Before the blockbuster trade to the Milwaukee Bucks, Damian Lillard spent nearly a decade trying to build a championship contender in the Portland Trail Blazers. While the team became one of the better teams in the Western conference in that span, the Blazers had only ever reached the Conference Finals in 2019. They ran into Kevin Durant and the Golden State Warriors, who swept them as their dynasty was already on its last legs. After settling with his new team, Damian Lillard ponders whether he and All-Star LaMarcus Aldridge could have brought a ring to Portland.
Recently, Dame appeared on the Club 520 podcast with Jeff Teague, where they had a conversation about all things NBA.
“One thing I think about in my career is like, ‘If he woulda never went to San Antonio, we woulda won at least once already,” he said in response to a question about playing with the seven-time All-Star.
Dame Time before the Bucks
In 2015, LaMarcus Aldridge signed with the Spurs as a free agent, where he contributed to their playoff squads until injuries slowed him down. Then, in 2021, LA joined the Brooklyn Nets who became title favorites after forming a Big Three of Kevin Durant, Kyrie Irving, and James Harden. However, an irregular heartbeat diagnosis eventually forced him to hang up his sneakers for good.
What did Damian Lillard think would have happened if LaMarcus Aldridge stayed with the Blazers?
“I woulda came into my own, but he was that good,” he said. “He was that good.”
On the other hand, Lillard also did his part in leading the Blazers into the playoffs during his entire tenure there. He'd also made memorable moments, such as the buzzer-beating threes to eliminate the Houston Rockets in 2014 and the Oklahoma City Thunder in 2018. The second game-winner was even harder than the first one, a 37-foot heave over Russell Westbrook that capped off their rivalry.
Even after the Blazers had fallen from the standings, they still made the playoffs in the Orlando bubble as the eighth seed against the first-seed Los Angeles Lakers. After winning Game 1, the Blazers became the “best eighth seed of all time” until the Lakers won four straight games to send them packing.
The last time Lillard led the team to the playoffs was against the Denver Nuggets in 2021, where they went home in six games during the first round. During that series, he also set a playoff record of 12 made three-pointers in the double-overtime classic Game 5.
Can Damian Lillard finally win a ring?
As the Blazers finally decided to rebuild, though, they sent Dame to the Bucks, his best chance to win his first NBA ring with Giannis Antetokounmpo. Despite the Bucks' playoff flameout last season, Damian Lillard still has a better chance to win a title in a relatively weaker Eastern conference. However, it still remains to be seen whether Lillard's years of grinding with his former team will finally pay off in June.
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