Ken Holland’s Greatest Hits and Biggest Flops of the Salary Cap Era
Ken Holland is one of those NHL GMs where you say his name, and it comes with baggage—good and bad. You get “Three Cups in Detroit!” followed quickly by “Darnell Nurse got WHAT?!”
He’s been in the game forever, built one of the best dynasties in NHL history with the Detroit Red Wings, and helped bring Edmonton back from the chaos of the Chiarelli era. And now it seems that he will be the next General Manager of the Los Angeles Kings.
Let’s rewind the tape—Greatest hits to Biggest flops. BUT, we’re only looking at his resume in the salary cap era where you can’t just sign nine Hall of Famers in on a dare from your drunk cousin.
Mr. Holland’s Opuses
1. Signing Zach Hyman (7 years, $38.5M, 2021)
This looked like a bit of an overpay at the time. It’s now a certified steal. Hyman has become a true core player for the Oilers—hard nosed, sometimes elite, and built for the playoffs. He scored 54 goals in 2023–24 and has been everything the Oilers needed: a forechecking machine, a net-front menace, and a no-ego complimentary piece who wants no part of the McDrai spotlight. Holland nailed this one.
2. Trading for Mattias Ekholm (2023 Trade Deadline)
Holland needed to fix the Oilers’ blue line, and he didn’t just patch it—he reinforced it with viking steel. Trading Tyson Barrie, prospect Reid Schaefer, and picks for Ekholm gave Edmonton exactly what it lacked: an actual #1 defenseman, who could actually defend and actually be worth his price tag. Maybe he learned from prior mistakes? More on that later. Since arriving, Ekholm’s been a rock. This move really changed the way the league looked at the Oilers. They didn’t need to score 6 or 7 goals nightly anymore and it’s fair to say Ekholm’s commitment to defense rubbed off on (most of) his team.
3. Signing Brian Rafalski (2007, 5 years, $30M)
In 2007, Nicklas Lidstrom needed a right-shot defensive partner to play with. Holland swiped Scott Niedermayer’s former partner in New Jersey and it paid off BIG. Rafalski put up 55 points, including 10 power play goals, earning him some Norris votes that season. More importantly, he helped them win the Cup in 2008 and return to the Final in 2009.
4. The 25-Year Playoff Streak
Okay, so I said nothing from the pre-cap era, but 11 of the 25 consecutive years where the Red Wings made the playoffs were after the lockout of 2005. Say what you want about how it ended, but the dude kept the Wings in the mix for a quarter century. That takes a great deal of work, both at the pro level and the developmental level, not to mention vision, patience, and no small amount of ego management.
5. Trading Milan Lucic for James Neal (2019)
It looked like a “change of scenery” swap, but It became one of Holland’s sneakier wins.
Lucic (AAV $6M): Big, slow, unmovable (on the ice and on the books).
Neal (AAV $5.75M): Slightly faster, slightly younger, and — initially — slightly more productive.
Lucic had four years left and a full no-move clause. Neal at least scored 19 goals in his first season before tapering off hard. Edmonton eventually bought him out in 2021, spreading the cap pain through 2025–26. But Lucic? He stayed glued to Calgary’s books for the full deal and remained a $6M anchor with diminishing returns. No one “won” this trade in the long run — but Holland at least maneuvered his way to the slightly less painful end of it.
OMG, they fleeced Kenny!
1. Darnell Nurse Extension (8 years, $74M)
Woof. History has shown that you can probably defend any move to an extent, but even Oilers fans have struggled to lie to themselves on this one. The moment Seth Jones got his mega-deal, Nurse's camp saw dollar signs, and Holland blinked. $9.25M per year for, at best, a second-pair D-man with first-pair aspirations — and the Oilers have been paying for it ever since. It says a lot that the cap ceiling is about to skyrocket and this is STILL going to be one of the worst contracts in hockey.
2. Signing Jack Campbell (5 years, $25M)
Good guy, Jack Campbell. I bet he misses Los Angeles every day. In a summer that featured one of the shallowest pools of available goaltenders in recent memory, Holland backflipped into the deep end and landed belly first. Coming off a 31-win season with Toronto, Campbell was about to cash in. Edmonton desperately needed a goaltender as Mike Smith finally decided he had enough, so in some ways, Holland had to make this kind of move. That being said, freshly minted Stanley Cup Champion Darcy Kuemper was there for the taking at a very similar number. Ken chose poorly.
3. Signing Justin Abdelkader (7 years, $29.5M)
I’m picking on Abdelkader here, but Holland had a glut of head-scratching depth contracts in Detroit. For example he tried to replace Pavel Datsyuk with Frans Nielsen. That’s like replacing a Michelin-star chef with a guy who thinks microwaving fish is okay. It was a reach from day one — and by year three, it became dead weight. Others like Helm, Glendening, Ericsson and others were probably viewed as “culture setting” type guys, but goodness, Ken, how many did you need? The loyalty was noble, I guess? But the cap implications were brutal. Detroit’s rebuild had square wheels for years because of it. By the way, the Red Wings bought out Abdelkader’s contract in 2020 and are still paying him to this day.
4. Trading the pick that became Andrei Vasilevskiy (2021 Trade Deadline)
At the 2012 trade deadline, Ken Holland decided it was time to bring Kyle Quincey back into the Red Wings fold — a guy he originally drafted in 2003 and had since watched bounce around the league like a rental car. The goal? Beef up the blue line for a playoff run. The cost? A first-round pick that turned into *checks notes* two-time Stanley Cup Champion, Conn Smythe Winner, and two-time Vezina finalist Andrei Vasilevskiy. The GM on the other end of that deal? Steve Yzerman — Holland’s former captain, front-office protégé, and eventual successor in Detroit. Oh, the humanity.
5. NOT signing Holloway and Broberg before Bowman Fumbled Them
I get it… this isn’t totally fair. It was Stan Bowman and friends who ultimately decided not to match offer sheets for Dylan Holloway and Philip Broberg. But the opportunity to tie up these loose ends was there for Holland. It kind of feels like he said, “Let the next guy deal with it.” From a Kings perspective, that’s a little scary. Holland is nearing 70-years-old and every indication is that his next GM gig will be short-term. So, you know… the “next guy” and his potential situation is sort of important in Los Angeles.
Like most NHL GM’s in history, Holland’s resume is filled with both wins and losses. He’s a unique case in that he was arguably the best GM in hockey between 1997 and 2010, but struggled in his later years. His ability to draft franchise-altering players from seemingly out of nowhere and the fact that he is the only GM in NHL history to win a Stanley Cup in both the Pre-Cap and Salary Cap eras landed him in the Hockey Hall of Fame in 2020.
The question is: How will he fare in LA, with a team that is desperate to win now. Let us know on Twitter/X!
