Damian Lillard may have moved on from Portland, but his fingerprints remain on the Trail Blazers’ latest big move. According to NBA insider Jake Fischer, Lillard reached out to Jrue Holiday when Portland re-acquired him this offseason, helping ease the veteran guard’s transition back to a city he briefly called home during 2023’s blockbuster trade. Lillard reportedly spoke highly of Portland as a franchise and a city, shaping what appears to be a smooth welcome for Holiday.
This time, the Blazers are determined to keep Holiday. Unlike his short stint before getting flipped to Boston in the Lillard trade, Portland views Holiday as a cornerstone for their postseason ambitions. The front office believes that adding a championship-caliber veteran is key for a roster brimming with young talent still searching for playoff success.
Holiday’s experience, especially after helping the Celtics win the 2024 title, could be the stabilizing force Portland’s backcourt needs. Though his offensive numbers dipped—averaging 11.1 points, 4.3 rebounds, and 3.9 assists per game—his elite perimeter defense remains among the NBA’s best. His leadership could accelerate the growth of younger teammates while giving the Blazers a much-needed defensive anchor.
Portland’s strategy seems clear: integrate Holiday with the team’s young core, shore up depth at the forward position, and hope health is on their side. If that formula holds, they believe a playoff berth is within reach. While Jrue Holiday’s future was once uncertain in Portland, thanks in part to Lillard’s quiet endorsement, he now stands at the heart of the franchise’s playoff push.
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