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When Steve Yzerman rejoined the Red Wings in 2019 and began a rebuild in the Motor City, many wondered how long it would take the NHL Hall-of-Famer to build a powerhouse like the one he’d built for the Lightning. Some seven years into that tenure, the questions within the organization have shifted, and one narrative has become clear. Yzerman’s plan has been a colossal disaster thus far, raising the question of how much more time he will get to turn around a Red Wings team that hasn’t been in the playoffs in a decade.

It’s not as though Yzerman hasn’t built decent teams. The Red Wings have been competitive in the Eastern Conference over the past handful of seasons but haven’t made the postseason, despite being in a position to secure a playoff spot. This year, the Red Wings spent most of the season in a playoff spot, only to fall apart at the end and miss by just a few points. This pattern repeated in previous years as well. So, what happened, and what needs to happen next?

When Yzerman took over, he did a terrific job pivoting to a rebuild and trading roster players for future assets. The Anthony Mantha trade with Washington in 2021 was a home run, acquiring Jakub Vrána, a first-round pick, and a second-round pick. He also made the 2023 Tyler Bertuzzi trade, which brought in another first-round pick, and the Filip Hronek trade with Vancouver, which brought in an additional first- and second-round pick.

The Hronek trade didn’t work out well for Detroit, but it was an okay move given where the team was. Not long after, Detroit acquired forward Alex DeBrincat from the Ottawa Senators, a move that suggested Yzerman felt the team was ready to move from rebuilding to trying to win now.

He also did well to identify core players to build around through trades and the draft, before locking them into reasonable long-term deals. Dylan Larkin, Moritz Seider, and Lucas Raymond are all signed to solid long-term contracts, with Seider and Raymond being Yzerman draft picks. Overall, it’s hard to find fault with Yzerman’s early work, as he laid a solid foundation to build on.

Where Yzerman has gone wrong is in his pursuit of veteran talent to insulate his younger stars; and to say he’s gone wrong is putting it very kindly. Yzerman has failed at almost every turn in his attempts to acquire veteran players, both in trades and in free agency.

The summer of 2022 was an especially egregious period for the Red Wings’ salary-cap structure, as Yzerman signed defenseman Ben Chiarot and forward Andrew Copp to bloated multi-year deals that have been awful value for Detroit. Chiarot received a four-year deal worth $4.75MM per year, which was a lot of money for a defenseman who generally makes his defense partners worse and is constantly on the wrong end of the possession game. Chiarot had his strengths, too, but given how he’d fared in his career when asked to do too much, it was inevitable that the results wouldn’t be good in Detroit.

Copp, on the other hand, signed a five-year deal worth $5.625MM annually and came to Detroit with a lot of promise and versatility. However, he had only one season with over 20 goals and 50 points, so expecting him to be a consistent offensive contributor was too high a bar for Copp, which is part of why his run has been disappointing for Red Wings fans. The issue was ultimately that Copp was paid to be a top-six forward, but he slots better as a middle-six option.

Yzerman’s poor work in free agency continued in 2023 when he signed UFA defenseman Justin Holl to a three-year deal worth $10.2MM, which proved disastrous for Detroit. Holl recorded two goals and 11 assists in 111 games as a member of the Red Wings and had to be dealt to St. Louis at the deadline as part of the Justin Faulk trade.

The Holl signing, and even the Faulk trade to a lesser degree, highlight a major flaw in Yzerman’s building strategy, as he has consistently tried to patch together his defense core with veteran players who don’t move particularly well and are on the backside of their careers. Chiarot, Faulk, Holl, and especially Jeff Petry all highlight this issue. In fact, Yzerman’s moves on his backend could be the ultimate undoing of his tenure in Detroit, as he has sent Jake Walman and Hronek out the door and essentially replaced them with Chiarot and company.

The Walman sequence was an especially curious error. Walman was dealt to San Jose along with a second-round pick, only to be traded less than a year later by the Sharks to Edmonton for a first-round pick. The move gift-wrapped two premium draft picks for the Sharks, who paid 50 games’ worth of Walman’s $3.4MM contract in exchange for them. Edmonton eventually signed Walman to a regrettable seven-year extension, but the real loser in the sequence of events was Detroit, which traded Walman along with an asset only to see him traded for an asset. The Walman trade tree is a real indictment of Yzerman and company’s pro scouting, which has failed Detroit in free agency too often.

The defensive contraction and the free agency failures have been Yzerman’s downfall thus far in Detroit, and even though he has won many of the trades he’s made, he hasn’t been able to undo some of the damage he’s done in the summertime and now the Red Wings are at a crossroads where many teams who never rebuilt (Washington and Pittsburgh) have lapped them, even though Detroit went through a long painful rebuild.