As Trail Blazers' Disappointing Season Comes to a Close, Joe Cronin is On the Clock

PORTLAND, Ore. — As is customary in the last game of the season, the Trail Blazers sent a player out to center court pregame to deliver a thank-you message to fans. This year's choice, Nassir Little, was considerably lower-profile than last year, and so was his message, thanking fans for a "great season."

A year ago, it was Damian Lillard standing in that spot reassuring fans that had sat through three months of some of the worst NBA basketball imaginable that the losing "will not continue." It did, in fact, continue. The organization has clearly learned its lesson in not making those kinds of promises, so the pregame address was a little lower-key.

One of the most disappointing seasons in franchise history, one that began with a newly healthy Lillard and big contributions from newcomer Jerami Grant and newly re-signed Anfernee Simons, came to a merciful end in a non-competitive effort against the Warriors that featured three players in uniform who were on the roster in training camp and five players signed within the last 12 days.

This wasn't the ending anyone envisioned. Since the start of training camp, general manager Joe Cronin has downplayed the organization's goals for the year and stressed that the plan was less contending for a title and more evaluating which of their players were long-term fits next to Lillard and under Chauncey Billups. But even with those managed expectations, a team with arguably the best version of Lillard we've ever seen and decent talent around him should have been in the play-in at worst.

There's no single reason they couldn't even clear that low bar. Some of it was undoubtedly injuries, but that's something every team deals with throughout any given season. Some of it, particularly the blown double-digit leads, was lack of experience, both on the court and on the bench. Lillard was the only over-30 player on the roster, and Billups will be the first to tell you he's still learning the job in his second season as a head coach. Both of them have lamented the lack of veterans on the team throughout the year. The defense, which has been their biggest weakness in recent years and which last summer's additions were supposed to address, was fourth-worst in the NBA once again.

The roster was flawed from the beginning. In another timeline, the talent level between Lillard, Simons, Grant, Jusuf Nurkic and Josh Hart could have been enough to overcome the lopsided construction. Cronin admitted back in July that they were undersized. The honesty was refreshing but doesn't change the reality that when Nurkic went down in February with a calf injury, they were doomed in most matchups with no one over 6-foot-9 in the rotation. For reasons largely out of his control, Cronin's first major free-agent signing of Gary Payton II was a misfire and he was forced to take a mea culpa and send him back to the Warriors at the deadline.

In the 17 months since he took over as GM in December of 2021, Cronin has been transparent about his goals and the obstacles in his path, and he's largely followed through on what he's said he'll do. He needed to clean up the Blazers' books after a half-decade of shortsighted trades and signings from his predecessor, and he's done that. He's professed to prioritize talent and upside in the draft, and it's hard to argue he didn't do that in taking Shaedon Sharpe seventh overall last June. He wanted to give himself flexibility for whenever the time comes to make the trade, and he's positioned himself well to do that this summer.

Cronin's next stated goal—turning what is currently a lottery team into a serious contender—is the toughest of all, and he's running out of time to do it before it's too late to give Lillard an honest chance to compete for the title he so badly wants to win in Portland.

"Timeline-wise, it's time for us to start moving quicker towards having a roster that’s ready to compete at the highest level," Cronin said on Sunday at his end-of-season press conference following the 56-point blowout loss to the Warriors.

Throughout the time he's been in the big chair, Cronin has simultaneously preached patience and given away the urgency he faces.

In that time, he's stressed that it will take multiple transaction cycles—drafts, free agency periods, trade deadlines—to build the roster he wants; at this year's deadline, Cronin characterized himself as "borderline anxious" to make the all-in move everyone knows is necessary.

"It's my job to be the voice of reason, to be very diligent, to not make a big mistake," he said in February. "To not get the wrong guy, to not overpay, to not give up on someone that could eventually become a really good player. I've got to be really smart about this, because it's trying to thread a really thin needle here. We don't have room for error. We need to get this right. We need to maximize Damian's time."

There isn't much longer he'll be able to wait. The deadline moves involving Hart and Payton, while underwhelming on the surface, were a more prudent path than unprotecting the pick they owe the Bulls to free up future firsts to trade for a lesser-impact player than could be out there to be had in June or July.

But the longer Cronin has slow-played the retool, even for understandable reasons, the tighter that needle has become for him to thread. Lillard, as great as he was this year, will be 33 when training camp opens in September. Portland tried the "two-timelines" approach this season, attempting to compete for the playoffs while developing young talent. It came at the expense of the kind of veteran depth that could have gotten them through the rough patches of health.

The leap that Sharpe took in the final month of his rookie season was at least worth some of the short-term tradeoff of losing. If the 10.5 percent chance at landing the No. 1 pick in the lottery hits next month in Chicago, Victor Wembanyama will be worth those same growing pains. But if they don't land the top pick, keeping it and taking a player won't line up with competing at the level Lillard wants to.

"I don't have much of an appetite for building with guys two and three years away from really going after it," Lillard said at his Sunday exit interview. "We get Shaedon at 19, and he's just different. His disposition and the way he listens and his mentality, that's enough 19-year-old and you won't find one that has come along the way he has. But I just ain't interested in that, and this is not a secret. I want a chance to go for it. If the route is to do that, that's not my route. I think we're all in line with knowing what we’ve got to do to put a team together to go out there and get something done."

This is the most public pressure Lillard has put on his front office in his career, even more than in the summer of 2021, when the idea of him requesting a trade was more real than ever before. It doesn't feel as much like that's imminent this time around, because there's a belief within his camp and the organization that this front office is willing to make that push when the opportunity is there.

Cronin, in answering a question about Billups' coaching job, admitted he "didn't do him any favors" with the lack of depth, which is a far cry from his predecessor insisting the 2021 first-round exit was "not a product of the roster." Cronin knows what has to happen, and knows that it will involve making some tough choices the previous front office was never willing to make.

Choices like the one between Simons and Sharpe, with the reality being that one or the other has to be moved to make a meaningful upgrade and build a team that truly fits the rest of Lillard's peak years.

Choices like potentially trading a top-five pick in a loaded draft as part of that kind of deal.

"Sometimes if you hurry or you try to speed things up, you end up trading a really good player, but that's something that we have to live with," Cronin said. "If we're committed to winning now, we have to be able to live with what the future holds for some player that we traded."

There are only two ways out of the corner the Blazers are in, and he has to pick one of them in the next three months.

The Blazers have the ammo to make a splash, if and when the right player comes available. Between Simons, Sharpe, this year's lottery pick (assuming it's not No. 1, because no GM in the league is trading Wembanyama) and future picks they can free up by working out an agreement with Chicago, they can be players for whoever the next star is that comes available. Lillard has already put his recruiter hat on, just as he did last year with Grant.

"I know there's guys that want to do it, and I'll just say that," Lillard said. "I know there's guys that move the needle. But knowing that and making something happen to make it a reality is a completely separate thing."

That's Cronin's job in the coming months.

And if he comes up completely empty attempting to do the kind of star-shopping he wants to do, it may be time to think about the other possibility. Everyone, from Cronin to Lillard to the employees charged with selling season tickets, hopes it doesn't come to that. But there's a world in which that's the path this thing takes. The only thing that's not an option is running this group back with marginal changes.

"We've done the 'tweak' thing a few times," Billups said. "I think we've got to be more aggressive than that if we want to actually do right by the best player in the history of this organization."