I'd love for a deal like this to happen, but I don't think it will.
For matching purposes it would be easier to include a non guaranteed like Pressey, the problem is we would need to pick up his contract by Wednesday, so if we were going to trade him we would presumably need to do it before then so the team could waive him in time.
Since Ainge is all about acquiring assets, I would just hold our assets and then make a run at him next year when we have a lot of money to spend.