There's one nightmare scenario the Portland Trail Blazers must proactively avoid at all costs to fully maximize their return from the blockbuster Damian Lillard deal. If their protected first-round pick conveys to the Chicago Bulls in 2028, the Trail Blazers would lose the ability to use the Milwaukee Bucks' 2028 swap rights because, well, they'd have no pick to swap.
That would ruin a significant part of the Trail Blazers' Lillard trade. It's even more critical that they do everything they can to avoid this outcome now that Milwaukee's roster is hanging on by a thread. Any external additions like Kyle Kuzma were just band-aid solutions, but this Bucks roster is badly wounded and needs far more than that.
Blazers must make sure they can actually cash in on Bucks’ downfall
Lillard's heartbreaking Achilles tear could force him to miss the entirety of the 2025-26 season, and, unfortunately, who knows if he'll even return as the same player at 35. Brook Lopez's production continues to decline as he's now 37 years old, and he may be somewhere else entirely by the start of next season as he's set to hit free agency.
For the first time in his career, Giannis Antetokounmpo is open to the idea of playing elsewhere. It could be in the best interest of both Giannis and the Bucks' organization to hit the reset button. And teams like the New Orleans Pelicans and Trail Blazers are set to benefit.
Not because they are in the Giannis sweepstakes themselves, but because they have Milwaukee's future picks that only continue to increase in value with each development (and the offseason hasn't even officially started yet).
It's becoming increasingly likely that Portland will use Milwaukee's 2028 pick swap as the two teams are trending in opposite directions.
Rip City is looking to end its four-year playoff drought as soon as next season. Still, having aspirations and actually getting there are two very different things. And the harsh reality is the Trail Blazers might be further from that goal than they realize.
They are showing promising internal improvement, but the gap between them and the rest of the Western Conference hasn't drastically changed. Two lottery teams that will be in the playoff conversation are the San Antonio Spurs and Dallas Mavericks, who are loaded with talent, getting healthier, and somehow adding the top two 2025 draft picks to their rosters.
Whether or not the Trail Blazers make the postseason determines their draft capital, as Portland owes Chicago a first-round pick as part of the questionable Larry Nance Jr. trade. That pick is lottery-protected up until 2028 and will turn into Portland's 2028 second-round pick if it is not conveyed before then.
So if the Trail Blazers miss out on the playoffs until 2028 but make it that season, their pick is headed to Chicago. And to make matters worse, they wouldn't be able to swap with Milwaukee.
The good news is that this is a very specific outcome, and odds are they avoid this regardless. But it's still imperative that the Trail Blazers keep this in mind. They should proactively try to prevent this nightmare scenario, and there are a few routes to take.
Portland could renegotiate the pick they owe to Chicago, conveying it earlier or getting it back entirely. They could also trade away the Bucks' draft swap, which may not have as much value if they hold onto it, as Milwaukee would have more incentive to remain competitive at that point.
Or, in the best-case scenario, they make the playoffs next season, and this all goes away.