Blazers News: Former All-Star Claims Portland Has Hurt Damian Lillard's Legacy

Jan 4, 2025; Milwaukee, Wisconsin, USA; Milwaukee Bucks guard Damian Lillard (0) drives for the basket against Portland Trail Blazers forward Toumani Camara (33) in the third quarter at Fiserv Forum. Mandatory Credit: Benny Sieu-Imagn Images | Benny Sieu-Imagn Images

A former NBA star believes the Portland Trail Blazers may have hurt Damian Lillard's legacy.

Following a championship-free two-season stint in Milwaukee that ended with an Achilles tendon tear this spring, the nine-time All-Star point guard recently reconciled with Portland to the tune of a three-year, $41.6 million free agent contract.

The 35-year-old will miss most or even all of the 2025-26 season recuperating. He'll essentially be playing on an expiring deal in 2026-27, as he has a player option for 2027-28. Should Lillard recover his All-Star form, the 6-foot-2 Weber State product could look to earn significantly more money in free agency that summer.

But he's still going to be earning far more than his relatively conservative Portland salary, because Milwaukee opted to stretch and waive the $112.6 million it owes him so that the Bucks can pay him over five seasons, instead of just two.

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To hear former All-Star point guard Gilbert Arenas tell it on his show "Gil's Arena," Lillard deserves far more love than another beloved veteran point guard with significantly more postseason success.

Gilbert Arenas on Dame vs Kyrie:

“If Dame was in a bigger market, we wouldn’t even be having this discussion. Kyrie’s a 3x All-NBA, Dame’s a 7x — that means he was a top 3 guard in the NBA for 7 years.”

(via @GilsArenaShow) pic.twitter.com/OD9Rlvcbfv

— Legion Hoops (@LegionHoops) August 25, 2025

Arenas suggests that, had Lillard playing for a large-market club, he'd have been a bigger deal throughout his prime.

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“If Dame was in a bigger market, we wouldn’t even be having this discussion. Kyrie’s a three-time All-NBA, Dame’s a seven-time — that means he was a top three guard in the NBA for seven years," Arenas said.

Portland is such a small market that the Trail Blazers are the city's only current club among any of the top four American sports. That will be changing soon, however, as Portland will be bringing back the WNBA's Portland Fire as an expansion franchise next spring.

Irving vs Lillard

If one swapped Lillard in for Irving on the more loaded teams the latter played for — the Cleveland Cavaliers, the Boston Celtics, the Brooklyn Nets, and now the Dallas Mavericks — would Lillard have performed better or worse in those situations? Irving has been something of a mercurial personality at times, which has led to some chemistry issues at all his pre-Mavericks stops.

Both are clutch scorers. Irving may have the better handles (for a while, he had the best handles in the NBA, so there's no shame in being a runner-up there), but Lillard had a flair for clutch moments, and generally has had to put his teams on his back in ways Irving has not.

Generally, Irving has played second banana to better Hall of Fame teammates, from LeBron James to Kevin Durant to Luka Doncic. Lillard, though, did seem to have some hierarchical discomfort with LaMarcus Aldridge when they shared the floor together during both players' primes. He was clearly the Scottie Pippen to Giannis Antetokounmpo's Michael Jordan, and their pick-and-roll chemistry was surprisingly spotty.

Both aging veterans are surefire first-ballot Hall of Famers, so ultimately quibbling over accolades is fairly immaterial.

For more news and notes on the Portland Trail Blazers, visit Portland Trail Blazers on SI.