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Damian Lillard’s exile in Milwaukee has come to an end, with the Bucks waiving Lillard two months after he tore his Achilles tendon in a first-round playoff game.
The Bucks, in a surprise move that consumed a full day of the NBA’s annual summer drama, used the stretch provision to spread the remaining $113 million of Lillard’s guaranteed contract over the next five years instead of the next two—and then, with newfound cap flexibility, signed center Myles Turner away from the Indiana Pacers.
Lillard, who turns 35 in mid-July, now becomes a free agent for the first time in his career. But he’s a very unusual one, as he won’t necessarily need to seek a top-tier salary and is almost certain to sit out all of next season while recovering.
Because of these circumstances, news of Lillard’s departure from Milwaukee almost immediately raised the question among fans: Could he return to the Trail Blazers?
If Lillard were to return to the team, ’97 Steve Jobs-style, it would bookend a bizarre saga that saw him spend several purgatorial years reaffirming that he wasn’t going to demand a trade, then signing a supermax contract while the team drafted its next backcourt around him, then ultimately demanding a trade—to Miami and nowhere else—only to watch as his agent was sort of comically outmaneuvered by Blazers GM Joe Cronin, who traded him to Milwaukee for a better package.
According to reporter and longtime Lillard whisperer Chris Haynes, Portland is a potential landing spot, as is Miami. (The Heat no longer have Jimmy Butler or the general allure they did when Lillard asked to be traded two summers ago and the team was fresh off a Finals appearance. But they still have the beach and no income tax.)
For Lillard, the case for Portland is simple. He has a 25,000-square-foot house a few miles away from the team’s practice facility in Tualatin, where he would spend countless hours rehabbing an injury that until a few years ago meant the end of players’ careers. He has three young children who live here. (WW first reported that Lillard and his wife were getting divorced the week after he was traded to Milwaukee.)
If he did return to Portland, it wouldn’t be for money. He would probably be playing on a one-year, veteran minimum contract. Lillard will be making north of $20 million not to play for the Bucks next year, and for four more after that. He’s made $329 million in career salary, and has a lifetime contract with Adidas, which has already paid him about $100 million. He owns a Toyota dealership in McMinnville. In his own words from 2020, in response to a fan suggesting that he might be fined for criticizing referees: “Plenty money.”
The Blazers, for their part, have their own reasons to want to bring Lillard back into the fold. The main premise that the team’s front office is operating under right now is “Scoot Henderson and Shaedon Sharpe become really good.” Sharpe, 22, played his rookie season with Lillard after being drafted No. 7 overall in 2022, while Henderson, 21, was drafted by the team at No. 3 two summers ago, an event that precipitated Lillard’s trade request.
Both guards, though very talented, could use as much tutelage as they can get. A large portion of their developmental windows were shaped by the pandemic, where they were able to train but were robbed of game reps. Sharpe didn’t play college basketball and played only three seasons of high school. Henderson played three seasons of high school and two seasons for the G League Ignite, an ill-fated experiment run by the NBA for a few years that has since been shuttered.
This was presumably a large part of the front office’s thinking in trading for guard Jrue Holiday, one of his generation’s finest perimeter defenders and its most respected teammate. With Holiday, Lillard, and coach Chauncey Billups, Henderson and Sharpe would spend next season surrounded by three guards with a combined 16 All-Star appearances and three championships.
Between the team’s impending sale, its newfound status as one of China’s most popular teams, and the front office’s declaration that next season will be a step forward from four consecutive losing seasons, the coming year appears poised to be among the strangest and most critical in the franchise’s history.
A Lillard homecoming would add to the feeling that all of Rip City is making that journey into the unknown together.
One of the things that made Lillard a special figure was his ability to show that he genuinely cared about Oregon and its people, who regarded him as a hero. He loved us back.
When he left Portland, Lillard wrote, “I do believe a day will come where I put a Blazers uniform on again, and hopefully by then I’ll be forgiven for breaking your hearts along with my own.” That day may come sooner than anybody thought, and we’ll all be better off if it does.
