Damian Lillard and Jrue Holiday Secure a Massive Haul for the Blazers, and Joe Cronin Clinches Executive of the Year
At the time, and even now, it’s almost unbelievable. There was a vocal contingent, primarily comprising South Florida enthusiasts but with supporters from all corners, who fervently believed that Joe Cronin, and by extension, the Portland Trail Blazers, either owed it to Damian Lillard to ship him off to Miami or, conversely, deliberately refused to do so out of spite.
However, let’s set the record straight – those claims were unequivocally wrong. The Blazers did not owe Lillard anything beyond the hundreds of millions of dollars they’d already invested in him, nor did they trade him to Milwaukee out of any animosity toward Miami. The truth is, Damian Lillard now dons a Milwaukee Bucks jersey because they presented the most compelling trade offer.
In the aftermath of this momentous deal, a plethora of reports and analyses have inundated the media, often with a biased slant. For my part, the entire saga was succinctly encapsulated by ESPN’s Adrian Wojnarowski, who articulated the following:
Cronin deliberated with his team on the negotiation strategy, opting for a slower, more methodical approach during July and August to explore the trade market thoroughly. He took inspiration from trade models like Sean Marks’ dealings with Kevin Durant in Brooklyn and Daryl Morey’s handling of Ben Simmons in Philadelphia. In those intense negotiations, it was patience that led to progressively improved offers.
Cronin’s peers, who had found themselves in similar circumstances, privately advised him on what he had openly declared: his responsibility was to secure the best deal for the Blazers, not necessarily for Lillard. If the stars aligned and these interests converged, it was a win for everyone involved.
Throughout the process, Cronin continuously reminded himself to eliminate emotional factors, frustration, and fatigue. Above all, he implored himself: do not settle. Do not allow compromise.
It’s safe to say that Joe Cronin did not settle. When considering the initial return for Lillard and the subsequent trade of Jrue Holiday to the Celtics, the benefits reaped by the Portland Trail Blazers are nothing short of impressive:
Here’s what the Damian Lillard trade has brought to Portland:
- Deandre Ayton
- Malcolm Brogdon
- Robert Williams
- Toumani Camara
- 2024 Golden State Warriors first-round pick (top 4 protected)
- 2028 Milwaukee pick swap
- 2029 Milwaukee unprotected first-round pick
- 2029 Boston unprotected first-round pick
- 2030 Milwaukee pick swap
(Bobby Marks @BobbyMarks42, October 1, 2023)
Furthermore, Joe Cronin managed to shed the burden of Jusuf Nurkic, and it appears he’s not finished yet. With a solid perimeter foundation featuring Scoot Henderson, Shaedon Sharpe, and Anfernee Simons, Malcolm Brogdon could be considered expendable if he returns to full health, potentially yielding another first-round pick.
Should Robert Williams III maintain his health, he could be a tremendous asset to complement Henderson and Sharpe. Despite the criticism Deandre Ayton has faced, he’s an extraordinarily skilled 25-year-old big man who consistently produces 18-and-10 stats and has proven his value in deep playoff runs. The three Milwaukee picks/swaps hold great potential as significant assets, especially as the triumvirate of Damian Lillard, Khris Middleton, and Brook Lopez ages, possibly leading to Giannis Antetokounmpo’s relocation.
Add the two additional picks from the Jrue Holiday trade, and the Blazers have secured five first-round picks or swaps, perhaps six if Brogdon is moved. While the Golden State and Boston picks may land late in the first round, the same can be said of the picks that Miami would have sent to Portland. The grand achievement here is Portland’s effective acquisition of Milwaukee’s future draft capital, especially considering a post-Giannis era, and their ability to flip Holiday, who holds a higher market value than Tyler Herro.
In essence, Miami enthusiasts should heed a piece of advice: stay quiet. Joe Cronin played his cards masterfully, and in my view, he has already secured the title of Executive of the Year. Not only did he accumulate a wealth of future assets, but he also drafted a potential All-NBA point guard in Henderson while maintaining a competitive team during his development.
The Portland Trail Blazers now resemble last year’s Utah Jazz, who stockpiled assets through trades involving Donovan Mitchell and Rudy Gobert while fielding a surprisingly competitive team. Survey the top of the Blazers’ roster: Henderson, Sharpe, Simons, Jerami Grant, Ayton, Williams, Brogdon, Matisse Thybulle, and Kris Murray.
With Henderson no longer confined to a losing environment, the possibility of trading Grant for more assets becomes apparent. Simons might also be on the move as the Blazers recognize the challenges of building around a diminutive backcourt.
When you add all of this up, it’s an extraordinary feat by Joe Cronin and his team. They navigated a situation that could have easily cornered them into making less favorable decisions. And in the end, they did right by Damian Lillard by sending him to a ready-made title contender, where he will play alongside one of the world’s top three players.
In summary, the race for Executive of the Year has concluded, and the hardware rightfully belongs to Joe Cronin. He earned it.
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