One of the most talked-about moments in this year’s NBA free agency was Damian Lillard’s return to the Portland Trail Blazers. On Thursday, ESPN’s Shams Charania reported that the veteran guard had signed a three-year, $42 million contract with Portland, marking a homecoming after two seasons with the Milwaukee Bucks.
Despite Lillard’s continued All-Star level of play in Milwaukee, the results were underwhelming. The Bucks, paired with Lillard and Giannis Antetokounmpo, failed to advance past the first round of the playoffs in back-to-back seasons. The short-lived experiment made it clear that the partnership hadn’t produced the expected success.
With the Bucks opting to waive Lillard early in free agency to create cap space for Myles Turner—who signed a four-year, $107 million deal—Lillard had the opportunity to test the open market. Though he received mid-level and minimum offers from contenders like the Boston Celtics and Minnesota Timberwolves, he ultimately chose to return to Portland.
Kendrick Perkins: “His heart was always in Portland”
On Friday, former NBA player and analyst Kendrick Perkins weighed in on the news during an appearance on First Take. Perkins shared his joy at seeing Lillard back where he belongs.
“I was surprised, but I am happy,” Perkins said. “It’s been a dark cloud, it’s been raining in Portland since Damian left—and now the sun is shining.”
Perkins went on to say that even while Lillard played for Milwaukee, his mind and heart never left Portland:
“Physically he left, but mentally he was never gone. His heart was always in Portland. His family lives in Portland, his kids are in Portland, and most importantly, this is who Dame is. Dame is not one who runs and ring chases… It was out of character for him to request a trade.”
“Physically he left, but mentally he was never gone. His heart was always in Portland.”@KendrickPerkins shares his thoughts on Damian Lillard going back to Portland 🔥 pic.twitter.com/eQeZbZvT22
— First Take (@FirstTake) July 18, 2025
Family was the driving force behind Lillard’s return
According to Shams Charania, family was the most significant reason for Lillard’s decision to rejoin the Trail Blazers. The star guard prioritized being closer to his children and loved ones, who reside in Portland.
“Being back with his three kids was by far the biggest and most important factor in Damian Lillard deciding to return and re-sign with the Trail Blazers,” Charania reported.
On the biggest reason Damian Lillard returned to Portland for @SportsCenter at Night: pic.twitter.com/aQVIl6WIrm
— Shams Charania (@ShamsCharania) July 18, 2025
During his time in Milwaukee, Lillard requested to spend his rehab period near his family outside the city. However, the Bucks reportedly denied that request, which factored into his eventual release and decision to go back home.
Now, with a fresh contract and renewed motivation, Damian Lillard is ready to write the next chapter of his career—right where it all began.
