It was hard to believe at the time and it's even harder to believe now, but it's true: There was a loud, pretty big contingent of people -- largely comprised of South Florida homers but people from all over got behind the radical cause -- who adamantly believed that Joe Cronin, and by extension, the Trail Blazers, either owed it to Damian Lillard to send him to Miami, or specifically didn't out of spite.
You people were always wrong. The Blazers didn't owe Lillard anything beyond the hundreds of millions of dollars they have paid him, and they didn't trade him to Milwaukee to spite Miami. Damian Lillard plays for the Bucks now because they had the best offer.
Loads of reporting, as usual, has come out in the wake of this deal. Much of it is pretty one-sided stuff so take it for whatever you feel it's worth. For my money, the whole saga was perfectly summed up by Adrian Wojnarowski, who penned the following for ESPN:
Cronin talked to his staff about controlling the tempo of the talks, slowing the process and using July and August to explore the marketplace. He studied the trade models of Brooklyn's Sean Marks with Durant, and Philadelphia's Daryl Morey with Ben Simmons. In those acrimonious showdowns, patience had been the pathway to incrementally increasing offers.
Cronin's peers, who had been in these circumstances, privately told him what he had publicly declared: His obligation was to find the best deal for the Blazers, not for Lillard. If those conflicting elements matched up, even better for everyone.
Through it all, Cronin told himself: Eliminate the emotion, the frustration, the fatigue. And most of all, Cronin implored himself: Don't settle. Don't let yourself settle.
Suffice it to say, Cronin did not settle. All told, when factoring in the initial return for Lillard and subsequent flipping of Jrue Holiday to the Celtics, this is the haul Portland has put in the bank:
Here’s the Damian Lillard return in Portland:— Bobby Marks (@BobbyMarks42) October 1, 2023
2024 GSW first (top 4 protected)
2028 Milwaukee pick swap
2029 Milwaukee unprotected first
2029 Boston unprotected first
2030 Milwaukee pick swap
All of this, and Cronin also managed to finally get off Jusuf Nurkic. And he probably isn't done yet. He's got his perimeter foundation set with Scoot Henderson, Shaedon Sharpe and Anfernee Simons, making Malcolm Brogdon expendable. If he's healthy, he could net another first-round pick.
If Robert Williams III can stay healthy, he is a massive score to pair with Henderson and Sharpe. For all the hate thrown at Deandre Ayton, he's a super-skilled, 25-year-old 18-and-10 big with proven deep-playoff value. Those three Milwaukee picks/swaps have a chance to become significant assets when the Lillard-Khris Middleton-Brook Lopez triumvirate ages out and Giannis Antetokounmpo, as a result, potentially relocates.
Two more picks from the Holiday flip, and that's five first-rounders or swaps, and maybe six if Brogdon is moved. The Golden State and Boston picks will likely be late firsts, but the same can be said of the picks Miami would've sent to Portland. The big score is Portland effectively taking over Milwaukee's future draft capital in a potential post-Giannis era, and being able to flip Holiday, who obviously holds way more market value than Tyler Herro.
In other words, just be quiet, Heat homers. Cronin played this perfectly, and in doing so, in my eyes, he's already locked up executive of the year. I mean, on top of all the future assets he banked, the guy drafted what could be an All-NBA point guard in Henderson and still has a team that can actually compete while Henderson and Sharpe continue to develop.
Indeed, the Blazers look like last year's Jazz, who filled their war chest with Donovan Mitchell and Rudy Gobert trades while also putting a surprisingly competitive team on the floor. Look at the top of the Blazers' roster: Henderson, Sharpe, Simons, Jerami Grant, Ayton, Williams, Brogdon, Matisse Thybulle and Kris Murray.
So now Henderson doesn't have to come along in a losing environment. Perhaps Grant gets traded for more assets. Simons, I would think, is a possibility to be moved for more capital as well, as the Blazers know full well the challenge of building around a small backcourt.
You start adding all this up, and it's just incredible work by Cronin and his staff. They patiently navigated a situation that could've easily backed them into a corner. And in the end, they still did right by Lillard by sending him to a ready-made title contender to play with one of the three best payers in the world.
So yes, the executive of the year race is over. Just give the hardware to Cronin. He earned it.