But if Antetokounmpo hadn’t signed his super-max extension, maybe he could have gone to Portland.
If Giannis were to leave Milwaukee – I’m talking about this past summer, before signing the extension. If the team didn’t make the necessary moves to make Giannis feel comfortable, I believe there was a team that he would have considered leaving for. And that team is the Portland Trail Blazers.
Sources have told me that Giannis and Damian Lillard, they’ve gotten really close over the last few months. And they were talking about working out together. And I want to explain how important that is to people out there. Giannis doesn’t work out with anybody that’s not on his team. He doesn’t do that. He’s turned down working out with LeBron James and turned down being part of the Space Jam 2 movie. He doesn’t do that. Him and Dame were supposed to work out.
Sources have told me both them were talking with each other about the possibility of what it would look like playing with each other when their contract allowed so. I believe Dame was trying to tell Giannis about what it would look like, him playing in Portland. And same vice versa, Giannis trying to tell him what it’d be like playing in Milwaukee.
The workout never happened between Dame and Giannis, obviously, because the NBA came sooner than what everybody expected.
Stars talk about teaming up far more often than they actually team up.
In this case, it’s tough to get past the question of: Where? Lillard was locked into Portland far longer. But Antetokounmpo obviously wasn’t ready to leave Milwaukee. As much as Lillard and Antetokounmpo hold similar sensibilities and could work well together, their shared approach makes it difficult to see one leaving his current team for the other’s.
Innocuous comments could also easily get misconstrued. Antetokounmpo is so averse to working out with other stars, it was news when he said he was open to teaming up with another superstar in Milwaukee. Antetokounmpo merely planning to work out with Lillard could get viewed as something bigger than it really was.
It’s also worth noting Portland would have had to clear significant depth to make room for Antetokounmpo. The Trail Blazers could’ve unloaded C.J. McCollum ($30,864,198 salary next season), Jusuf Nurkic ($4 million of $12 million guaranteed), waived Rodney Hood ($10,851,246 unguaranteed salary) and renounced restricted free agent Zach Collins… and still not have had max cap space for Antetokounmpo. Portland could’ve made other moves to open max cap room or executed a sign-and-trade. But the point stands: Antetokounmpo would’ve joined a stripped-down version of Trail Blazers, not simply added to the group we see.
Of course, this is all moot with Antetokounmpo signing his extension. But it’s a fun “what if?”.