Frankly, the answer to the question was obvious from the very moment C.J. McCollum's breakout third season led the most optimistic Portland fans to ponder it. No, a team led by he and Damian Lillard won't ever win the Trail Blazers their first championship since 1977.
The reasons why vary, and indeed have much to do with the fact that the last champion to be built around a pair of small guards won the title over 30 years ago. Isiah Thomas and Joe Dumars weren't just a Hall-of-Fame backcourt, but surrounded by the most notorious defense in league history. Lillard and McCollum's supporting casts have never exactly resembled those Thomas and Dumars enjoyed with the "Bad Boys" Detroit Pistons.
But at least Portland once had the financial flexibility needed to put a team around Lillard and McCollum that could theoretically compete with the league's best. The problem is the Blazers never reached that ceiling, their 2019 Western Conference Finals appearance far more the result of shoddy competition than their real standing among basketball's elite.
A sweep at hand of the Golden State Warriors, playing without Kevin Durant, only further confirmed what initial skeptics of the Lillard-McCollum pairing never doubted. Definitely not among them? Portland president of basketball operations Neil Olshey, who reacted to the Blazers advancing within a round of the Finals in a self-serving vacuum devoid of context and objectivity.
Lillard, clearly, earned the four-year maximum extension he signed with Portland in wake of the Blazers being eliminated by Golden State. Anyone suggesting McCollum wasn't worth his subsequent three-year, $100 million extension was immediately referred to his 37-point masterpiece in a Game 7 road win just six weeks earlier—the victory that sent Portland to its first Conference Finals since the millennium.
McCollum's epic performance against the Denver Nuggets under do-or-die stakes is a hazy memory now, clouded by his comparative no-show in the first round of this season's playoffs versus the very same team absent Jamal Murray and Will Barton.
Portland's dispiriting loss was far bigger than McCollum's individual struggles, of course, to which Lillard alluded after the Blazers were eliminated in Game 6. His loyalty to Rip City wasn't necessarily wavering.
But Lillard made clear Portland's longtime comfort with the status quo of wide-eyed championship aspirations followed by postseason flameouts was no longer going to cut it.
"Obviously, where we are isn't good enough to win the championship if it's not good enough for us to get out of a first-round series with two of their best three or four players not on the floor," he said.
Terry Stotts was gone less than 24 hours later, an expected first step in the Blazers' anticipated offseason overhaul.
At his season-ending presser, a few days after parting with a coach who'd guided Portland to the league's longest active playoff streak, though, Olshey insisted that the Blazers' roster wasn't the problem.
Whoever succeeded Stotts would evidently need to make do with a foundation of core players that had proven yet again it wasn't capable of legitimate title contention.
"At least they know what they're dealing with for the most part in terms of how do they get this group to get to another level on the defensive end of the floor," he said of prospective coaching candidates. "And that will clearly be critical in anybody advancing in the process, is they're gonna have to prove they're gonna have the ability to do that – in much the same way some of the coaching hires from last summer were able to do it – without a lot of personnel changes."
Olshey deemed McCollum untouchable in trade talks that could have brought Paul George to Portland in the summer of 2017. He was even reportedly hesitant to make McCollum available in a potential deal for James Harden last winter.
It could have been easy to give Olshey some benefit of the doubt for suggesting the Blazers would mostly stand pat this summer.
McCollum might be a negative value on his current deal, which only kicks in next season. Allotting nearly 30 percent of the salary cap for multiple seasons to an off-guard without positional versatility on defense would be a tough sell on the trade market, even if McCollum was five years younger. But he turns 30 in September, and suffered small fractures in both his vertebrae and foot in the last calendar year.
McCollum's trade value is very much a matter of debate, but certainly lower than it's ever been. While Olshey's responsibility for that development is obvious, at least an indirect acknowledgment of the Blazers working from a position of weakness they created would have lent him some credibility.
But rather than allowing for the mere possibility of his mistakes contributing to Portland's crossroads, Olshey acted as if they didn't exist entirely, laying most blame at a highly respected outgoing coaching staff. Local media apparently warranted some scorn, too.
Whoever's it was, Culpability definitely wasn't Olshey's—just like his palpable silence has made sure that remains the case while the Blazers face backlash for agreeing to terms with Chauncey Billups as the team's next head coach. Instead of Olshey's preferred scapegoat getting the criticism he deserves, though, it's been the person in the organization most responsible for him keeping his job.
Yahoo Sports' Chris Haynes reported on Sunday that Lillard "may" soon break on his longtime pledge to play his entire career in Portland. Why? Lillard's sense that Blazers fans are "attacking him" for Portland's decision to hire Billups, who in 1997 was accused of sexual assault. "Concerns" about the team's ability to put a title-worthy roster around him also reportedly play into Lillard's suddenly uncertain future.
Lillard, to be clear, isn't completely absolved of the controversy surrounding Billups. Yahoo reported that he "played no part in consummating" the Blazers' choice of Billups, conveniently ignoring that Lillard threw public support behind Billups and Jason Kidd in the immediate aftermath of Stotts' departure.
Responding to the criticism on Saturday, Lillard insisted he simply named two of the candidates he'd "heard" might be available when asked for his opinion. There was no ultimatum that Portland had to hire his preferred coaches.
Lillard said he was initially unaware of the allegations made against Billups and Kidd's history of spousal abuse, too.
The sourced refutation of Lillard playing a role in Billups' pending hire rings hollow. His support for Billups is literally on the record, and ESPN reported that their strong existing relationship played a factor in the 2004 NBA Finals MVP being offered the job. Lillard and Billups even "talked frequently throughout the process," per ESPN.
Still, it's safe to say Billups is more Olshey's choice than Lillard's. Olshey claimed Billups off waivers in 2011 when he was leading the LA Clippers' front office, and spoke in absolute fawning terms of the five-time All-Star basketball acumen and natural leadership abilities over ensuing years.
While reporting Billups as the last coach standing in Portland's three-week search, ESPN put Olshey's affinity for him best.
Olshey has long considered Billups one of the best leaders he has ever encountered in the NBA.
Owner Jody Allen, remember, reportedly hoped to hire Becky Hammon. Olshey even confirmed Lillard's account of him casually naming Kidd and Billups during that inflammatory presser, insisting the buck stopped with the front office in deciding the Blazers' new coach.
"I called Dame to let him know we were making a coaching change, kinda told him the model for what we were looking at in terms of profile, the kind of candidates we'd be looking at," Olshey said. "And I said, 'Hey, if you have any names let me know,' and he gave me a couple of names."
Olshey got his guy, basically. Lillard, it appears, just happened to approve of Billups as well.
Left to interpretation is whether Lillard would have suggested Billups if he'd known about the allegations against him. That Lillard is broaching leaving Portland after learning of and receiving backlash for them seems pretty telling.
But what's not even worth wondering is the possibility that Lillard is lying about not being privy to them previously. He's a symptom of the NBA family's systemic blind eye to violence against women regardless.
Billups played for six different teams after he was traded from the Boston Celtics on February 18, 1998, about three months after being accused of rape. He spent a half-decade of his post-playing career as a prominent part of ESPN's coverage team, then joined the Clippers as a television analyst in 2019 before moving over to Ty Lue's bench as an assistant this season.
Billups has been vetted over and over and over by league entities throughout his career, and Portland reportedly conducted its own "internal investigation" of the claims against him. How many, if any, of those probes included conversations with Billups' alleged victim is unknown.
But all of them ostensibly found that his story—the same one Billups has been telling for more than 20 years—aligned with verifiable facts of the night in question, whatever investigators deemed those are.
- Details of the reported rape can be found HERE (CONTENT WARNING).
Billups denies engaging in any non-consensual sex acts with his purported victim, and was never charged with a crime. He settled a civil suit filed against him three years after the incident.
Kidd, meanwhile, pleaded guilty to spousal abuse in 2001 after striking his then-wife, an extremely visible presence at Phoenix Suns games during their time together. He was dealt to the New Jersey Nets the following offseason, Suns owner Jerry Colangelo barely concealing that Kidd's history of abuse factored into their decision to trade him.
Kidd finished second in MVP voting the next season, leading the New Jersey Nets to the 2002 NBA Finals. He'd later win a championship with the Dallas Mavericks and spark the New York Knicks' brief resurgence, universally championed across the league for his veteran guile. Neither of his drama-filled tenures as coach of the Brooklyn Nets nor Milwaukee Bucks had anything to do with Kidd's abhorrent past.
When the Mavericks, who three years ago committed to addressing a toxic workplace culture that included accounts of sexual harassment, hired Kidd as the team's head coach last week, he was subject to congratulatory notes from all corners of the NBA.
LeBron James doesn't normally go out of his way to stan for assistant coaches on social media.
Again, Kidd pleaded guilty. He and his team at the time addressed his pattern of physical abuse in multiple public forums. It was the catalyst that helped him reach an even higher plane of achievement and respect from playing peers, coaches, analysts and fans alike with the Nets.
Kidd's violence was anything but unknown, yet he's still revered by the vast majority of league circles. Rick Carlisle, head of the coach's union, even publicly lobbied for Kidd to replace him with the Mavericks, sarcasm or not.
Lillard should've known about Kidd's past. There's no excuse otherwise. But it's indicative of just how willing the NBA is to overlook abuse against women—at least when the right player is accused—that Lillard could plausibly profess ignorance of Kidd's transgressions.
Olshey definitely knew about them. He suggested as much while castigating Lillard for going public with his approval of Kidd and Billups, saying their names being floated "certainly didn't serve them well in the ensuing 48 hours"—a reference to outcries from Blazers fans about the notion of Kidd taking over in Rip City.
Of course, Olshey was no doubt aware of allegations about Billups, too.
Maybe you disagree that an accusation of rape should disqualify a candidate from one of the 30 most sought-after and visible coaching jobs on earth. Olshey does.
But where everyone litigating this untenable situation should find common ground is that it's not on Lillard—much as fans have come to expect all forms of leadership from him—to be the arbiter of sexual assault claims against his future coach.
The league has spent years shaping the world of indifference to violence against women in which Lillard lives. It's disappointing he didn't step outside of it by himself, and more so that his response to being pressed to do so seems too big an ask of him—let alone could lead to a potential trade request.
That's not the only reason Lillard's days in Rip City could be numbered, though.
Olshey failed Lillard years ago, the moment he let himself believe the Blazers could win a championship as anywhere near currently constructed. This latest failure may force Lillard out of Portland, hopefully onto a team that's actually committed to helping him win a ring.
Now, as the franchise's very fabric hangs in the balance, it's incumbent on the Blazers to make sure Lillard knows Olshey won't be around going forward to fail him again.