My personal opinion is that it is a little unfair to assume that Tippett can't play well with others in a decision-making circumstance.
Let's look at the timeline here:
Maloney starts as GM in 2007 - every decision that is made is likely made between himself, owners, and Gretzky, where Gretzky gets the lion's share of input.
From 2009 up until the purchase of the team by IA, the NHL gave him a budget and that was it. I am assuming that the NHL stayed very hands-off in terms of deals, so a lot of the decision-making was balanced out between Tippett and Maloney inputs, probably with them agreeing on more than just a few things. I don't think that Tippett put a gun to Maloney's head regarding Ribeiro. Rather, both Tip and Maloney agreed on that move.
Now, with ownership in place, there is another mind in the group, but these guys aren't the NHL and approaching the "one year at a time" philosophy.
As someone posted, I think that Maloney's downfall was that he didn't adapt and to be honest, he never really had a true "plan" in place. The only time he had a plan was when the team went down the tubes in 14-15 season. And that plan was the firesale for the rebuild. Even if he did have a plan, when the team was without an owner, the plan didn't need to be laid out to anyone, as it was almost a season-by-season basis in terms of working with the NHL. That likely exposed itself early on in ownership and the last two years when we had individuals putting together a three-five year vision.
I get that Tippett has favored a more veteran and experienced team, but I also think that the analytics that he uses (whether similar or dissimilar to Chayka's) at least shows an initiative of asking the 5 W's with regard to player personnel now and in the future. I strongly doubt that Tippett is going to strong-arm certain scenarios, rather that the collective group-think will have an analytical focus for the now and future, whereas the detracting voices in the room in the past would not have had an analytical approach toward particular players. This time around, the detractors will have some analytics behind their decision and will make it easier to order, compare, and evaluate players.