Trail Blazers Can't Afford to Mess Up Damian Lillard Trade
If Joe Cronin is truly prioritizing the future of the franchise, he has to be prepared to send Lillard somewhere other than his preferred destination of Miami.
This is a big spot Joe Cronin is in. The biggest since he took over as the Trail Blazers' general manager 18 months ago.
As a GM, you never want to be in a position where you have to trade a player as good, or that has meant as much to your franchise and city, as Damian Lillard. And when you're forced to, it's a decision you can't mess up.
By now, everyone knows the situation. Cronin talked at every turn over the past year about wanting to make aggressive upgrades around Lillard to build a contender. He hasn't been able to deliver on those promises and instead drafted a point guard with the No. 3 overall pick in the draft; because of that, Lillard officially requested a trade over the weekend.
Lillard and his representatives have left no doubt that the only place he wants to be traded is Miami. The Heat have a package to offer that can charitably be described as "uninspiring." So, there's a problem.
How Cronin navigates that problem, and if he's truly willing to make a deal with another team for a better return despite an escalating, increasingly public negotiation, will determine whether the post-Lillard era of the franchise under his watch will be more successful than the last two seasons have been.
It's telling that even those advocating for the Blazers to trade Lillard to Miami aren't trying to convince anyone that their best possible offer is halfway acceptable for a player of his stature.
The Heat can only offer two first-round picks, in 2028 and 2030, and they aren't a franchise it's wise to bet on ever being in the lottery (it's happened four times in the last two decades and just six times since Pat Riley joined the organization in 1995). The two young prospects they can offer, Nikola Jovic and No. 18 overall pick Jaime Jaquez Jr., don't profile as high-end starters. Duncan Robinson and Tyler Herro are negative-value contracts, and Herro plays the same position as the three players Portland would be rebuilding around. There's been talk of rerouting Herro to a third team, but that's likely not going to bring more good assets back to Portland.
The only argument in favor of making that deal is that Lillard wants to go to Miami and the Blazers should send him where he wants to go as a thank-you for the last 11 years. For better or worse, Cronin's actions over the past year have shown that doing what's best for the franchise's long-term future is a higher priority for him than doing what's best for Lillard. In the days since the trade request, Cronin’s words have caught up to that, too, starting with the terse statement he issued that day that he planned to "do what's best for the team."
If that's the stance Cronin is going to take publicly—and, to be clear, it's the right stance to take at this moment—he has to be prepared to follow through on it more than he followed through on his promises to build a contender around Lillard.
Cronin has not played this situation well since the trade deadline, at least from a public messaging standpoint. But he's played it exactly right since Lillard actually requested a trade on Saturday. He's put the word out to teams that he's willing to take offers outside of Miami and isn't afraid to potentially send Lillard somewhere else if he gets a deal he likes more.
Just like he didn't give away the third pick for a sub-superstar-level player like Brandon Ingram or Zach LaVine, Cronin can't afford to give Lillard away to the Heat. So far, he's signaling that he's not going to. If he holds to that, he has the chance to redefine how he's viewed in a job he's still relatively new to.
No matter how this goes, Cronin is going to be the bad guy in a lot of people’s eyes. He was the GM that repeatedly and publicly promised to go all-in to build around the greatest player in franchise history and then was unable to do so and led Lillard to request a trade. This is not a PR battle he's going to win, no matter what deal he eventually makes. But he can't be the GM who lost Lillard and got back arguably the worst return for a star since Memphis' infamous Pau Gasol trade to the Lakers in 2008.
The argument that the Blazers sending Lillard somewhere other than his preferred destination will make other players not want to sign in Portland doesn't really hold water, either, and scans more as a negotiating tactic than a serious position. Publicly, it isn't landing the way Lillard's representatives thought it would.
The Pacers' reputation has not been destroyed in the years since they traded Paul George to Oklahoma City in 2017 after he'd made it clear he only wanted to go to the Lakers. George even ended up re-signing with the Thunder a year later. Jazz president Danny Ainge traded Donovan Mitchell to Cleveland, not his preferred destination of New York, a year ago and hasn't found himself blacklisted by players and agents. The Spurs have been fine since they traded Kawhi Leonard to Toronto rather than the Lakers in 2018.
Indiana, San Antonio and Utah aren't the kinds of markets that have stars lining up to play there any more than Portland is. The only chance franchises in their position have of being competitive is by drafting well and by not getting cleaned out when they do have to make trades like this. Even with Scoot Henderson and Shaedon Sharpe as a pretty enviable starting point for a rebuild, it will be hard for Cronin to recover from trading Lillard to Miami for pennies on the dollar.
Maybe we've all had Lillard figured out wrong for 11 years, and he would actually be willing to hold out and turn this into a James Harden-Ben Simmons spectacle if he's traded somewhere other than Miami. As someone who knows him well and has covered him for years, I have a hard time believing it would go that way. Lillard is more Kevin Durant than he is Simmons—he loves to play basketball more than anything, and will show up and talk himself into a good basketball situation, even if it's not Miami. The true heel turn it would take to blow that up is simply not in his nature, as much as those close to him are acting currently like it's a possibility.
Nearly five years ago, when Anthony Davis asked to be traded from New Orleans during the 2018-19 season and made it known he wanted to be a Laker, I wrote that other teams (including the Blazers) should still make offers despite not knowing if he wanted to play for them, just like Sam Presti did for George and Masai Ujiri did for Leonard. Both George and Leonard only had one year left on their deals when they were traded; Lillard has at least three, plus a $63 million player option he'll probably pick up.
Ironically, for the right team, trading for Lillard could be exactly the kind of push-all-their-chips-in swing that he always wanted the Blazers to take for him but they never did under either the current or previous front office. The kind of swing that would have prevented Lillard from asking out.
If Cronin wasn't willing to do that for Lillard in the past six months because he was prioritizing the future, he can prioritize the future above all else in a Lillard trade, too. And if Lillard wants out of Portland simply for a better chance to win, there have to be other places than Miami that can give him that.
A trade to the Heat, for the return they can offer, as the only option won't make either side in this divorce look good.