The rumors of Kyrie for Simmons are interesting. You can make a pretty good case for it considering the on-court potential alone. Simmons as the third or fourth scorer, making plays for all those shooters and shoring up their defense, would make a lot of sense. Nobody would ask him to take jump shots. Kyrie could bring the shooting and creation Philly needs and they’ve got plenty of defenders. But then both teams probably have to think hard about whether thye want to trade one headache for another. Does BKLN want to risk Simmons going into a freeze in the playoffs (passing up a dunk…?); does Philly want to see Kyrie deciding he needs to go burn some sage or going sour when the Philly fans do what Philly fans do? Of course they’d also rather not help a rival that’s a real threat to their title hopes - and that may be the biggest obstacle. Both teams would rather find a different trade partner.
But, just as a thought exercise, if if the trade did happen I think it would be won by BKLN, pretty handily.