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Portland Trail Blazers star Damian Lillard signed a contract extension with the organization that will keep him on the team through the 2026-27 season. But at least one former player questioned it.

J.R. Smith, a two-time NBA champion who last played for the Los Angeles Lakers during the coronavirus-impacted 2019-20 season, wondered whether Lillard was making the right move to stick it out with the team that drafted him instead of going to chase an NBA championship with a different team.

"Like, I love Dame. I love his game. I respect him for doing what he's doing. But at the same time, it's like, you just going to rot in Portland, bro? You are unbelievable." Smith said.

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Damian Lillard watches a game in March 2022

Damian Lillard of the Portland Trail Blazers watches play during a game against the Oklahoma City Thunder at the Moda Center on March 28, 2022, in Portland, Oregon. (Abbie Parr/Getty Images)

The one-time NBA Sixth Man of the Year made the remarks for an upcoming episode of "No Chill with Gilbert Arenas" on the Fubo Sports Network.

Arenas said if he could win six rings in his first six years, he would go for it. The former NBA star added that the lack of rings would hurt the conversation around Lillard’s legacy in the NBA when it’s all said and done.

"The people you put in front of me are not even close to my stature, but because they got a ring, they get pushed in front of me," the former Washington Wizards star said.

Damian Lillard drives on the Nuggets

Portland Trail Blazers guard Damian Lillard (0) drives to the basket against Denver Nuggets guard Markus Howard during the second half of Game 5 of a first-round NBA playoff series, June 1, 2021, in Denver. (AP Photo/Jack Dempsey)

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Lillard is one of the best players in the NBA.

Portland selected Lillard with the No. 6 pick of the 2012 draft. He was an All-Star by his second year. He signed a four-year, $176.2 million deal in 2019 and then a two-year, $121.7 million extension in July.

Lillard is averaging 24.6 points, 6.6 assists and 4.2 rebounds in 711 career games. Portland hasn’t made it past the Western Conference Finals since Lillard became the centerpiece of the organization.

Damian Lillard against the Hornets

Portland Trail Blazers guard Damian Lillard, left, shoots over Charlotte Hornets guard LaMelo Ball during the second half of a game in Portland, Oregon, on Dec. 17, 2021. (AP Photo/Craig Mitchelldyer)

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Portland only has one championship in franchise history — coming in 1977 with Maurice Lucas and Bill Walton leading the charge.