Lillard s return to Portland winners and losers: Bucks save money, the dream of winning the championship team is broken, and Yang Hansen benefits

It's never too late to get home. Damian Lillard proved this.

The 35-year-old star is returning to the Portland Trail Blazers, a progress that is both amazing and feels good, according to ESPN reporter Shams Charania. He signed a three-year, $42 million contract that includes player options for the 2027-28 season and a trade veto. Lillard plans to use the entire 2025-26 season to recover his torn left Achilles tendon before returning to the field in the 2026-27 season.

There are many things to analyze here. What does this mean for the Trail Blazers’ reconstruction? Didn’t they just traded to get Zhu Holiday? And, what should Scudt Henderson do? The rookie’s arrival is basically what forces Lillard to leave the city. Why didn't Lillard join a championship team in the end?

Let us examine the move with one of the best ways we know - analyzing winners and losers - and deal with the consequences of this incurable romantic fanatic dream.

Winner: Damian Lillard

After experiencing a series of huge losses, Lillard won a big victory this time.

First, shortly after he recovered from a thrombosis problem, he suffered a career-changing Achilles tendon injury. The Milwaukee Bucks then cut and extended the payment of $112.6 million for the remaining two years in his contract, giving him free.

A few weeks later, Lillard returned to the team where he started his career and secured absolute control of his future through a trade veto. In addition, he received more money than the Bucks could earn in the next two seasons without sending him away.

This is already a huge victory even before considering the off-field impact. Lillard is a Portland icon. In his return, he will be treated royally. He can also recover closer to the kids, ESPN reporter Shams Charania noted that this has become his top priority.

If you are interested, just look for the negative impact of this contract. Nothing at all—at least for Lillard.

Loser: The NBA championship team that hopes to get Lillard at a lower cost

Many people think that Lillard will join a championship team, even if he won't sign until the middle of the season. The scenario envisioned would be like this: Since the Bucks have paid him, Lillard will sign a 1+1 contract at a low price, return in the 2026 playoffs or early 2026-27 season, and then sign a larger contract in the 2027 offseason after the new team gets the right to birdie.

Of course, the fairy tale assumptions of returning to Portland are always circulating among the crowd, including some emotional factors. But according to Gary Washburn of the Boston Globe, Jason Tatum is an example, who once recruited Lillard for the Boston Celtics.

Specifically, joining the Celtics seems too reasonable. The Celtics are going through a year-long break in the championship, and Tatum is also recovering his torn right Achilles tendon. The duo could have recovered together, returned to the field in the 2026-27 season and continued to pursue the championship. Meanwhile, the Celtics could have made up for some of its rotational squad strength that has been cut — and may continue to cut — due to rising operating costs.

Now this won't happen. Not for the Celtics. Not for any other championship team.

Winner: The Milwaukee Bucks...'s wallet

The Bucks now owed Lillard will be offset by his new contract.

As ESPN salary expert Bobby Max pointed out, the amount offset only applies to the years of his original contract—that is, the next two years. Moreover, this money will not be included in the salary cap until the end of the season.

Nevertheless, the Bucks eventually saved nearly $11.7 million in total, reducing the salary space Lillard occupied from $22.5 million per year (until the 2029-30 season) to about $20.2 million.

Long live (?)!

Loser: The reunion of Scutter Henderson with Lillard does not mean that the team gave up Scutter Henderson. A lot of things can happen between now and the 2026-27 season.

Nevertheless, this adds an extra layer of pressure to the 2023 Tanhua Show, entering its third season. He would have been eligible for an early renewal next summer, and the return of a team icon will be overwhelmed by his head…and his renewal negotiations.

If Henderson's progress is not greater than last year - he seemed to have a better control over the offensive system and his positioning in it - then all kinds of speculation will be rampant. And this doesn't count the pressure he already has. The 21-year-old's move was hard to say as a recognition for the 21-year-old. The two can play together, but Henderson has been on the bench for most of his career. His path as a long-term starter and taking control of the team has become more blurred.

Do we have to believe that the Trail Blazers’ plan is to let Holiday or Lillard play a substitute behind Henderson in the 2026-27 season?

Winners: Yang Hansen and Donovan Klingen

I mean:

More serious, the Trail Blazers had a hard time helping their inside players last season, and they wouldn't be able to help Yang Hansen (to be honest, he probably didn't need it) or Donovan Klingen next season. But Lillard's return in 2026-27 ensures that they will have a player that is attractive enough to provide them with extra space on the court and can make a more comprehensive pass judgment than anyone in the current roster.

If Henderson breaks out in the third season, Deni Avdia continues to improve, or the Trail Blazers introduce another playmaker from now until the 2026-27 season, then this is not such a big victory. But it is important no matter how the Trail Blazers improve their (two major) insiders' survival on the offensive end in the future.

Other winners, losers and pendingrs

Putted: Shetton Sharp

Sharp is now eligible for his rookie early contract renewal, and many uncertainties about Henderson's future are also related to him. Intuitively, the 22-year-old is more in line with Lillard's partner because he is not a point guard. But including these two players, plus Henderson and the new Ju Holiday, the Trail Blazers' backcourt has become crowded again.

Winner... Also losers (?): Ju Holiday

Speaking of Holiday, with Lillard returning to the team now, it feels like he was traded before the 2026-27 season has become a foregone conclusion. Maybe he would be happy for the chance to play elsewhere. Maybe he'll be frustrated by being traded again — especially if that happens in the middle of the season. Or maybe the result is that the Trail Blazers are unable to find a takeover for the 35-year-old’s remaining contract ($104.4 million for three years), and if he stays, he will either be ecstatic or feel frustrated.

Winner: Rebuilding the team for the 2026-27 season in case someone is uncertain whether the Trail Blazers will accelerate the reconstruction after getting Holiday, and now we know they plan to press the acceleration button at the latest next summer. This is great news for any team that wants to play with the smallest obstacles.

Loser: The 2025 free agent

Trail Blazers are unlikely to pay for anyone other than Lillard, but really spending that money puts them out of the fight for any remaining free agents in the market. If any remaining restricted free agents (such as Quentin Grimes and Cameron Thomas) are under extreme pressure and perhaps hoped that the Trail Blazers would throw out a middle-class offer contract, that would have become impossible.

Author: Dan Favale

Translator: GWayNe