Damian Lillard Will Sign With Boston Celtics In Free Agency

One year ago, Boston Celtics fans anticipated potentially celebrating a second consecutive championship. The team held the No. 2 seed in the Eastern Conference for much of the season, positioning those hopes as realistic. However, a torn Achilles suffered by Jayson Tatum during the playoffs, combined with poor team performance in the second round, led to an earlier-than-expected elimination.

This injury significantly altered the Celtics' long-term plans, resulting in recent salary dump trades involving Kristaps Porzingis and Jrue Holiday. The team is now focused on contending again in the 2026-27 season. Analyst Steve Bradshaw predicts the Celtics will make a move aligning with this timeline by acquiring Damian Lillard.

Lillard, like Tatum and Tyrese Haliburton, suffered an Achilles injury during the playoffs and is expected to miss the majority of the 2025-26 season. His greatest impact is projected for the years beyond 2025-26. Bradshaw argues this timeline matches perfectly with the Celtics' strategy to reload for the 2026-27 season, especially since Tatum is also likely to miss the entire 2025-26 season. Acquiring Lillard would provide backcourt help when both stars are healthy for the 2026-27 campaign, though finances present a significant roadblock.