“A lot of things are being said,” Lillard said. “It hasn’t come from me. I haven’t made any firm decision on what my future will be, so it’s really no need for anybody else to speak for me.”
The 31-year-old Lillard has spent his entire nine-year career with the Blazers, leading Portland to the playoffs in each of the past eight seasons. In 2019, he signed a four-year, $196 million supermax extension that runs through the 2024-25 season. If Lillard does proceed with a trade request, he would likely emerge as this summer’s most-coveted superstar because of a weak free agency class and Kawhi Leonard’s recent ACL surgery.
Despite his consistent track record of winning and his long-term contract, Lillard has reached a professional crossroads. Since the 2018 death of Blazers owner Paul Allen, an obsessive basketball fan with limitless resources thanks to his Microsoft fortune, the franchise has favored small maneuvers over splashy moves. The Blazers are now owned by Jody Allen, Paul Allen’s sister, who has steadfastly remained behind the scenes.
Blazers General Manager Neil Olshey has chosen not to move guard CJ McCollum and has resisted going all-in for a marquee player via trade, leaving Lillard without an all-star teammate since LaMarcus Aldridge left via free agency after the 2015 season. Persistent injuries to key players have only increased the burden on Lillard, who averaged 28.8 points, 4.2 rebounds and 7.5 assists per game this season. Portland has lost in the first round of the playoffs in four of the past five seasons. The Blazers have reached the Western Conference finals once but gotten no further since Lillard arrived in Portland in 2012.
“[We need to] be more urgent about what our next step is and how we move forward,” Lillard said. “We have a lot of pride about making the playoffs all these years. We’re not a bad team. We’re a winning team.
“But we’ve reached that point where it’s not enough. Do we actually want to win it all? Is that what we’re shooting for? We’ve got to do things to show that. We’ve got to put action behind that desire to win at that level.”
Lillard’s call for assertiveness is understandable given the amount of prominent playoff teams recently boosted by recent trades. The Milwaukee Bucks are in the Finals after acquiring Jrue Holiday, the Phoenix Suns are in the Finals after acquiring Chris Paul and the Brooklyn Nets emerged as title favorites after landing James Harden before falling in the second round having been beset with injuries. The Denver Nuggets, who eliminated the Blazers, acquired Aaron Gordon in a key trade deadline move.
Following the season, Olshey pinned the team’s playoff exit and poor defense on coaching, rather than personnel, and noted that it is difficult for small-market teams to compete for top talent. After the Blazers parted with longtime coach Terry Stotts, Olshey said that starters Lillard, McCollum, Robert Covington and Jusuf Nurkic were all “absolutely” returning for the 2021-22 season.
The Blazers then tabbed Los Angeles Clippers assistant coach Chauncey Billups, a longtime Olshey favorite, as Stotts’s replacement. That hiring prompted substantial backlash from fans and some media because of a sexual assault allegation levied against Billups in 1997.
Lillard, who expressed frustration weeks ago that fans called him out about Billups’s hire, said Friday that a coaching change wasn’t sufficient. Billups, 44, has no previous NBA head coaching experience and spent just one season as a Clippers assistant.
“I don’t disagree that maybe Chauncey can really change our team and make us a better team and get us going in that direction,” Lillard said. “But I think if you look at our team as it is going into next season, I don’t see how you can say, ‘This is a championship team. You just need a new coach.’”
The criticism of Billups’s hiring and questions about the Blazers’ vetting process have further complicated Portland’s summer. While introducing Billups to the Portland media, a Blazers staffer abruptly cut off a question to Billups about the assault allegation. Olshey also refused to divulge specifics about the organization’s background investigation into the incident, which occurred during Billups’s rookie season with the Boston Celtics, saying that such information was “proprietary.”
Subsequent reporting by Oregon Public Broadcasting revealed that the Blazers did not contact Billups’s accuser during their investigation. A Blazers spokesperson later told Willamette Week that the organization had ended an 11-year professional relationship with a private investigator linked to the investigation after it was revealed that he had shared pornographic material on his Twitter account.
Now, the Blazers’ front office must juggle that external pressure with a new round of internal pressure from the team’s franchise player.
“Right now, I’m not sure what I’m going to do,” Lillard said. “What I can say is, my intentions and my heart is set on being in a Trail Blazers uniform for my entire career. But over time, you want to win it all. I want to win it at all in a Trail Blazers uniform, but we all need to be making strides towards that.”