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The Clock Is Ticking On Damian Lillard's Future With Trail Blazers

After constantly downplaying the talk of him leaving the Portland Trail Blazers through the years, this offseason may finally be the time Damian Lillard looks to continue his career elsewhere.

“For me, my heart is Portland Trail Blazer.”

This was what Damian Lillard said near the end of the 2021-22 season and the All-Star guard committed to the Portland Trail Blazers with a new extension this past offseason, keeping him under contract through the 2024-25 season.

After another failed season and the direction of the franchise being unknown though, Lillard’s future with Portland is once again going to be one of the key talking points of the upcoming NBA offseason.

Very few played in the league have been able to achieve what Lillard has done through the years and while he played in just 58 games this season due to various injuries, the Blazers star still managed to average 32.2 points, 7.3 assists and 4.8 rebounds per game while shooting 46.3 percent from the floor and 37.1 percent from three-point range.

Damian Lillard continues to be one of the most dynamic offensive players in this league and at 32-years-old, he is currently at the peak of his career.

The last 11 seasons for Lillard have been filled with highs and lows and while Portland did go to the playoffs eight straight times from 2014-2021, including a trip to the Western Conference Finals in 2019, the Trail Blazers as an organization have consistently been taking steps backwards.

Missing the playoffs for the second consecutive season for the first time in just about a decade, a rebuild could very well be on the horizon for Portland, but Damian Lillard may not be a part of it this time.

“Not only will I have the decision to make, but I think the organization will too,” Lillard recently said when talking with ESPN’s Stephen A. Smith during Wednesday night’s play-in games. “Are you gonna go young or are we gonna get something done. I think we just have to be fully committed to either one. I just think we at that point now where everybody wants to win and they believe I deserve that opportunity.”

Following Portland’s final game of the regular season, Lillard also told reporters that he “doesn’t have much of an appetite for building with guys two and three years away” and that he wants to play to win right now, according to Sean Highkin of the Rose Garden Report.

While he has not gone out and said that he wants to be traded, Damian Lillard is clearly sending a message to the Trail Blazers’ front-office that he wants to win and be on a team that has a chance to compete at the highest level possible. This was his message a season ago and it was not well-received, which is why the All-Star is once again clearly sending his wishes.

If the Trail Blazers decide that they are not ready to go “all-in” and make championship-like moves, instead focusing on their future and developing their youth, it is not hard to believe that Lillard will request a trade this offseason, becoming one of the biggest names to ever hit the trade market.

Having two years and about $95 million left on his contract, it would be very hard for a vast majority of the teams around the league to go after Lillard, especially with the changes coming in the new collective bargaining agreement, but there are still a handful of suitors who would be willing to relinquish a lot for him.

The Miami Heat are an obvious team that would be willing to give up anyone other than Jimmy Butler and Bam Adebayo in initial trade talks for Damian Lillard, the Philadelphia 76ers could turn their attention to Lillard in the event that James Harden decides to leave in free agency and it is possible that other teams like the New York Knicks, Brooklyn Nets, Toronto Raptors and Los Angeles Lakers would come up as potential suitors should Lillard request a trade.

As far as Lillard wanting out of Portland and seeking a new team in the offseason, there is a growing belief around the league that this will ultimately happen with the All-Star point guard.

“Dame has given everything to Portland, he’s stuck with them all of these years, and yet they continue to waste the prime of his career,” one Eastern Conference executive told Fastbreak on FanNation. “That organization clearly wants to take a step back and rethink what their long-term plan is and for Lillard, I don’t see how that fits his agenda. He will not be able to accomplish what he wants to and what he is capable of doing in this league with that team.”

Finishing with the fifth-worst record in the NBA this season, the NBA Draft Lottery could be very telling as to what the future holds for the Trail Blazers.

They have a 10.5 percent chance of landing the top overall pick in the 2023 NBA Draft and should they do so, bringing in Victor Wembanyama may very well kick-start a snowball effect of moves and trades for the Trail Blazers to make.

If Wembanyama is not coming to Portland though and they end up with the fourth, fifth, sixth or seventh pick instead, the question for the Blazers becomes whether or not they would do what Lillard wants in terms of dealing the pick for added “win-now” help or keep the pick, rebuild and end up trading Lillard as part of their rebuild.

So many question marks surrounding the Portland Trail Blazers and what the future holds for Damian Lillard, which is why they could very well control the market this upcoming offseason. 


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