What do the Blazers owe Lillard? He is their all-time scoring champion and arguably the best player in the team's history. In his 11 seasons with Portland, he signed three contract extensions and always insisted he wanted to lead the team to its first championship since 1977.
For Lillard, who turns 33 this month, he said in April that he wanted "a chance to fight for a championship". He and the team seemed to agree at the time, but when Portland got a prospect in the draft draw and the team didn't trade for other stars, they used the prospect to select 19-year-old point guard Scott Henderson. The Trail Blazers also couldn't make any major roster updates in free agency, so he asked to be traded to the Heat.
For Portland, Lillard owes nothing to the city he loves. If Cronin "lacks emotion" (as ESPN interviewed by team executives), then he's just doing his job. Even if he wants to send Lillard to Miami, he has a responsibility to make decisions that are in the team's long-term interest. To get the best trade return from the Heat, the Trail Blazers need to take advantage of offers from other teams. If Miami doesn't already offer everything possible, Lillard's strategy of "just going to the Heat and not other cities" could backfire.
On this point: ESPN notes that Miami could offer first-round picks for 2028 and 2030, plus five first-round swaps, 2022 rookie Nikola Jovic and this year's draft Jamie Jax, provided they wait until July 31 to execute the trade. Here are some additional options for the Heat:
- If the Oklahoma City City agrees to remove Miami's protection of the 2025 pick, the Heat could offer three first-rounders instead of two. The pick is a top 14 pick in 2025 and becomes an unprotected first round in 2026.
- If the Heat modify the pick so that it becomes an unprotected 2026 first-round pick, then they can offer three (2024, 2028, and 2030) picks unprotected and three first-round swaps (2025, 2027, 2029).
- Miami could also trade its 2029 and 2030 second-round picks, as well as its 2026 second-round picks.
- Even if you pull a third-party team and add Hiro to the trade, you may bargain over the rest of the trade. Are the Heat willing to give up Caleb Martin? Will they bring back Yusuf Nurkic from Portland? Will Kyle Lowry or Duncan Robinson get involved?
The best-case scenario for the Trail Blazers is that a trade with the Heat will bring them several rotation players on rookie contracts, three first-round picks, three first-round swaps, three second-round picks, and a plug-and-play base-salary contract (Martin). That might be enough, as not so many teams want to pay Lillard more than $60 million when he is 36, and Portland won't let the team rebuild from scratch, Sharp and Anfini Simmons will stay on the team.
However, it wasn't a surefire deal, as the Minnesota Timberwolves did last summer to get Rudy Gobert. It's entirely possible that the Trail Blazers will find a better solution elsewhere.
The day the Houston Rockets met James Harden's trade request, owner Tillman Fertita asked him if you wanted to go to Brooklyn or Philadelphia. If the Trail Blazers are weighing two equally acceptable offers to Lillard, it makes sense to ask him the same questions. However, there is no guarantee that they will be in a relationship like the Rockets and Harden, nor is there any guarantee that one of the two teams will be the Heat. It's worth remembering that despite Harden's very strong relationship with the Rockets, they didn't close the deal until a few weeks after the start of the season, but the already awkward situation has become untenable. Even though everyone involved wants to move things forward quickly and cleanly, that's not always the case.
In 2017, then-Cavaliers general manager David Griffin compared the addition of LeBron James to his team to be responsible for Babe Ruth's legacy. "It's almost like the divine trust this kid gave you," Griffin said at the time. "He's brilliant in his own right, and he in a way demands that you have to be a title contender just by his presence... If you don't take advantage of his peak, then it will put us to shame. Building the team around Lillard proved more difficult, but the motivation was the same: He trusted Portland's management, but the team failed to make him a championship contender.
However, James repeatedly signed short-term contracts to put pressure on Cleveland management. If the squad isn't strong enough, he's not far from being a free agent. Lillard signed a two-year, $122 million contract extension last summer that will allow him to become a free agent by the end of the 2023-24 season. By renewing his contract, Lillard also quelled outside noise about whether he would remain with the Blazers, but he eventually waived the veto power over a trade that would affect his trade.
Until Lillard makes a trade request, it's incumbent on the Blazers to try and build a championship-caliber team with him at its core. However, that doesn't mean seeking immediate promotion at all costs (i.e. trading potential stars for non-star veterans), so Lillard's dissatisfaction with the team's offseason performance is entirely understandable.
Now that Lillard has filed his trade application, the Trail Blazers should find a deal for him that gives him a chance to win a championship and set him up for the post-Lillard era. But that doesn't mean they have to trade him on his terms. They only have one chance to close the deal, so if Miami hasn't made a better offer for the deal, they have a responsibility to accept the better offer.