The offseason established a host of new story lines across the NBA that require closer inspection. Throughout August, we’re giving second thoughts to the most intriguing ones.

Portland pulled up to the 2016 offseason in a Lexus SC 430 convertible, looked at the camera, and said, “Get in loser. We’re going shopping.” With money to spend and an unwillingness to let several homegrown players leave for nothing, the front office signed Evan Turner, Allen Crabbe, Meyers Leonard, and Maurice Harkless to four-year deals worth a combined $228 million. They signed C.J. McCollum, 2015-16’s Most Improved Player, to a four-year, $107 million extension. And Festus Ezeli, the defensive center Portland needed, was brought in for a bargain: two years and $15 million, with only $8.4 million guaranteed.

What general manager Neil Olshey was looking for was security. What he got was a straitjacket. Turner, Leonard, even Harkless—20-something rotation players with upside—made it immediately clear they wouldn’t earn their keep. Ezeli missed the entire 2016-17 season because of a knee injury and was waived using the stretch provision without ever playing a minute for the Blazers. Portland, originally responsible for paying Ezeli for only one season, now has him on the books until 2019-20 along with most of that summer’s regretful deals. Crabbe, perhaps the best player of the bunch, was traded to the Nets—the very team that had extended an offer sheet to him in 2016, only for Portland to match—the following July for Andrew Nicholson, who was waived for tax relief. (The Trail Blazers will be sending Nicholson direct deposits until 2024.)

The great overspending of 2016 is now a story read to team presidents and GMs at night as a warning about what happens when you dig deep in your pockets for someone like Evan Turner. Poor decision-making wasn’t limited to Portland that summer, but no other team with that level of backcourt talent has had such restrictions in free agency since. After its third first-round playoff elimination in four years, what was an easily dismissed hot take has become a much more reasonable question: Does Portland need to trade either Damian Lillard or McCollum?

If the Blazers had lived up to expectations against the Pelicans last postseason, the rallying cry to break up their backcourt wouldn’t be so loud. Fans still remember the 2015-16 season, when Portland lost four of the team’s five starters over the offseason yet still managed to finish in fifth place in the West and lose valiantly to the Warriors in the second round. The hope was that if the team could just upgrade around their star guards, either via free agency or through its surplus of young talent, it could take the next step. Locally, a rabid fan base protected the trio of Lillard, McCollum, and coach Terry Stotts even as the team continually hit its head against its ceiling.

But the world—in the form of Anthony Davis and Jrue Holiday—came crashing down on them this April. Portland, the West’s 3-seed, was swept in humiliating fashion after one of the most inspiring second halves of the season. The Blazers went 27-12 to close out last season as Lillard progressed from man to rocket, from rocket to MVP candidate, and from MVP candidate to first-team All-NBA member.

Yet New Orleans eliminated Portland with one of the most basic defensive concepts: ruthlessly doubling their most important player. Swarmed, Lillard couldn’t penetrate, find a decent shot, or keep the ball safe. (He averaged four turnovers per game during the series, the worst of his career in either the regular season or the playoffs.) The offense went limp without him at full strength. McCollum is at his best when kept off the ball, but he couldn’t provide playmaking relief. Help also didn’t come from Jusuf Nurkic, whose confinement to the post was exposed by Anthony Davis and Nikola Mirotic. Lillard and McCollum’s defensive deficiencies were exacerbated. It was carnage.

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The gaping holes in the frontcourt and on the wing are Olshey’s scarlet letter to wear, but the shortcomings in Stotts’s game plan were unignorable. Portland was successful in the second half of the season because it ramped up 3-point attempts and concentrated on creating more space for Lillard. The surrounding cast snapped into consistency as a result: Al-Farouq Aminu, Harkless, and Turner all saw an uptick in deep shooting during that stretch. But the illusion of a modern offense was wiped away in the playoffs. The wizard behind the curtain was exposed; surprise, it’s iso ball.

During the regular season, Portland finished last in assists, and behind only OKC and Houston in passes per game. In some ways, the Blazers methodology aligns with that of the Rockets. There is little ball sharing in Stott’s offense (to be fair, there are few players worth sharing the ball with). It’s operated by two isolation-happy guards. Lillard and McCollum account for more than 55 percent of the team’s shots off drives, an almost identical percentage to James Harden and Chris Paul’s in Houston. But, if need be, they can also rely on Eric Gordon’s bag of tricks to supplement, whereas the Blazers’ only other adequate playmaker is Turner, who’s too limited to be dependable. Stotts doesn’t have the spacing threats, the self-shot creators, or the paint options to thrive without sharing the ball. The problem is—yes, we’re not to the root of the problem yet—he doesn’t have passers, either.

That’s the case for why Olshey would trade McCollum or Lillard. Maybe it’s the case for Olshey losing his job, too. Liquidate what they have for assets. Blow it up. Start over. Try trading for another star. They’ll never beat the Warriors as is. It’s something Olshey seems to know, yet is not fazed by. Before the playoffs began, he told SB Nation’s Paul Flannery as much:

“This narrative that if you don’t win a championship then it’s not worth competing, that’s a false premise,” Olshey said. “There’s got to be an intrinsic joy of watching your team play well and compete. If it’s just about the end result and not about the journey, then what’s the point?”

The Blazers are now headliners on the “good regular season, bad postseason” tour. They’re officially the team that hangs on for another year, replacing the 2017-18 Raptors, and the 2016-17 Clippers before them. Olshey’s inaction gives the impression that he’s waiting out Golden State’s reign. And because of his own decisions, Portland kind of has to. The Blazers aren’t rebuilding, and they aren’t changing their strategy—Nurkic was re-signed to a team-friendly, four-year, $48 million deal in July—yet they don’t have enough to be “win-now.” Lillard has resented the notion that Portland is “waiting” until the Warriors dynasty is over, and is showing signs of impatience. But it might not be the worst time to be stuck in between. Next summer, Klay Thompson will be an unrestricted free agent, and Draymond Green hits the market the summer after that. It’s within reason that the paydays Thompson and Green feel they are due won’t be reasonable to Warriors president Bob Myers, given the team is already flirting with the repeater tax. The 2019-20 season is Portland’s last one with Turner, Leonard, and Harkless on the books. Lillard, then 29, will have one year left on his contract.

For as quiet as the Blazers offseason seemed, the franchise does have room to tweak its identity. With Ed Davis gone, Zach Collins is primed for a breakout season. Portland brought on Seth Curry to a one-year, $2.8 million deal to replace Shabazz Napier. Curry was out with a fractured left tibia all last season, but played the best basketball of his career the season prior with Dallas. If he returns to form, the younger Curry could fill multiple gaps for the bench: playmaking relief, dynamic passing, and runs-in-the-family 3-point shooting. And after a season of regression, there’s the expectation that McCollum bounces back.

None of these minor alterations are sure things. We’re talking about Wade Baldwin stepping up, and Caleb Swanigan possibly earning a spot in the rotation. Like they did in the summer of 2016, the Blazers are betting on youngish players blossoming—though it’s a low-reward gamble for a franchise that’s paying the luxury tax. Does earning north of 50 wins and advancing to the second round of the playoffs again make Olshey’s refusal to budge on Lillard or McCollum worth it? In an era when stagnant teams are encouraged to start over, Portland is choosing to risk being bad in the playoffs over just being bad altogether. There’s a chance that the Blazers’ approach of maximizing the potential of their current core intersects with another team getting hit hard with health issues, or making a trade that backfires. Right now, they’re the fallback boyfriend, waiting around just in case the current one doesn’t work out (or gets drastically injured.) That possibility is likely why Olshey will see it through: Why throw away something that isn’t necessary broken? Either way, the Blazers are headed for an inevitable reboot. When Lillard and McCollum’s contracts are up in 2021, Portland’s window is, too—but so are all the commitments currently tying it down. That’s the benefit of signing a cluster of contracts all at once—it’s a chance to start over, no matter what happens.