Holland's reputation was built in a different era with completely different circumstances. No salary cap, an owner willing to sign whatever check Holland presented him with, and a team that was already a contender and able to attract good free agents when he assumed his role. And the scouting landscape was also completely different. Stories like Detroit drafting Datsyuk late being the only team who saw him play just don't really happen anymore. To be clear, he deserves the reputation he built over the mid-90s to mid-2000s. He was an important part of the organization for several years before his tenure as GM began. And he took the hand he was dealt and made the most of it. He is one of the most important influences, perhaps the most important, in one of the greatest eras in Red wings history. He was the right man at the right time.
But he just isn't made for this era. He had a few good years in the salary cap era but that was 90% due to Lidstrom, Datsyuk, and Zetterberg, relics from that earlier, dominant era. His drafting in the cap era has not been great, granted he traded away a lot of 1sts. But after Kronwall he basically didn't draft another top player for a decade until Larkin came along. His free agent signings and trades were atrocious in the worst instances, and sad vegetable farts in the best instances. Uninspired and conservative to a fault, and the team on the ice reflected that. The years after Lidstrom retired until Holland's departure were the worst in a long time. An excuse is often made for him that he was ordered to continue the playoff streak for Mike Ilitch's last years. That is a relevant point to raise, but I don't find it sufficient to excuse the state the team ended up in. He may have been ordered to consider the playoff streak a priority, but I really doubt he was micromanaged in any meaningful way. He was just given a priority and the execution is up to him. So the hanging onto vets well past their useful years, the handcuffing of the team with terrible long term contracts, and the few draft picks amounting to difference-makers are all 100% on Holland.
He had a legendary decade and a half as GM, and his place in the HOF is warranted. But the game has passed him by and he should just retire before he tarnishes his image more. There is a small chance he is able to get a Cup with Edmonton, he has the best player in the game and another top 3-5 player in the league on his roster. But the results so far don't look promising. And his tenure in Edmonton is looking like a continuation of 2011-2018 Holland and that doesn't bode well for the Oilers. I shudder to imagine an alternate reality where Yzerman never left Tampa and Holland is still the GM in Detroit today.
