For years, many have speculated that Damian Lillard should leave the Portland Trail Blazers. Time and time again though, the seven-time All-Star has proven his allegiance to his franchise.

Now through 11 seasons with the Trail Blazers, Lillard is currently in the prime of his career and questions about his future continue to surface. Portland is not the contending threat it once looked to be after missing the postseason for the second consecutive year, and the 32-year-old has hinted at his frustrations with the organization.

Lillard could very much be nearing his breaking point with the Blazers and should he request a trade, the Brooklyn Nets seem to be a possible suitor for the seven-time All-Star.

Not only is Lillard close friends with Nets' breakout star Mikal Bridges, but he was in attendance for Game 3 of Brooklyn's first-round series against the Philadelphia 76ers.

So many have been asking if a trade involving Lillard between the Blazers and Nets could actually happen this upcoming offseason, and the short answer is “yes.”

However, this question is a lot more complicated than a simple “yes or no,” as a lot goes into a potential trade for Lillard. Not to mention, the league's new Collective Bargaining Agreement (CBA) also factors into both teams' decision to make a trade of this proportion.

For starters, Lillard has two more years left on his contract and is set to make $45.6 million during the 2023-24 season and about $48.8 million during the 2024-25 season. Despite the departures of Kevin Durant and Kyrie Irving this season, the Nets still remain one of the league's highest-paying teams, which will result in some penalties under the new CBA.

After how things played out with Durant and Irving over the last few seasons, Brooklyn may be very skeptical of bringing in yet another superstar talent on the back-half of their career. On the other side of things, though, players like Lillard do not come available often, which is why capitalizing on a potential move this offseason could instantly thrust the Nets back into the championship equation in the Eastern Conference.

Financially speaking, the Nets can get a deal done if they are willing to remain above the salary cap for the 2023-24 season and beyond, as Lillard would be much more for this franchise than just a two-year rental. Who and what Brooklyn would trade away, though, becomes the most important question here.

Assuming Bridges is “untouchable” in trade talks for the Nets, as he should be given the breakout season he had, the only other plausible way for this deal to have traction is if Ben Simmons is involved. Simmons' time in Brooklyn has been overshadowed by injuries, and getting a fresh start on a younger, rebuilding team could be exactly what he needs to revitalize his career.

Trading Simmons is not as easy as it may be in NBA 2K on your PlayStation or Xbox. The former No. 1 overall pick comes with a ton of baggage and question marks not only about his health, but his willingness to play. If Portland does decide to rebuild and ship Lillard somewhere, bringing back Simmons may not be too appealing to the Blazers.

From the Nets' perspective. though, moving Simmons makes a deal for Lillard a lot easier, as he is set to make $37.9 million during the 2023-24 season, followed by $40.3 million during the 2024-25 season. Getting off his contract would be ideal for Brooklyn and makes matching Lillard's incoming salary a lot easier.

The bottom line in a potential trade with the Trail Blazers is that the Nets must be willing to give up considerable assets. If Bridges isn't going to be on the move, players like Cam Johnson, Cam Thomas and Day'Ron Sharpe may have to be shipped out.

Johnson is set to be a free agent this offseason, which could complicate things if he was to be involved in trade talks. The chances of Johnson leaving in free agency are also low, as he seems like a perfect fit on the wing in Brooklyn.

Thomas is a very intriguing name that could instantly be a key talent for any rebuilding team in this league. The former first-round pick is an electric scorer and proved that with the Nets this season, averaging 20.8 points over 25 games in which he played at least 20 minutes. Thomas even recorded three straight 40-point games in February.

Packaging Simmons, Thomas and Sharpe together creates about $42.3 million in outgoing salaries, and it is certainly possible the Nets would need to include another player such as Spencer Dinwiddie or Dorian Finney-Smith. Such a move, though, would likely require a third team to be involved to take on that player in exchange for a draft pick going back to Portland.

Along with the three players listed above, the Nets would also have to be willing to deal a lot of the first-round picks they have, most of which come from the Suns as part of the Durant trade.

From the Brooklyn's perspective, a trade involving Damian Lillard could absolutely happen in a deal revolving around Ben Simmons, Cam Thomas, Day'Ron Sharpe and at least three first-round picks. From the Blazers' perspective, though, it is hard to imagine they would be blown away by this proposal.

Thomas is a nice building block for Portland to get back, but the front office would much rather acquires a real building block like Bridges for obvious reasons. If they are giving up one of the best players in the league right now in Lillard, the Blazers will be expecting quite the haul in return, something Brooklyn may not be able to supply them with at this time.