Blazers, Damian Lillard Had Multiple Meetings Leading Up to $42 Million Deal

The Portland Trail Blazers ended up surprising the NBA world by signing Damian Lillard to bring him back. No one had them on their radar when it comes to Lillard signing somewhere.

After being waived by the Milwaukee Bucks, Lillard was a free agent for the first time in his career. He had a lot of options to sign with teams who could contend for a championship in the next couple of years.

Instead, he decided to come home to Portland. The Trail Blazers are certainly happy to have him home. He signed a three-year deal with the Blazers to return to the franchise after many meetings with the team.

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According to ESPN's Shams Charania, the Blazers and Lillard met multiple times as they were negotiating a deal.

Lillard and the Trail Blazers both deeply cared about the comeback in recent weeks – with multiple meetings among the Portland franchise icon, general manager Joe Cronin and head coach Chauncey Billups to bond together and move forward united on a new deal. https://t.co/Ki8HTaQth6
— Shams Charania (@ShamsCharania) July 17, 2025

Lillard wanted to clear the air with general manager Joe Cronin before deciding to sign back with the Trail Blazers, as well.

Portland GM Joe Cronin met at the star’s house weeks ago and the two made amends and focused their attention on getting a deal done to give Lillard the opportunity to retire as a Trail Blazer. https://t.co/h4XNp555W3
— Chris Haynes (@ChrisBHaynes) July 17, 2025

The Blazers are happy to have him back, even if he won't play at all next season. He will play again for the Blazers in the 2026-27 season, which could be a year that the Trail Blazers try to add some veteran players to make a run.

Next season will be about the development of the young players on the roster around Lillard. Besides Lillard, Jrue Holiday is the oldest player on the roster.

Holiday will be looked at as a veteran presence for next year on a team that doesn't know what it takes to win. He will be instrumental for a group that has playoff aspirations next year.

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Lillard was clearly pleased with what he heard from Cronin in their meetings. He also must like what the roster has to offer in what will be the final years of his career.

Signing in Portland is an indication that he doesn't believe winning a championship is the most important thing to him anymore. He wants to be near his kids and his family, and that's all that he cares about.

This past season with the Bucks, Lillard averaged 24.9 points, 4.7 rebounds, and 7.1 assists per game.

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For more news and notes on the Portland Trail Blazers, visit Portland Trail Blazers on SI.