4. Trading Jrue Holiday
Jrue Holiday needed to be part of the trade that sent Lillard to the Bucks. However, the 33-year-old point guard made no sense on a Blazers roster that already included Henderson, Simons and Shaedon Sharpe. Holiday surely wanted no part of a rebuild either after playing on championship-caliber teams and winning the 2021 NBA Title in Milwaukee.
Only a few days after sending Dame packing, Cronin flipped Holiday to the Boston Celtics for Malcolm Brogdon, Robert Williams III, a 2029 unprotected Boston first-round pick and a 2024 top-four protected Golden State Warriors first-round selection.
Brogdon is staying in Portland for now, but there’s a chance he gets traded at or before this year’s deadline, which would expand the Lillard trade even further, but grabbing additional assets by acquiring Holiday and then sending him to Boston was a shrewd move by Cronin.
When he’s healthy, Williams is an all-defense caliber center. Brogdon is a veteran guard who will be an adult in a young backcourt room as long as he remains with the Blazers. The 2029 unprotected first could end up being valuable given the question marks that could follow the Celtics over the next five seasons.
Holiday will be 38 and likely retired, and will Jayson Tatum and Jaylen Brown still be around?