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How can the Blazers contend with Lillard's new supermax?

How can the Portland Trail Blazers make a Damian Lillard supermax contract work for them?

Lillard and the Blazers are set to agree to a four-year extension, currently projected to be worth $196 million, on the first day it could be offered. The extension would kick in during the 2021-22 season, after Lillard's current contract expires, and its value wouldn't be determined until the salary cap is set two years from now.

The challenge now is for the Blazers to maintain a competitive team around Lillard once his salary jumps to an expected average of nearly $50 million per year.


How well can Lillard be expected to age?