Milwaukee Bucks guard Damian Lillard hasn’t had the season anyone expected.

Though named an All-Star for the eighth time in his career, it hasn’t quite felt like it’s been that type of performance. The production is there, with Lillard averaging 24.3 points and 7.0 assists per game in the regular season. After the Bucks brought in head coach Doc Rivers, Lillard found greater comfort in the offense. After the All-Star Break, the 33-year-old shot 38.3 percent from 3.

However, Lillard’s been as up-and-down as his sub-.430 field goal percentage suggests.

Damian Lillard Speaks Out Against Latest ESPN Report

Acquired by the Bucks in their effort to appease Giannis Antetokounmpo, Lillard seems more like a marquee player Milwaukee was happy to luck into rather than one whose fit they thought all the way through. A team that had relied on well-rounded point guards like Eric Bledsoe and Jrue Holiday prior to Lillard’s arrival, the Bucks are less balanced than in years past.

From the 2020-21 to 2022-23 seasons, Milwaukee had a top-10 offensive rating or defensive rating twice. This season, the Bucks have the sixth-best offensive rating (118.4) but rank 19th in defensive rating (115.8). The last time Milwaukee’s defensive rating ranked in the bottom half of the league was 2017-18.

With Lillard under contract through the 2026-27 season, the Bucks have three distinct options:

One, they could cut him loose this offseason, perhaps trading him to his preferred destination in exchange for Miami Heat guard Terry Rozier. Such a deal seems like it would be best for both sides.

Secondly, Milwaukee could run it back with Lillard next season, at least until the trade deadline. This allows the Bucks to see if he and Antetokounmpo can lead Milwaukee to a championship as well as if they can gel together on and off the court.

Lastly, they could ride it out with Lillard for a few more seasons. A highly decorated and successful player with superior scoring ability, there aren’t many backcourt players as valuable as he is.

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However, whatever they decide, they have to make sure he wants to be there even now.

Up to this point, there’s been a question of whether he’s happy in Milwaukee. Working through a strenuous divorce and separated from his children, Lillard is understandably strained by personal matters. Yet, he also seems to be at a loss of what to do in Milwaukee with his free time. To that point, it’s hard to imagine that he would have that same issue in Miami.

When factoring in the drama of a midseason head coaching change and a 17-19 record under Rivers, there’s even more of a cause for concern. The situation has even gotten to Antetokounmpo.

Despite all of the hoopla suggesting that he’s dissatisfied in Milwaukee, Lillard is attempting to dispel that notion:

“You know, like I saw somebody say ‘Dame is not happy in Milwaukee’ or something like that,” Lillard says, responding to a recent diatribe by ESPN pundit Stephen A. Smith. “…I love the situation that I’m in. I also know what I have going on outside of basketball going on that kind of drains me at times.

Miami or L.A.?

Lillard’s words sound good but his actions in the offseason will show where his mind is at.

There’s no doubt that Lillard appreciates being in a position to compete for a championship. After all, Lillard hasn’t been in the playoffs since 2021 and has never made it past the Western Conference Finals. The one time he had the Portland Trail Blazers did make it to the Conference Finals, they were swept by the Golden State Warriors.

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Nonetheless, the Bucks aren’t the only championship contender out there.

If there’s another one that could provide him with better work-life balance, he may quietly request a trade. The Heat are one team that seems to fit this criteria but the Los Angeles Lakers may as well. The California native can the same lifestyle in Hollywood Beach as he does in South Beach.

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