Is Holland a great GM or is Holland a terrible GM? Both statements are lies and both are truths. Why is that, like any other GMs and even his Oiler predecessor, he has had trouble during the cap era. The question is how much is his fault and how much has he learned.
One of the greatest things of his Red Wings dynasty days and passed was the ability to assess talent and draft. He has done well in that matter. No one can argue and yes drafting involves luck in later rounds but when you draft talent, raw talent and raw skill in the later rounds it increases the chances of that becoming a home run. He has done that well. So with the recent influx of prospects from Keith Gretzky and Holland, the Oilers can hopefully replenish and create a great farm.
The next part is the problem. I am sure many of the mistakes are because of Holland not having a backbone and scared to admit his dynasty days were ending. Holland as many know signed and signed and signed again the players of days past to terrible contracts hoping to catch lightning in a bottle only to see the team continue to wallow away. These are moves of a scared and desperate GM and a terrible one for that time. Holland has remedied some of that with some contracts slowly clearing for Yzerman. So has Holland learned from his mistakes, time will tell.
The next avenue is trades, Holland is not a maniac trader, he is a patient and concise one, atleast from seasons past. He has kept many players past deadlines if he didnt get what he wanted, he traded Tatar for a 1st, 2nd and 3rd round pick. That has to be considered a win. The problem lies herein, the Oilers desperately need changes and trades are a route that must be taken. How is he going to get out of Oiler cap hell? Can he and will he? I say will he because he is of the old guard, and maybe he believes in Lucic like everyone's favourite Chia pet. Or maybe he has a plan.
So after looking at the main three areas, you can why is easy to say Holland is both great and terrible at the same time. Can he be successful? Yes but he needs to do the right moves and learn. Lamoriello for the most part helped the leafs in his 3 years, yes he was under guidance but it showed learning. Can Holland do the same with full autonomy? Maybe that's why Holland wanted control. Maybe he knows the team needs help all across the board. He needs to clean ship, he needs to remove the old guard that doesnt want change, he needs to hire a capologist, a young assistant GM that has great potential, and he needs to create a culture based on skill, speed, size then grit not the other way around. He needs to have a plan. A good plan and execute it. Can he? Of cpurse he can he is one of the GMs that definitely can. The really question is will he?