 trade deadline for Chris Chelios. Chelios would play a pivotal role in Detroit's championship in 2002.

He sent a second-rounder and a fourth-rounder to Los Angeles at the 2008 deadline for Brad Stuart. Stuart would play a pivotal role in Detroit's championship in 2008. 

Of course, swing as often as Holland and you're bound to miss. Especially later in his tenure, as the team's dynasty was fading, he made some moves he'd probably take back. Kyle Quincey, anyone?

But to Holland, those aren't the missteps that stand out. 

Asked on a conference call Thursday about the most difficult trade he's made in his career, Holland pointed to his first: Mike Vernon to San Jose for two second-round picks. (Detroit would later trade those picks in separate deals.)

"I would not do that today," Holland said. "I’d keep the depth in goal and I’d let the goalies and coaches decide who’s going to play."

It was the offseason of 1997, and Holland had just been promoted to GM. The Wings had just won the Cup. And Vernon had just been named MVP of the playoffs after going 16-4 with a .927 save percentage and a 1.76 goals against average. 

But Detroit also had Chris Osgood, who was nine years younger and had begun to supplant Vernon in net. 

"They both wanted to be No. 1's and I decided to go with the younger guy," Holland said. 

It worked out fine for the Wings, who won the Cup again in 1998 with Osgood in net. Still, Holland considers it a mistake. He told Vernon so himself after the goalie sent him a congratulatory text on Wednesday: 

"I texted (him back) and I said, 'I wouldn’t do that deal today.' I said, 'I’d have you and Ozzie battle it out and I’d have depth in net.'"

"I was young," Holland said. "When you make decisions as a manager, you analyze everything and hope that most times they work out. But sometimes they don’t. As you get more experience, whatever job you do, you look back and you might handle situations differently."