Quick: Damian Lillard’s trade request, a long-time coming, marks the end of an era. It also offers resolution

Damian Lillard was traded to the Milwaukee Bucks on Sept. 27 in a three-team trade. Sign up for The Bounce to get basketball content delivered straight to your inbox.

PORTLAND, Ore. — The lowest of lows for Damian Lillard was in the summer of 2021, on the heels of an embarrassing playoff loss to the Denver Nuggets. In the nights that followed the first-round exit, he said he couldn’t sleep. His insomnia wasn’t because he was eliminated by a Nuggets backcourt that started Facundo Campazzo and Austin Rivers, it was because he questioned if the people around him in the Blazers organization cared about the loss as much as he did.

That summer triggered a switch in Lillard. Suddenly, it seemed, an organization that did everything for him — his approval and opinion were sought on everything from player moves and coaching hires, to practice times and plane departures — wasn’t doing enough.

So he began to voice his displeasure, first internally and then publicly, albeit in ways that would allow Lillard to proclaim no one ever heard it from his mouth, thus protecting him from backlash. He felt the Blazers should have been giving him more help with the roster, a feeling that only heightened that summer as he watched P.J. Tucker win a ring with the Milwaukee Bucks in July 2021.

In 2020, Lillard thought the Blazers had an inside track to luring Tucker away from the Houston Rockets. Carmelo Anthony, then with the Blazers, had been in frequent contact with Tucker and was convinced Tucker would be on board with joining the Blazers. So, Lillard went to then-Blazers general manager Neil Olshey and asked him to make it happen.

Instead, Olshey traded for Trevor Ariza, who was solid but was of no help in the playoffs later that 2020 season when he chose not to participate in the NBA Bubble. To Lillard, it was another wasted opportunity.

So as much as Lillard has been proclaiming that he wants to stay in Portland, his trade request on Saturday has been a long time coming. It appears the final straw may have come last week, when Blazers general manager Joe Cronin didn’t follow through on his goal to build a win-now product around Lillard. Armed with the third pick, the 23rd pick and a young 20-point scorer in Anfernee Simons, Cronin not only didn’t make a trade to bring in veteran help, but also drafted Lillard’s heir apparent in Scoot Henderson.

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There will be some who are disappointed with Lillard for asking out. Far more will blame the Blazers for fumbling the most prolific offensive player in franchise history because of inactivity. I don’t know that either is to blame. Lillard has earned the right to ask out if that’s what pleases him, I think the majority of Blazers fans will wish him the best and hope he wins that coveted title. But I don’t get this idea that the Blazers never tried to help build a winner around him.

The Blazers have always wanted to do right by Lillard. They gave him input on every decision except the draft. Not a move was made by the Blazers that wasn’t endorsed by Lillard. He was on board with free agent decisions (Evan Turner, Ben McLemore, Gary Payton II), with trades (Jusuf Nurkić, Rodney Hood, Enes Kanter, Norman Powell, Robert Covington, Jerami Grant) and he agreed the team should welcome Melo. And for two seasons, Portland even went as far as to use a roster spot for his cousin, Keljin Blevins.

Portland also had some terrible injury luck during his run. Wesley Matthews blew out his Achilles in March 2015 when Portland had the West’s third-best record. Nurkić broke his leg in March 2019, the year the Blazers went to the Western Conference finals. And Zach Collins had shoulder problems, then ankle surgeries right when he inherited the starting power forward spot. Now healthy in San Antonio, Collins looks poised for an impactful career.

There was hope that Lillard had found a connection with the new general manager. They spoke often. They said they shared the same vision. And in April, during his session with the media after the season finale, Lillard practically boasted that he knew of players who wanted to come to Portland, players who could “move the needle.” It wasn’t the first time Lillard was under the illusion players were lining up to play with him, and it wasn’t the first time he felt the front office didn’t follow through. But we now know it wasn’t just Olshey who couldn’t somehow land these big fish to appease Lillard.

This is not to say who is right and who is wrong in all of this. It’s mostly to illustrate why all of this is so disappointing. The Blazers and Lillard were so perfect for each other. Much like Portland, Lillard considers himself an underdog. He was benched in high school. Was so lightly recruited he ended up at Weber State. Portland has long carried the grudge that it is disadvantaged as a small market, and gets unfair treatment from referees and national media coverage. The Portland community didn’t just relate to Lillard, they loved him and his story, and when he loved Portland back? It was powerful stuff.

Even with new blood up and down the organizational ladder — new owner, new president, new general manager, new coach — the franchise was in consensus that they wanted Lillard and should build around him. So it’s disappointing that with all that braintrust, and all that love that they couldn’t find the right communication, the right plan, or the acceptable followthrough to make it happen.

And mostly, it’s disappointing Blazers fans have to go through this divorce. This fan base loved Lillard like no other player. There can be a debate about whether Lillard tops Clyde Drexler or Bill Walton as the greatest Blazer of all time, but there is no debate about which player most gripped this region’s heart. It was Lillard. He hit two of the most memorable shots in franchise history — the 0.9 dagger to eliminate Houston in 2014 and the wave-bye-bye 3 to eliminate Oklahoma City in 2019 — and he poured himself into the community more frequently and passionately than any other Blazers star. He was intimately involved with Special Olympics, and his RESPECT project with Portland-area high schools wasn’t just for show, he was actively involved. He spoke at assemblies, promoted students on social media, all while amplifying his message for students to show up, work hard and be kind.

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He was everything an organization and a fan base could want in a franchise star, and then some.

But things changed.

In 2021, the eight deaths within 18 months to family and those within his inner circle, made him think about his own mortality, which he shared with The Athletic at the time:

“I thought about (not playing), because mentally I was like … I don’t want to say I didn’t care, because I did care,” Lillard said. “But emotionally, I was like, whatever.”

His emotions had been worn thin because, in the past 18 months, it seemed like he had lived a lifetime. In 2020, he was the first to discover the dead body of his cousin and personal chef. An aunt died from cancer. A family friend died of COVID-19. And in the early months of 2021, a cousin was killed in West Oakland.

And then last Thursday, the day before the Lakers game, Lillard learned of the shooting deaths of two people in his inner circle. One was a cousin close enough to Lillard to be at his family’s Thanksgiving dinner in Portland in November. The other was like family — the best friend of perhaps his closest cousin, who was among the first family members to move to Portland when Lillard was drafted by the Trail Blazers in 2012.

“I could be 45,” said the 30-year-old Lillard. “I’ve done seen and been around so much.”

His core injury, which became so bad at the end of 2021 that he ended his season to have it surgically repaired, made him anxious about his professional timeline.

Soon, Lillard became focused on how the Blazers’ organization was falling short, losing sight of what was one of the last, great symbiotic relationships in pro sports. That’s not saying Portland as an organization was perfect. Neither was Dame. And somewhere between the mistakes, both lost sight of what made the other great. Lillard lost sight of how much empowerment and freedom the Blazers gave him. And the Blazers apparently underestimated how seriously and urgently Lillard valued winning at a high level.

I’ll miss him. We all will. But I won’t miss what this relationship with the Blazers had become. The veiled threats of asking for a trade, always under the guise of “you never heard me say it.” And I won’t miss the organization walking on eggshells wondering if he was happy enough. No one player is bigger than the franchise, and if the Blazers weren’t guilty of violating that credo, then they were toeing the line. There were many who were exhausted by it all.

Now, Blazers fans can have a new obsession, a healthier one than worrying about Lillard’s future and what his latest social media post was supposed to mean. The Blazers have started to build a young and exciting core. With the speed and explosion of Scoot Henderson, the soaring of Sharpe, and the shooting of Simons, the Blazers could become one of the most entertaining teams on a nightly basis. I have no idea how they will stop teams, but I bet you will see a couple of plays every game that will make you jump out of your seat. So, they might not win many games. Guess what? Neither have the Blazers teams the past two seasons with Lillard. At least now there is a clear direction, and not some wishy-washy concept of trying to land big-name stars in the name of appeasing Lillard.

In a statement Saturday, Cronin said his stance never wavered: “We have been clear that we want Dame here, but he notified us today he wants out and he’d prefer to play someplace else. What has not changed for us is that we’re committed to winning, and we are going to do what’s best for the team in pursuit of that goal.”

Make no mistake: this is a sad day. An era has ended. The wrist taps. The mean mugs. That string of eight consecutive playoff appearances. All the franchise records — 71 points in a game, the 19,376 career points — all of the buzzer beaters.

He was a breathtakingly exceptional player, and to many behind the scenes within the organization — those who sold tickets, cleaned the gym, ran their promotions — he was just as impactful and thoughtful as a person.

Lillard not only embraced Portland, he gave back to it. That’s a beautiful combination, and one that should have a large say in defining his legacy.

Quick: Damian Lillard’s trade request, a long-time coming, marks the end of an era. It also offers resolution

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