When Damian Lillard’s Achilles tendon ruptured on April 27, his career teetered on uncertainty. Speculation surrounded the Milwaukee Bucks, raising concerns about the future of their star player, Giannis Antetokounmpo, and Lillard’s potential trade away from the team.

Just 81 days later, Lillard stands out as one of the offseason’s biggest winners. The Bucks opted to waive Lillard, providing him with the freedom to choose his destination. As an unrestricted free agent for the first time, he made the momentous decision to return home, agreeing to a three-year, $42 million deal with the Portland Trail Blazers, as reported by ESPN’s Shams Charania.

“RipCityyyyyyyyyyyyyyyyy!!!!!!!!! @trailblazers pic.twitter.com/x3jnZr1s0G” — Damian Lillard (@Dame_Lillard) July 17, 2025

Lillard is set to receive $14.1 million from the Blazers next season, despite not playing due to his injury. He planned to undergo rehabilitation in Portland to stay close to his family. Notably, Lillard has a no-trade clause in his new contract, ensuring that any future decisions remain in his control.

Should he excel upon his return, he has the option to hit the free agency market in the summer of 2027, akin to what would have happened had the Bucks retained him. Meanwhile, Milwaukee is committed to paying him $22.5 million annually over the next five years.

The Blazers’ investment in Lillard amidst a budding backcourt featuring young players like Scoot Henderson and Shaedon Sharpe raises questions about their strategic approach. However, the reunion appears beneficial for Lillard, as it grants him the arrangement he sought, complete with a no-trade clause and the opportunity to recover comfortably in his home city.

Ultimately, while Lillard cannot erase the past struggles, his return to Portland symbolizes a pivotal redo in his career.