Should he stay or should he go? This has been the main question surrounding Damian Lillard for years and once again this offseason, the Portland Trail Blazers superstar faces questions about what the future in Portland holds. The Trail Blazers went 33-49 this past season, missing the playoffs for the second consecutive year and Lillard is now 32-years-old.

Time is ticking for the seven-time All-Star and this may very well be the final year for the Blazers to capitalize on having the generational talent, especially since trade talks do seem to be in Dame's mind. When asked recently about the recent trade rumors linking him to other teams, Lillard gave some insight on two teams he'd be willing to join.

“Miami obviously,” Lillard said on Showtime's The Last Stand with Brian Custer. “Miami is the obvious one. Bam [Adebayo] is my dog. Bam is my dog for real. But I mean I think Miami is the obvious one. Brooklyn is another obvious one because Mikal Bridges is my dog too. I mean, both have capable rosters.”

It is definitely no surprise to see the Miami Heat and Brooklyn Nets at the top of Lillard's list, especially given his friendships with the players on those roster. However, there is a catch to all of the Lillard trade talk.

Despite rumors linking him to various organizations and people coming up with hypothetical trades involving him all the time, Dame has yet to actually request a trade from the Trail Blazers! He truly wants to win in Portland, which is why Lillard being on the move this offseason remains unlikely.

The Blazers will need to do everything they can to get their superstar the necessary help to get back to the playoffs during the 2023-24 season, but if he was to request a trade, almost every other team in the league would show interest.

In regards to the Heat and Nets, both may have some trouble putting together an elite-level trade package for Lillard. Currently in the midst of the NBA Finals, Miami is not going to want to part ways with either Jimmy Butler or Bam Adebayo, which leaves Kyle Lowry, Tyler Herro, Duncan Robinson and 2022 first-round pick Nikola Jovic as the Heat's best trade assets.

For the Nets, Mikal Bridges seems like the only untouchable player on their roster, as Spencer Dinwiddie, Dorian Finney-Smith, Royce O'Neal, Cam Thomas and of course Ben Simmons highlight the names of players they could look to package together. Brooklyn also has a handful of tradeable draft picks that could come in handy if they were to make a serious run at Lillard.

Playing the best basketball of his career, Lillard is showing no signs of slowing down and wants to capitalize on his championship-level play. Should Portland continue to struggle and not surround him with capable talents, he could very much request a trade at any point.