Trail Blazers immediate free agency move No. 2: Re-sign their own key FAs
Depending on what happens with free agency move No. 1, this could get very tricky and very expensive. If Portland is able to land Draymond, it will likely be in the $25 to $30 million range per year. Jerami Grant is expected to sign a contract worth about $30 million annually.
If the Blazers want to stay under the luxury tax, it’ll take some “serious cap wizardry,” as Amick said.
It would also be a wise idea for Cronin to bring back guard Matisse Thybulle. Adding Green and re-signing both Grant and Thybulle would bring balance to an offense-heavy roster. All three are more than capable defenders; Portland could use as many of those as possible.
Re-signing Grant at $30 million per year and Thybulle at $7 million while renouncing all of the team’s other free agents would bring the Blazers to about $2.4 million below the luxury tax. Signing Draymond would put Portland far past that.
In order to stay below the tax and bring Green aboard, it would require the Blazers to trade Anfernee Simons and perhaps Jusuf Nurkic as well. Whether Portland decides to go all-in on a Draymond signing or not, the organization should at least find a way to bring back Grant and Thybulle.
Not only would that likely solidify Lillard’s decision to stay in Portland, it would be a huge roster boost defensively for a team that desperately needs it.