Solid read. The issue I have is that DeMar is firmly a 3rd-tier player that benefits from always having the ball in his hands. Add in that Casey refuses to criticize or curb his penchant for hijacking the offense to get his shot off, and it can quickly turn into a player believing they're much better than their statistics and results indicate. We can talk about how the % of the cap he would theoretically take up is relative to the future market value players of ilk will have when the cap increases, or we could have an honest discussion about what gifting $20M+ annually to him would mean for roster construction going forward.
He's been a good citizen of the city, kept his nose clean, worked hard, and showed up every night. But he's not good enough. He can't carry a team through the playoffs, much less the regular season shooting a decent percentage for a SG. I'm already hearing a lot of, "Well, somebody is going to pay him, so it might as well be us.". That never ends well in the NBA. Can he be the best player on a championship or NBA Finals team? No. Aside from the flashes of hitting the low-percentage shots he lives and dies on, we have seen nothing to indicate that he'll suddenly turn a corner after 6 years in the league.
I would stop short of calling this another Bosh situation; say what you will about CB4, but he was a perennial All-Star and a legit top 3 power forward during his Toronto days. That Colangelo repeatedly botched attempts to build around him says more about the former GM than it does about Bosh. I won't rehash all of DD's shortcomings here, but Masai must realize that building around one of the least efficient wing scorers in the league is a fool's errand. Will he get paid? Of course he will. But I think we can agree that if DD is this team's 1st or 2nd best player, the ceiling of the Raptors tops out at a second round exit. That's good enough for some fans who just want to win something of consequence, but if the endgame is a championship, DD's time in Toronto is drawing to a close. 3 playoff wins total in 6 years? Thanks, but I'll pass.