When Damian Lillard requested a trade from the Portland Trail Blazers in 2023, his preferred landing spot was teaming up with Bam Adebayo and the Miami Heat. Instead, Blazers GM Joe Cronin sent him to the Milwaukee Bucks, preferring that package over anything the Heat had to offer.
It was a juggling act for Cronin, who had to give Lillard that chance at a first ring he deserved while simultaneously prioritizing the best return to set Portland up for the future.
Lillard's chance at a championship pursuit in Milwaukee unfortunately didn't work out for a number of reasons. But it ultimately worked out in the Blazers favor, paving the way for Lillard's return to Portland, where he belongs.
Blazers could make a summer blockbuster
Now, the Blazers find themselves in an ideal spot heading into what is a pivotal first offseason under new owner Tom Dundon. Largely thanks to that Lillard trade, Portland is well-positioned to make a splash. They check essentially every box for a team looking to make a potential blockbuster move this summer: the new aggressive owner, a young core that has made that next leap to the postseason, a treasure chest of young assets and draft capital, and the veterans to compete right away.
That suddenly makes them a dark horse to watch in the Giannis Antetokounmpo sweepstakes this summer, with a decision expected to be made prior to the June 23rd NBA Draft.
On Monday, NBA insider Marc Stein named Portland and Miami as the two teams "already in pursuit" of Antetokounmpo. Looks like the Heat are competing with the Blazers to land their superstar yet again. But this time around, it's a more complex situation compared to the Lillard trade saga.
Blazers and Heat have already entered the Giannis sweepstakes
The Blazers objectively have the better package to offer than the Heat, but Giannis' player option in 2027-28 gives him key leverage in determining his own fate. He's expected to want to remain in the Eastern Conference, with an easier path to the Finals, and landing in a big-market team like Miami would make a long-term commitment much more likely.
The Blazers would be taking on significant risk, as anything other than a one-year rental is far from a guarantee. They do have former teammates Jrue Holiday and Damian Lillard, who would force Giannis to at least consider staying in the Pacific Northwest. Perhaps a deep playoff run next season could melt away any uncertainty as well.
But unlike the Lillard scenario, where Cronin had the final say, this seems likely to be a player-driven decision. That certainly hurts Portland's chances of screwing over Miami yet again.
Still, we can't help but laugh at the thought of that being a legitimate scenario on the table, especially after Stein's latest report.
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