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Trail Blazers v. Damian Lillard: The Argument for Joe Cronin

What happens when you fight and pretty much everyone is right?

Utah Jazz v Portland Trail Blazers Photo by Abbie Parr/Getty Images

The Portland Trail Blazers have been caught in a whirlwind of speculation, anticipation, and condemnation since star point guard Damian Lillard requested a trade on July 2nd, 2023. No event has caused this much stress, nor put Portland so squarely into the NBA limelight, since they had to choose between Kevin Durant and Greg Oden in the 2007 NBA Draft.

In the midst of turmoil, plenty of people have offered opinions on the principals involved. Yesterday we addressed some of the criticisms leveled at Lillard, trying to look at the situation through the eyes of an aging superstar caught in forces beyond his control. The same may be said of Blazers General Manager Joe Cronin, ostensibly at the helm of the ship, but constantly battling storms in the 18 months since he took over.

How much responsibility does Cronin bear for Portland’s current condition, and how much power did he have to change it? If Lillard’s hands are relatively clean, are Cronin’s stained?

Opinions on the matter seem to be divided, as indicated by these submissions to the Blazer’s Edge Mailbag:


Joe Cronin is a fraud! I can’t believe you aren’t writing about this every day. He’s blown apart this team right under Lillard and driven him off. How incompetent would you rank him? I know you didn’t like the last GM. Why not go after Joe?



The antipathy toward Joe Cronin right now is profound. Most of it seems derived from the idea of trading Dame, not necessarily the entirety of his still very brief track record. Some folk even refuse to give Cronin credit for drafting Scoot and Shaedon, preferring to applaud the work of the scouting department instead, which somehow bypasses the point that the department works for the GM and not the other way around.

Have you ever seen such a reaction to a new Blazers GM?

It seems so very America in 2023: If something doesn’t go the way you like then burn it down!

I honestly don’t get it.

David N.

As with our last post, we need to take a deep breath here and consider the larger context before getting worked up about who’s at fault for what.

Nobody wants to hear it, but the short answer to this question is that you can only choose from the options available. You can order fliet mignon at McDonald’s all day long. You’re not going to get it. No matter how many times you give them five bucks, they’re going to return different versions of a Big Mac.

If you want to understand the Blazers’ predicament right now, think of Joe Cronin as the dad taking a van full of kids on vacation, looking for something decent to feed them. He already stopped by Mickey D’s and saw the menu. He had the option to fork over five dollars twenty times, stuffing them with fast food burgers. He opted not to, sticking his hundred back in his pocket and leading them back outside. Now he’s walking down the street, trailed by a grumpy, hungry family, muttering to himself, “There’s GOT to be a restaurant here somewhere...”

So far, no luck. And boy, are those kids getting loud!

Before we get too far into that, let’s take a look at how we got here.

Cronin’s History

It seems like an eternity ago now, but Joe Cronin only took over the General Manager’s seat in December of 2021, 18 months ago. He was designated an interim until May, 2022, when he was named to the post officially.

From the start, Cronin was no stranger to the organization. He had served as a scout and cap expert under multiple GM’s—Steve Patterson, Kevin Pritchard, Rich Cho, Chad Buchanan, and Neil Olshey—dating back to 2006. He was promoted to Director of Player Personnel in 2014, then named Olshey’s Assistant GM in 2021.

Deep verticality through the infrastructure likely recommended Cronin as a strong candidate for Portland’s opening when Olshey was dismissed in 2021. Cronin was familiar with the franchise’s culture, history, and power players. Few candidates would have been more “Portland” than he.

Cronin’s moves and statements since taking over the lead executive role have shown a willingness to change the culture, and indeed the roster. But given the circumstances, any such transition would involve latency. Cronin would inherit franchise inertia full force, far more than an “outside” executive would have. The voices of the enfranchised within the organization—owners, star players, other points of power—would be both familiar and amplified. Eighteen months isn’t long to affect drastic change, let alone in the family you grew up in.

Inheriting a Fix-Me-Upper

Though Neil Olshey, Cronin’s predecessor, was terminated for violating organizational policy and not incompetence, the condition of the franchise he left behind was hardly perfect.

The Blazers reached the Western Conference Finals in 2019, high on their prospects for the future as Lillard and CJ McCollum came into the richest part of their prime years.

The 2020 season brought a losing record followed by a first-round playoff exit at the hands of the Los Angeles Lakers. The regular season looked better in 2021, but Portland once again fell in the postseason, this time to the Denver Nuggets, whom they had conquered on their way to glory two years prior.

Following that loss, Olshey fired long-time head coach Terry Stotts, replacing him with first-timer Chauncey Billups, a former associate.

The team got off to a mediocre 10-10 start in the 2021-22 season. The record headed south about the same time Olshey was suspended. Nine games after, Lillard would shut down for the year, opting for surgery to correct a chronic abdominal issue.

A snapshot of the franchise as Cronin took over would have showed instability at every level.: new coach, injured superstar, muddled supporting cast. Cronin himself was new to this level of management and ownership—outside of the intermediary Vulcan, Inc. layer—was no more than three years old.

In that kind of environment, change isn’t just a matter of deciding what to do. Leaders have to answer questions like, “Why?” and “For whom?’ and, most critically, “Who do I have to convince to get this done?”

Priorities and Aims

Ultimately, an executive is responsible to his or her own vision. One of the basic rules of high-level leadership is to stand or fall as yourself. As soon as you sacrifice your internal vision—that gut instinct about what’s right and wrong—you’re going to get blown about by the forces surrounding you until you’re fired anyway. Might as well be yourself and take the chance of succeeding.

Organizational polity sometimes puts boundaries on that vision. Portland’s chain of command is more obscure than most, but it’s a good bet that fiscal sanity has been among the highest priorities of owner Jody Allen and Vulcan, Inc. during Cronin’s tenure. If true, his vision would need to shape itself to those realities.

The Blazers did not exceed the luxury tax threshold last year nor do they give any indication of doing so this year. They’ve given up veteran talent and avoided committing to expensive, longer-term contracts. With a few exceptions, signings and acquisitions have trended towards minimum or rookie scale.

The Blazers have dedicated dollars to their incumbent players: a long-term extension for Lillard, re-signing Jerami Grant, Anfernee Simons, and Jusuf Nurkic. Though they no doubt value each player, the latter three moves could be seen as defensive, not losing trade assets by letting those players walk without compensation.

A look at the major players the Blazers have lost and acquired during Cronin’s tenure will tell the story of the last year and a half:

Outgoing: Robert Covington, Norman Powell, CJ McCollum, Larry Nance, Jr.

Acquired, then Moved: Josh Hart, Drew Eubanks, Gary Payton II, Cam Reddish

Acquired and Still Present: Jerami Grant, Matisse Thybulle, Keon Johnson

The Blazers are still spending money. Grant, Thybulle, and Johnson account for $41 million in salary this year. The departed players outweigh them, making $102 million in aggregate next season, far more when the contracts of McCollum and Hart mature. Were winning the only priority, the Blazers could still use Hart. Truth be told, they could probably use Nance, Jr., Covington, and Powell as well. Keeping them at a steeper price tag wasn’t in the cards.

Besides restraining expenses, Cronin had a parallel expectation to massage: the expectation to win and mature, expressed by franchise cornerstone Damian Lillard.

As we detailed yesterday, Lillard’s definitions of success and Portland’s had been diverging by degrees since their relationship came to full flower in 2015. By the time Cronin took the reins, Lillard had been through four sets of starting forwards, two and a half centers, one pandemic, and a roller coaster of national attention coupled with local futility. Portland’s playoffs loss to the Nuggets in 2021 had been a watershed moment, confirming that the current course would not lead to success. Lillard wanted change for the better, and he wanted it soon.

Cronin stepped into the gap between these parties, tasked with turning around a slow slide to please his star, keeping expenses down to retain the trust of ownership, and living out his own vision for the future of the franchise.

Conflicting Messages

Out of this tug-’o-war came a series of conflicting messages.

Cronin’s public refrain, oft-stated and consistent to this day, is that the aim of the Trail Blazers is to build a contender around Damian Lillard.

Looking at Portland’s actual moves, it’s hard to credit that desire as their primary motivation. They moved McCollum, the second best player on the team, for Hart and a draft pick. They’d later trade Hart for rookie-scale hopefuls Thybulle and Reddish, but retain only one. Trading Covington and Powell to the Clippers became a de facto salary dump. Talent sent out exceeded talent taken in, at least at the veteran level.

Theoretically aspiring to win, the Blazers tanked in the latter stages of the 2021-22 season, earning their way into the 2022 NBA Draft lottery with 27 victories in 82 games. Lillard was their representative on the dais for the drawing. He looked visibly disappointed when they did not advance to a top-four position.

Selecting Shaedon Sharpe—an ultra-athletic, but speculative guard who had played zero minutes of high-level competitive ball before being drafted—did not improve Portland’s immediate outlook.

Lillard came back for the 2022-23 season stronger than ever. His team did not. They got off to a mediocre 11-9 start. By mid-season, it was clear they would battle for a lower playoffs seed, at best. Not long after the All-Star break, Lillard shut it down again and, like a frustrated Nemo, the Blazers returned to the tank...a strategy that Lillard vowed his team wouldn’t have to repeat.

At that point, the cracks in the foundation were evident. Cronin spoke of contending, but the Blazers were tanking. Cronin spoke of building around Lillard, but every move Portland made resulted in the roster getting younger, to the point that Lillard, Grant, and Nurkic stood on an island as the only players above 28 years of age. What the Blazers said and what they did were two different things.

We do not know for sure, but we can guess that this added hot sauce to Lillard’s abrasions. Falling short again would bring the half-dozenth course change in the past eight years. At some point, explanations don’t matter. If you have to explain why we need to turn around for the sixth time on the same trip, I’m going to assume that you’re lost.

When tanking paid off and the Blazers fell into the third-overall spot in the 2023 NBA Draft, Brandon Roy—Lillard’s predecessor as face of the franchise—sat on the dais beneath Portland’s logo. When the Blazers drafted Scoot Henderson, the hottest young point guard to come down the pike for some time, more than one person guessed we were looking at Lillard’s successor as well.

As it turned out, Lillard himself was among them.

Judging Cronin

To this point, the factual evidence against Cronin, at least in relationship to Lillard, appears to be damning. He said he’d build up. The team slid down. But that’s just the surface layer of the story.

Before we judge Cronin guilty (or duplicitous or incompetent), we need to probe deeper into subtext and context.

Are Damian Lillard and the Trail Blazers inseparable?

That Cronin has failed to fulfill his stated goal is inarguable. He has admitted such.

To whom is that a failure, though? The obvious answer is to Lillard himself. Does that automatically make it a failure for the franchise and its fanbase?

Damian Lillard is the most charismatic and well-known player in Trail Blazers history. Because of his talent, magnetism, and the muted track record of his teams, his shining star has become synonymous with the franchise itself. You cannot speak of the Trail Blazers between 2012-2023 without naming Lillard first, last, and always.

That identity enmeshment was encouraged by the franchise itself. Their one-man highlight reel was also the ultimate distraction. Any time the record dipped, after every playoffs loss, in the midst of every struggle and woe, the Blazers could point to Lillard and say, “This is us!” It helped Dame. It helped the fans. It cemented Portland’s popularity and reputation. Everybody won.

That this kind of relationship might be unhealthy, disguising issues rather than solving them, was a taboo topic. Ruffling feathers of Golden Geese is discouraged.

Up until July 2nd, any suggestions that the relationship between Lillard and the team might be fracturing, or that Lillard alone wasn’t enough to carry a team, or that the Blazers might want to look at trading their star before he aged out, were hailed as personal, near-blasphemous insults by organization, teammates, and fans. Analysis, and sometimes common sense, went out the window. “Loyalty” became the currency of the realm.

When Lillard was in his prime, playing for a team still capable of ascending, the distinction was academic. Who cared? They were going onward with Dame no matter what and they did pretty good.

Today Lillard is 33, the Blazers are stalled, and he’s requested a trade. Having lived a decade in “Dame = Blazers” mode, we fumble for the language to describe this new reality. The heart of the franchise is asking to depart. It feels surreal, impossible, like dividing by 0. Check your work. Something must be wrong.

No moment of the summer was as vibrant as Scoot Henderson taking the floor for Portland’s first Summer League game and scoring 13 in the first period. The event itself wasn’t that significant. Summer League doesn’t matter much. Henderson would go down with a shoulder injury during that same outing. But Blazers fans greeted the performance the way parched explorers greet water in the desert.

The breath of fresh air washing across Blazers nation at that moment was simple. Oh wow! We have alternatives.

With so little evidence behind it, the sentiment is vastly overstated. It bloomed in the void left by the Lillard Era, where no alternative was needed, and no such possibility existed.

The first question to be answered in the “Did the Blazers fail Dame?” debate is whether failing or pleasing Damian Lillard should have been the primary concern of the franchise. It mattered, surely. But does disappointing Dame automatically betray Portland’s mission statement and purpose?

The Blazers and their superstar are still struggling with that question as they seek an acceptable trade to take him out of town.

As long as Dame was the center of Portland’s universe, their goal was to please and foster him. Everyone was happy with that; the point didn’t have to be debated.

Now, for perfectly justified reasons, Lillard has asked for a change. Doing so, he answered the question for us. The star himself is not only claiming, but insisting, that he and the organization are not inseparable. The franchise can no longer act as if they are.

That is at least half of the meaning behind Cronin’s current declaration that, while the Blazers remain committed to helping Lillard forward, they have to do what is best for their franchise.

That distinction is a shock for all those who experienced an era where “best for the Blazers” and “best for Dame” were synonymous. That doesn’t mean the new impulse is wrong, given the changing situation.

In terms of the past decade, the current course is certainly a failure. In the life of the franchise as a whole, it could also be defined as an opportunity for restoration, depending on how it’s handled.

Was it possible to build around Dame?

The second prominent question that rears its head in these discussions is whether the team and Lillard had to get to this point in the first place.

In order to condemn Cronin for taking a wrong turn, we need to show there was a right one. Could Joe have ordered a filet off of the McDonald’s secret menu?

Nobody can answer this with certainty. Here are the things we’re fairly sure of:

  • The Lillard-McCollum pairing was not working well enough to carry it through to the end of Lillard’s career. They were good, but they had the misfortune of skill duplication, defensive weaknesses, ultra-expensive contracts, and always being second to a superior guard pairing in their own conference. The Blazers could have remained good behind CJ and Dame, but would not have become championship contenders.
  • Each year, the Lillard-McCollum tandem became more expensive contractually. Each year, the Blazers got a thinner return on talent and sacrificed more cap flexibility trying to find the right combination of players to put around them.
  • By the time the Blazers traded McCollum, his strengths and weaknesses were well-known. They were not going to get a huge star for him.
  • Beyond that, the Blazers had no more than the mid-level exception with which to lure free agents.
  • The easiest, cheapest way to improve a roster is through the draft. The Blazers still had that avenue open, but were beginning to trade future picks for present assets that didn’t move the needle. If McCollum and Lillard stayed together, future draft prospects were muted.
  • Via Shaedon Sharpe and Scoot Henderson, the Blazers have expended draft picks to improve as much as they could. Given the age of the players, is it not reasonable to assume those moves would pay off during Lillard’s remaining prime.

Given these factors, building around Lillard was a long-shot proposition to begin with. Portland needed some kind of miracle to make it work. That was not forthcoming.

If the failures of a team can be traced to a GM’s strategy, criticism is more than warranted. If no meaningful progress down a path is viable and no miraculous rescue is on the way, a General Manager cannot be faulted for those lacks. It’s ok for your friend to buy a Powerball ticket, hoping. It’s unreasonable to lecture them for incompetence when it doesn’t win.

What about the communication gap?

All of that said, what Cronin claimed the Blazers would do and what they actually did are two different things. Some accountability is merited on that account.

Did the team fail in their goals or was Cronin dissembling? Best guess: it was a little of both.

I do not know Joe Cronin and I have not spoken to him on this, or any other, matter. But everything I’ve picked up on him from reports, press conferences, and people who do know him points to genuineness. I, personally, believe that Cronin did want to build a contender around Damian Lillard and believed the possibility was real. I do not believe he was lying.

Even so, Cronin must have realized the difficulty inherent in the attempt. The possibility of falling short likely crossed his mind. To whom was he to communicate that, though? And how? Even if he knew the odds were long, could he have said anything other than he did?

What would have happened if, 18 months ago, Joe Cronin had stepped to a microphone and said, “We really want to build forward, but it’s going to be hard. There’s a good possibility that we’re going to have to rebuild. That would mean trading Damian Lillard and probably angling for draft picks. But hey, we’ll try. Any questions?”

Um...yes. All of them. And Mr. Lillard would like to speak to you, right now.

Every time Cronin spoke, he addressed those same divergent audiences we mentioned earlier: ownership demanding an affordable and viable team, a superstar demanding new progress, a fan base begging for good news, plus competing teams wondering if they could fleece the Blazers and their new GM.

Cronin had no way of predicting how his efforts would turn out. The only way to reach a desirable end is to define the desire, then aim towards it, committing passion and resources to the mission. That’s exactly what Cronin did.

Desirable and the possible turned out to be two different things for the Blazers. While Cronin addressed that tension in practical terms every time it arose, overall he kept the course charted to where he hoped to go. The only alternative was to acknowledge the plan failing, which inevitably would have caused that failure prematurely.

If Cronin can be faulted in any part of his communication, it’s in a bit of naivete, perhaps occasioned by inexperience.

The only truly head-scratching moments in the process came two months prior to the end of the season, when all the buzz coming out of Blazers HQ was about the “big trade” upcoming. I think the front office believed that they could swing a major deal this summer. Letting that out into the ether before it happened made the fall worse.

It also became the last instance of serving up a proposed plan to Lillard that didn’t work out. You could practically feel the “thud” when Cronin announced, post-draft, that the Blazers intended to keep both Lillard and Henderson. That seemed nearly as far-fetched as earlier whispers of pulling off a trade for the reigning league MVP.

Where have the Blazers ended up?

For all the crossed communication and realigned expectations, the Blazers are in a decent position going forward. Joe Cronin’s left hand may have pointed to the horizon of Keep Dame Island, but his right hand seems to have tilted the wheel subtly toward Sail Onward Seas.

Portland has Henderson and Sharpe in tow, plus Anfernee Simons if they care to retain them. That’s as good of a young guard corps as anyone has in the league. Their frontcourt still needs help, but with the timeline for improvement lengthened, further drafts and trades have a better chance of succeeding. The Blazers remain under the luxury tax threshold. They can also expect some return for trading Lillard and possibly other veterans.

Ascent to elite status would have been preferable, but if the Blazers had to end up here, they haven’t done a bad job of it. The cupboard isn’t bare. The rebuild is, at minimum, one year underway, with the promise of Henderson accelerating it beyond its time.

Once the Blazers get past this transition period, they have a chance of coming out of this smelling like a rose. Putting his team in that kind of position despite the turmoil may end up to Cronin’s credit.

The Verdict

If there was a real path forward for the Blazers, keeping Damian Lillard and vaulting into contention, then Joe Cronin missed the boat and should be criticized.

If that goal was not attainable over the last 18 months, it’s hard to see where Cronin went wrong...or that he could have done much better.

A brand new GM kept his star in the fold despite multiple reasons for him to leave, drafted new and acclaimed talent, kept fiscal sanity for the owners, refused to take on bad deals, navigated past the natural tendency towards inertia, and communicated skillfully, if not exactly completely, while doing so.

The amount of juggling necessary for Cronin to get to this point is incredible. Doubly so when you consider the chaos and drama surrounding the franchise when he inherited the position.

Yesterday, we claimed that Damian Lillard was perfectly justified, or nearly so, in asking for a trade. He was probably overdue and should be credited for hanging on so long.

Examining the foregoing, we can also say that Joe Cronin has done a pretty good job walking through the past season and a half, even if circumstances and outcome have been less than ideal. In fact, for a first-time general manager, getting this far in this shape has been phenomenal. He could have done much worse.

Were this a trial of Lillard v. Cronin, we’d have to find that neither one of them has done anything inherently wrong. Sometimes, when the interests of two parties don’t coincide, they have to figure out how to separate and go forward with as little pain as possible. It’s going to cost both of them something, but hopefully it doesn’t cost either of them everything.

The Next Test

It’s a truism that divorces remain amicable until it’s time to divide up the bank account and custody of the kids. Executing an agreement in reality is much more difficult than it looks theoretically, even when the sides are friendly.

The next huge test for Joe Cronin will be consummating a deal for Damian Lillard. That’s the “bank account and kids” of this whole process.

The situation is complicated greatly by Lillard’s apparent insistence on the Miami Heat as his preferred (read: only) destination. This has the dual effect of driving his trade value down and putting Cronin face to face with Pat Riley and company, the Marlon Brando-esque Godfathers of the NBA. The Heat won’t be leaving horse heads in Cronin’s sheets, nor making offers Portland can’t refuse, but the staring contest across that table may be long.

The only chip Cronin holds is Lillard’s multi-year deal and his willingness to sit on it. Given Lillard’s reputation and profile, holding him captive is not a palatable option. As soon as the Heat become certain of that, however, Cronin’s last pretense of strength evaporates.

By every other conceivable measure, the power balance tilts toward Miami in this exchange. Were this the Copacabana, Riley would be Rico and Cronin, poor Tony. Now all Joe has to do is rewrite the more thing to salvage out of this mess.

Before we render final judgment on Cronin’s performance during the waning Lillard Era, waiting to see what he pulls out of the final trade might be prudent. Though he’s not been able to bail Portland out of their troubles, he has snagged assets and put his team in decent position despite the difficulties. Dealing with Miami may be his greatest test in that vein.

If Cronin can pull something significant out of the exchange, he should be celebrated. At that point the path forward will be clear for him to rebuild without so many competing influences.

There’s also a chance that Cronin becomes known as the GM who traded Dame for nothing. At that point, he’s going to be buried in scorn no matter what else happens.

Either way, Portland’s GM won’t get rest, or a final evaluation, until that deal is settled. It’s the final exam in a crash course called Managing a Franchise Through Trying Times. If he blows it, he’ll probably have to repeat the class, just with a different cast. If he passes, you might as well make him the professor.