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In the seven seasons since LaMarcus Aldridge’s departure for South Texas, the Trail Blazers have been trapped in a dead sprint atop the league’s notorious treadmill of mediocrity. The architect of the teams of the past decade, Neil Olshey, seemed perfectly content with fielding good but not great teams who sold tickets but didn’t actually contend. Which is stupid!

When you have one of the greatest point guards of all time under contract during his prime, you should, you know, be actively trying to win championships. You should construct a roster around him that makes sense in the context of the modern NBA. You should do lots of things that Olshey adamantly refused to do while he was promoting the teams he’d built around Lillard as true contenders, a reality which, towards the end, became painfully obvious as only existing in his own imagination.

Olshey was an objectively interesting character in the annals of Blazers history — a guy who went from a struggling commercial actor in Los Angeles to GM of the Clippers in a remarkably short span before taking over the Blazers’ front office and drafting an obscure mid-major point guard with the sixth overall pick in the draft. He built some very good basketball teams. He was a canny accumulator of power and, like all those who remain in power for long periods of time, he understood how to cultivate members of the press in order to hold onto it. But somewhere between establishing an abysmal front office culture and chewing out Dan Dickau for not CCing him on an email he completely lost track of what championship-level NBA teams looked like. The league changed around him, and he either didn’t notice or didn’t care.

One of the main problems with Olshey was that he had a very fucking powerful imagination. You could tell that he believed what he was saying. His petulant assertions at the outset of last season that a third 6’3 guard playing small forward, the additions of a few washouts, and a rookie head coach would be what would finally push his teams toward the promised land were openly mocked. By the end he was a joke, and it was indeed very funny when he was finally given the boot out the door.

The remaining question is whether or not the Atlas years of Lillard’s career that were wasted after it became obvious that Olshey needed to go are going to represent an ignoble and ultimately tragic final lines of the Damian Lillard chapter of Blazers history.

The hope is that maybe, if a few things go the right way, they’ll end up as merely a prelude to a golden age of actual championship-level basketball, and ultimately to the crowning achievement of Lillard’s career: bringing a championship to Portland for the first time since 1977, after decades of the basketball gods punishing the team’s diehard fanbase with wildly gratuitous levels of heartbreak.

The story of Damian Lillard and Portland deserves to read like great literature. Not a cautionary tale, not a tragedy — a triumph of the highest order. At the very least, he deserves the opportunity to write his own ending without having one hand tied behind his back.

Under new management

Joe Cronin is a nice guy. When he talks to the media, he’s personable, thoughtful, and seems generally honest — a stark contrast from his predecessor Olshey, who towards the end could best be described as things like “full of shit” and “patronizing” and “delusional.”

Cronin has been in the organization since being hired as an intern during Brandon Roy’s rookie year in 2006, and in addition to being the polar opposite of Olshey in every imaginable way personality-wise, he actually understands the CBA and what a modern NBA team, especially one built around Damian Lillard, should look like.

When Olshey would talk about free agents, trades, the cap, etc. he always kind of reminded me of a senator who flunked econ in college but became really good at pretending to understand the economy when it came time to talk to the media. He was a good talker. Cronin is more like an economics professor turned senator who’s trying to figure out how to be a politician on the fly. The good news is that he appears to have the chops for it, having quickly earned the confidence of the organization’s key power brokers: Lillard, Jody Allen, Chauncey Billups, and Dewayne Hankins (President of Business Ops). Also key to his interim tag being removed was the simple fact that he’s the most knowledgable person in the world when it comes to the Blazers. Having worked within the organization for 16 years (and having watched Olshey intermittently light things on fire for seven of them), he knows better than anyone else the intracacies of the roster and its payroll, how to operate in the Portland market, and how the Blazers can navigate the narrow straits that will push them from where they are now to where they need to go.

In the past 11 months, Cronin has shown himself to be a canny operator on the level of Olshey, but in his own way, in which he doesn’t needlessly antagonize people. All things considered, he very deftly seized his opportunity to fill the vaccuum created by the ouster of Olshey and now finds himself, after 16 years, with the lion’s share of power within the franchise. Now, entering Damian Lillard’s age-32 season, we’ll see what he can do with it.

The opening night roster: weird on purpose

By Cronin’s own admission, the roster as currently constructed doesn’t make a ton of sense. There’s a practically even split of established veterans and unseasoned young players that you practically never see. In the modern NBA, teams are either all in on chasing a championship, which means having mostly veteran players who fit neatly into their roles, or they’re chasing a lottery ticket and actively trying to lose as many games as possible while playing almost exclusively young players. The Blazers’ current roster, by contrast, is like a bunch of puzzle pieces that don’t quite fit together — but this is by design.

Cronin’s knows that the team likely isn’t a contender this season, at least in its current form. And that was unlikely to be the case in the first year of the post-Olshey shake-up. The back end of last season, this offseason, and the coming season have been about raising the overall talent level of the team. Trading away McCollum, Covington, Powell, etc. and furiously tanking into the top ten of the draft netted Josh Hart, Keon Johnson, Justise Winslow, Shaedon Sharpe, and the pick that was subsequently flipped for Jerami Grant — players who actually make sense around Lillard: athletic, tough, two-way guys who can shoot. It also opened up the cap space to sign Gary Payton II (last seen playing high-level basketball in the Finals despite coming back from a broken elbow). Tanking the end of last season also opened up valuable developmental minutes for Ant Simons, Johnson, Trendon Watford, and Nassir Little (who Cronin somehow signed to what feels like a preposterously low extension on the day of the deadline).

The decision to trade away McCollum was no longer hard to stomach after so many insipid years spent watching the roster bonk its head on its ceiling in the playoffs. Enough has been said about the Lillard-McCollum fit elsewhere, everywhere all the time for many years that we don’t need to get into it here. But it was past time for a change and the trade and its subsequent consequences roster/development-wise have all worked out about as well as could have been hoped, despite the gut punch that came with the loss of the Pelicans’ lottery pick when they snuck into the playoffs (which, for the record, was some bullshit).

Cronin further showed that he knows what he’s doing when he hired ESPN’s Mike Schmitz, one of the best talent evaluators in the world, who will be a GM himself probably sooner than later. I’m admittedly biased because I’ve been following Schmitz’s work since his first days at DraftExpress, but bringing him on board was a coup. His work behind the scenes, along with the rest of the team’s new brain trust, will be critical in shaping the future of the roster.

The veterans on the opening night roster are very good players: Damian Lillard (who at least according to the preseason eye test appears to be back to his old ways), Jerami Grant (The Forward That Was Promised), Jusuf Nurkic (still 15% worse than it seems like he has the capacity to be), Josh Hart (fucking awesome), Gary Payton II (arguably the best perimeter defender in the world), and Justise Winslow (can’t shoot but does everything else well). And again, they all fit stylistically into a modern, switchable defensive scheme around Lillard — who’s been a subpar defender but isn’t nearly as bad as he’s looked for the past seven seasons sharing a backcourt with a much worse defender while carrying nearly the entire offensive burden — and most of them are at least passable floor spacers. Which is to say that they all fit into a coherent, modern team-building philosophy. The rosters of the Olshey Era, to put it mildly, left a bit to be desired in this department.

The players who represent the Blazers’ young core fit the same mold. Cronin, Schmitz and co. have shown that they value long, athletic competitors who will complement Lillard if properly developed. The young core consists of Anfernee Simons, Nassir Little, Shaedon Sharpe (who will shortly have his own feature written on him here at Blazesketball dot com because he is the fucking truth and the future of the franchise), Keon Johnson, Trendon Watford, Jabari Walker, Troutdale’s own Drew Eubanks, and Greg Brown III. These guys represent the most underrated collection of young players in the league; the first six names listed (I’m counting Jabari despite him never having played a minute of regular season basketball, fuck the haters) all project as starters and plus rotation players.  

The issue is how to walk the line of developing enough of the young players so that they can immediately help the team (and also play enough minutes to showcase their value to other teams in the event that they’re traded for a bigger fish) without sacrificing too many wins in the short term.

Defining success  

The general theory of what Cronin is trying to do implies that by next year, only the strongest players from each faction will be left, and they’ll meet somewhere in the middle. If a star player on another team becomes available, some of the young players will be packaged with future picks and Cronin will push all his chips into the center of table and go all in.

But again, the organization isn’t, at least at the outset, all in on trying to win a championship this year. Of course, if things go unbelievably well and they think they have a shot, that all-in move could be made, but that seems pretty unlikely at this point. What fans should be hoping for is a passable record, somewhere around .500 by the time the team gets through its hell-on-earth section of the schedule that begins the season. If they’re way below water on December 15, the day players signed in the offseason are eligible to be traded, expect Nurkic and Hart and maybe some of the young players to be shipped out of town. If they’re, say, five games above .500, maybe they’ll get frisky and try to go for it. But the most likely outcome is that they hang somewhere around .500 and stand relatively pat, try to make a little postseason run, and play for the offseason — where they can make the moves necessary to come into the 2023/2024 season as true contenders.

A successful 2022/2023 season would look something like this: finish in the top eight in the West; develop the young players, particularly Sharpe as much as physically possible; avoid serious injuries to any of the starters; win consistently enough and provide a big enough of a role on offense to convince Grant to re-sign; win a playoff series or two. If the Blazers are able to win some playoff games and head into next season with momentum, they’ll have a chance to emerge as true, top-shelf contenders for the first time in Lillard’s career. It would be great if they could sweep away years of team-building malpractice with one season of tanking and one offseason of sweeping roster changes and all of a sudden be a threat to win the title. But, unfortunately, believing in that would require seeing things through rose-colored glasses — and if you’re a Trail Blazer fan, you tossed yours in the trash a long time ago.