I've never said this. I've always said I've felt he would never sign him to a long-term deal that Smart would agree to signing. Comparing the 4/$50m-ish deals is not in the same league as Sheed or Jermaine on a 2-year MLE......Ainge would absolutely sign Smart to a 2-year MLE so I don't understand the point you're trying to make.
No, he really hasn't overpaid and Yes, he has had other contending teams.. He signed Shaq, Posey, Nate Rob, Marbury, Cassell, PJ, and Eddie House to fill these roles while having 2nd round picks like Baby and Powe along with a couple MLE guys. He's never signed a 4/$50m contract for a 3rd or 4th guard. He let Perkins go, let Posey go, let Baby go.....rather than locking them into long term deals. The only "overpays" I see are Sheed and Jermaine who again were on 2-year deals at the MLE which is reasonable not an overpay. 4/$50m is an outrageous overpay for the role Smart will have on this team imo.