Trouble is, to match salaries you'd have to give up at least one of Grant, Nurk or Hart. Of the three, I'd be most intrigued with Nurk and have Simmons play a sort of Sabonis role (he'd instantly make us super-switchable on D, too). But I don't know if that would interest Brooklyn.
In order to take on Simmons out-sized salary for someone who is essentially a role player with serious limitations, I'd also want a number of picks. Want to get rid of him? It will cost you.
For what package though? If we could get him cheap sure, but hell I'm not sure I'd trade Simons straight across for him at this point...
Nice question. Simmons straight up for Simons is absolutely a HUGE risk. Probably far beyond what Cronin would reasonably consider. Simons is good, getting better, and if it's him vs. CJ rejuvenated to Simons' age and for Simons' $$$, it's not even close. Simons. If someone disagrees, okay. I just don't see it as remotely close. Simons is a dude. A 6'3 dude. Simmons has never been a favorite player of mine, but what he can do is more valuable than what Simons does for the Blazers especially with the arrival of Sharpe (and what I'm guessing he'll be in two years). Nurkic + Hart for Simmons? Risky. Because. Of. Simmons. Comparing the impact of good Simmons to Rodman for the Bulls relies upon support structure and knowing what's coming in. Dame as the leader is a serious thing. Not going to happen. Moot point. But your question is reasonable. I'm sure I'm in the wrong on the reality of Simmons and his issues and as a teammate. What the Blazers have now? Not good enough.
