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DENVER, CO – FEBRUARY 4: Damian Lillard (0) of the Portland Trail Blazers stands on the court after being introduced against the Denver Nuggets before the first quarter on Tuesday, February 4, 2020. (Photo by AAron Ontiveroz/MediaNews Group/The Denver Post via Getty Images)

via Getty
DENVER, CO – FEBRUARY 4: Damian Lillard (0) of the Portland Trail Blazers stands on the court after being introduced against the Denver Nuggets before the first quarter on Tuesday, February 4, 2020. (Photo by AAron Ontiveroz/MediaNews Group/The Denver Post via Getty Images)
Giannis Antetokounmpo is now an NBA champion and Finals MVP with his team, the Milwaukee Bucks. However, it was not an easy task for the Bucks to keep the 2 time MVP. A similar situation has arrived in Portland with Damian Lillard.
When it comes to Giannis, the Bucks made a trade for Jrue Holiday this season. This strengthened the Bucks’ roster and improved their chances of competing. Many believe Milwaukee pulled off this trade to convince Giannis to stay. Likewise, it worked as Giannis signed a 5 year contract extension and also won the NBA title he desired.
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Similarly, Damian Lillard made it clear that he wants to compete, and the Trailblazers are not a competing organisation. Even though he denies a trade request, there is a high chance that it may happen going forward. However, can the Trailblazers pull off a major signing and convince Dame to stay?

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Jun 3, 2021; Portland, Oregon, USA; Portland Trail Blazers guard Damian Lillard (0) drives to the basket against Denver Nuggets forward Michael Porter Jr. (1) in the second half during game six in the first round of the 2021 NBA Playoffs at Moda Center. The Denver Nuggets won the game 126-115. Mandatory Credit: Troy Wayrynen-USA TODAY Sports
McCollum and Ben Simmons trade
Similar to the Milwaukee Bucks, the Trailblazers can add a big name in hopes to keep their superstar. However, they will have to lose out on CJ McCollum.
Portland could potentially trade for Ben Simmons from the Philadelphia 76ers. While Simmons did have a disappointing run in the playoffs, there is no taking away from his abilities. He is an elite defensive guard in the league who can dominate with his size.

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May 26, 2021; Philadelphia, Pennsylvania, USA; Philadelphia 76ers guard Ben Simmons (25) reacts after dunking the ball against the Washington Wizards during the first quarter of game two in the first round of the 2021 NBA Playoffs at Wells Fargo Center. Mandatory Credit: Bill Streicher-USA TODAY Sports
Philly may look to trade Simmons anyway, and they could add a reliable scorer in CJ McCollum alongside Joel Embiid and Tobias Harris. McCollum averaged 23 points on 40% from deep this season.
On the other hand, the Trailblazers receive a major defensive upgrade. Moreover, they could hope that Damian Lillard would be convinced to stay by making their objective clear.
Simmons has been on a tear on the defensive end as he was one of the best defenders in the league this season. Moreover, he is a great playmaker as well. He averaged 1.6 steals and 7 assists this season while putting up 14 points per game. He can be the playmaker to go with Dame and Powell.

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Mar 23, 2021; Portland, Oregon, USA; Portland Trail Blazers guard Damian Lillard (0) dribbles past Brooklyn Nets defenders during the second half at Moda Center. The Brooklyn Nets won the game 116-112. Mandatory Credit: Troy Wayrynen-USA TODAY Sports
Will this convince Damian Lillard to stay?
Dame has no intention of waiting anymore to compete for a title. However, with a trade of Ben Simmons, it still seems like he is developing as a player.
He will need time to blossom into a player who can help Dame win a title. But, Dame has done his waiting and is now desperate to compete. In addition, CJ McCollum is one of Lillard’s closest friends in the NBA. It may not sit well with him if they decide to trade him.

USA Today via Reuters
Mar 28, 2021; Tampa, Florida, USA; Portland Trail Blazers guard Damian Lillard (0) drives past Toronto Raptors forward OG Anunoby (3) during the third quarter at Amalie Arena. Mandatory Credit: Mary Holt-USA TODAY Sports
Even if the Trailblazers do trade him, the main reason remains Damian Lillard’s age. Lillard is now 31, and he is hungry to add a championship to his name.He has given it his all in Portland to try and win. However, they have always fallen short.
Hence, there is still a high chance that Damian Lillard leaves Portland even if they sign a star. He will most likely sign with an organisation that is ready to go all in for a championship.
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Where would you want to see Damian Lillard next season? Let us know in the comments.
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