Damian Lillard and Adrian Wojnarowski.

In the past 15 years, there have been two inflection points in how the biggest stories in the NBA are covered: LeBron James going to Miami in 2010 and ESPN signing Adrian Wojnarowski in 2017. But we may look back at this summer’s Damian Lillard saga as a third, considering just how inextricable the media was from the flow of negotiations all offseason.

Lillard announced his intentions in two separate interviews early in the offseason. One was during ESPN’s NBA alternate broadcast Stephen A.’s World with Stephen A. Smith, while the other came with Brian Custer on Showtime’s The Last Stand. In each interview, Lillard made it clear he would consider asking for a trade if Portland did not improve its roster. And with Custer, in an interview that aired after the Trail Blazers won the No. 3 overall pick in the draft lottery, he went so far as to give a list: Miami and Brooklyn.

Portland chose not to trade its draft pick in late June. That’s about when Lillard’s agent, Aaron Goodwin, started popping up with quotes all over basketball media. And it was an open joke across the NBA content universe that inevitably, Turner Sports’ Chris Haynes would break the news if and when Lillard ever asked out. The two are known friends.

On July 1, Lillard indeed did request a trade. And Haynes did indeed break the news — with a graphic prepared and everything. 

Lillard was now available, and the NBA offseason was off to the races. Wojnarowski reported on July 4 that Portland was “open for business” across the NBA and in “no rush” to do a deal with Miami despite Lillard’s preference to go there. Totally normal stuff. 

Then the game of leak and manipulate began. ESPN published a bizarre news column from Wojnarowski that doubled as a profile of Trail Blazers executive Joe Cronin. The piece began very definitively: “Cronin doesn’t plan to operate a transfer portal to the Miami Heat and dutifully deliver history’s greatest Blazer to his targeted team.”

Wojnarowski also reported on tactics from Goodwin to depress the market outside of Miami. Those threats would later be investigated by the NBA.

Altogether, Wojnarowski was very clear in his perspective on the deal:

“That’s how Miami can still end up landing Lillard. Hang around, wait out the muddled uncertainty of the process and hope the dog days of the summer offseason eat away at rivals’ ambitions. Without a trade, Portland can always bring Lillard back for the start of September training camp.”

Lillard to Miami was a last resort. An unlikely failure.

Out in South Florida, veteran podcast host Dan Le Batard shared Miami brass’s view that Wojnarowski was “bought and paid for” by Portland. Cohost Amin Elhassan claimed the trade was “done” and jeered Wojnarowski for indicating otherwise. If the profile of Cronin wasn’t enough, there’s also the fact that longtime Wojnarowski partner Mike Schmitz left ESPN to join Portland’s front office last year.

By the time Lillard was traded this week, NBA fans suddenly heard that Goodwin made it known earlier in September that Lillard would accept a deal to Brooklyn or Milwaukee in place of the on-the-outs Heat. Miami apparently never prioritized acquiring Lillard to the degree many assumed. And the Toronto Raptors were either on the cusp of acquiring Lillard or just a stocking horse in negotiations, depending on which talking head was on your screen at the time.

No matter your NBA allegiance or your views on player empowerment, the situation highlighted just how fundamentally unique the NBA transaction game has become. And that while Silver may decry the state of affairs when stars like Lillard make things ugly with their teams despite lengthy contracts on the books, the media is just as enveloped in the whole process as players, teams or agents.

Let’s go back to the previous two inflection points. When James left Cleveland for South Beach, he blew the top off of how player movement worked in the NBA. Suddenly, any destination and any price was on the table. His return to Cleveland four years later featured a secret Sports Illustrated Op-Ed and fans tracking airplanes. When James went to the Lakers four years after that, many in NBA media considered it an open secret for a year-plus beforehand.

When Wojnarowski arrived at ESPN, the network’s approach to coverage of its partner in the NBA changed completely. Gone was the data visualization, longform storytelling and innovative audio of TrueHoop and ESPN The Magazine. In was the age of the insider. Outlets including The Athletic (with Shams Charania), Turner (with Chris Haynes) and even the New York Times (with Marc Stein) followed suit. Wojnarowski now reportedly makes between $7-$10 million per year at ESPN.

When you combine those two forces you arrive at a crossroads where inevitably insiders are part of the stories they report on.

A league partner (ESPN) pays its primary reporter on the league (Woj) a whopping 8 figures to, effectively, be the primary source of information about a saga (the Lillard sweepstakes) that can be shucked for content all summer long. It is invariably in that reporter’s best interest to control the information flow directly. That way, their TV hits and paywalled articles and social media posts are worth that much more.

As Jesse Pantuosco wrote for Awful Announcing this summer, “Wojnarowski is more a politician than a journalist, making inroads with league power-brokers by any means necessary.” If a reporter’s primary value to his employer is to be first on a story, why should that reporter not be selective with kernels of news that might give other reporters a lead, or cause someone involved in the story to act differently?

In a separate piece on this site, Michael Grant laid bare what that dynamic means: Though many began their careers at local newspapers, today’s sports insiders “could not exist in print journalism.”

Goodwin and Lillard’s approaches highlight a different branch of how basketball media works in 2023. The investigation and warning generated by the NBA around Lillard’s threat not to report to camp anywhere besides Miami came because Goodwin leaked that threat directly to local Heat reporters. Goodwin fed the news appetite around the NBA’s biggest story by delivering something salacious. As we know now, it wasn’t entirely true. Lillard has already announced his excitement to play with Giannis Antetokounmpo and the Bucks.

But Goodwin got what he wanted (depressing the trade offers outside of Miami) by making it known around the league just how ugly he and Lillard would make it if the Blazers didn’t play ball. And he found reporters who would go along with him; he gave them their chance to compete in the news-breaking game.

This  is why the NBA is unique. And why this saga marks another inflection point in the league.

At a time, as Wojnarowski’s July article explained, in which trades are the primary means of player movement as opposed to James’ free agency odyssey, the game has changed. It’s no longer just about numbers and years on a new contract. Leverage and negotiations are vital. Which means insiders are not just valuable to their employers who put out content, but also to a trade’s stakeholders themselves.

CHARLOTTE, NC – JANUARY 18: Damian Lillard #0 of the Portland Trail Blazers reacts after a play during their game against the Charlotte Hornets at Spectrum Center on January 18, 2017 in Charlotte, North Carolina. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Streeter Lecka/Getty Images)

Why did NBA fans not know Miami had deprioritized a Lillard trade as the summer progressed? How, despite so much reporting on these negotiations, did fans never hear of Lillard’s acquiescence to Brooklyn and Milwaukee until after the fact?

The details that mattered in the final days of the Lillard sweepstakes were that Portland refused to talk with Miami, that the Heat moved on, and that Lillard changed his tune on where he would report.

It’s been said the NBA has successfully turned itself into a year-round sport. The league has been lauded for doing so. But in the 24/7 NBA of 2023, the only news fans receive is what’s been filtered to them. In large part, it’s hardly news at all. It’s a manufactured morsel designed to recalibrate negotiations in a very particular way.

And only a select few — the executives in question, the networks cooking up those morsels, and the insiders getting fat paychecks — really benefit.

About Brendon Kleen

Brendon is a Media Commentary staff writer at Awful Announcing. He has also covered basketball and sports business at Front Office Sports, SB Nation, Uproxx and more.