I am reserving judgement on Simons. It is a problem in the playoffs if a core rotation player is weak defensively. But that doesn't mean he can't help the team. As to Lillard in place of Simons or in addition to Simons, I think one or the other and I would rather have Lillard for a couple of seasons at $6M per than Simons at 4 years and $125M or whatever he might get (that is about what Poole and Herro got). I can't see having both. If we are able to sign Lillard, then it makes it an easier decision to trade Simons (at the deadline).
But I am not ready to rule out either Lillard or Simons due to defense. Curry is not exactly an all defensive player. Neither is Mitchell or Brunson. There can be a place for players like this on very good teams, up to a point. If Sam Hauser can play sufficient defense, I see no reason that Simons can't (admittedly on smaller players).
Is Simons a worse defender than Pritchard? Genuine question. I have the same reservations about PP based on his performance in past playoff series.
Fair question. I have not seen enough of Simons to say either way. Most seem to be pretty down on Simons' defense, for what that is worth. Pritchard is scrappy on defense, but has many of the same limitations otherwise that Simons has. Maybe Simons can be more of that too if he just tries or needs to in order to get minutes (or a big contract).
As I have said, I have not given up on him. There have been too many cases where I think I know what BOS is getting in a trade and then once the player is here, I am surprised one way or the other. If this was a couple of seasons ago, my impression was that Simons was an up and coming player, right there with Tyler Herro or Jordan Poole. Then he kind of disappeared. Poole looked pretty good on GSW and then pretty bad on WAS. So my expectation is that Simons will be a better player on BOS than he was on POR. Hopefully enough better that he generates some decent trade interest.