Damian Lillard reportedly finalizing $42m, 3-year deal to return to Trail Blazers

Damian Lillard is heading back to where it all began. The nine-time All-Star is reportedly putting the finishing touches on a three-year, $42 million deal with the Portland Trail Blazers — the franchise he called home for the first 11 seasons of his NBA journey, according to NBA Insider Shams Charania. The contract includes a player option for the 2027–28 campaign and features a no-trade clause, giving Lillard significant control over his future.

The 35-year-old guard, who just celebrated his birthday this week, was waived by the Milwaukee Bucks on July 7. The move allowed the Bucks to stretch the remaining $113 million left on his contract, clearing the financial runway to sign free-agent center Myles Turner.

Lillard isn’t expected to suit up at all during the 2025–26 season as he recovers from surgery to repair a torn left Achilles tendon — an injury he sustained on April 27 during Game 4 of Milwaukee’s first-round playoff exit against Indiana. That game marked just his third appearance since returning from a blood clot in his right calf that sidelined him for a month. He also missed the Bucks' final 14 regular-season contests due to the same issue.

Despite receiving overtures from playoff-caliber teams offering mid-level and veteran-minimum contracts, Damian Lillard has opted for a homecoming instead. The star guard is returning to Portland, where his family is rooted, prioritizing stability and familiarity over chasing titles elsewhere.

In recent weeks, conversations between Lillard, Blazers GM Joe Cronin, and head coach Chauncey Billups gained serious traction, with all sides eager to make the reunion happen. His longtime agent Aaron Goodwin is currently ironing out the final contract details.

Thanks to a combination of his stretched Milwaukee payout and his new deal in Portland, Lillard is expected to rake in $70 million next season and a staggering $141 million over the next two years.

The journey back to Rip City comes full circle after Lillard requested a trade in 2023 when Portland leaned into a youth-driven rebuild. He was sent to Milwaukee in a three-team blockbuster that included Jrue Holiday and Toumani Camara heading to the Blazers. Holiday was later flipped to Boston, but has since been reacquired by Portland this summer.

Now, the Trail Blazers find themselves with a rejuvenated core led by Lillard and Holiday, along with Robert Williams III, Scoot Henderson, Camara, and a healthy stash of future draft capital, including a 2029 first-rounder and a pair of Bucks pick swaps.

Lillard, who posted 24.9 points, 7.1 assists, and 4.7 rebounds in 58 games with Milwaukee last season, owns career averages of 25.1 points, 6.7 assists, and 4.3 boards across 900 games.

Although he'll spend the 2025–26 season rehabbing his surgically repaired Achilles, returning to the city where his children are being raised and the franchise that helped define his career outweighed all other options.

In the trade fallout from Lillard's original move to Milwaukee, Portland landed Holiday, Camara, and assets that later turned into Robert Williams, Malcolm Brogdon, and Deni Avdija. With Lillard and Holiday now reunited in the Pacific Northwest, Portland's rebuild looks more like a retool, especially after finishing last season on a 22–18 tear, anchored by a defense that ranked top five overall and third in transition stops during that stretch.