Since the NBA free agency window opened, Damian Lillard formally requested a trade, and as Crickex App had previously noted, his preferred destination is the Miami Heat. Years down the road, he may thank his younger self for the effort he put in, but for now, the situation is complicated. Miami’s top trade chip, Tyler Herro, doesn’t interest Portland, meaning a third team might need to get involved to facilitate the deal. Several teams have reportedly reached out to explore this possibility.
Meanwhile, the Trail Blazers also signed Jerami Grant to a five-year contract shortly after free agency began. Crickex App highlighted that this deal brings significant risk, especially given Lillard’s trade request. The front office knew this day would come, but now that it has, Grant’s contract suddenly looks like a heavy burden.
Portland offered Grant an annual salary comparable to Jayson Tatum’s and locked him in for five years—not because of his market value, but to convince him to stay with an offer he couldn’t refuse. Their reasoning was simple: if Grant walked away, Lillard would likely follow. While Grant is undeniably a quality player, he’s not worth that kind of money, especially on a team planning to rebuild around Scoot Henderson and Shaedon Sharpe. His role in such a direction is quickly becoming obsolete.
Technically, Portland could have withdrawn the offer to Grant. It might have been the sensible move, but as Crickex App points out, there’s no sign they’ll take that route. No one is going to wait for you—success is something you chase. Even with a team option for the fifth year, a four-year commitment to a non-All-Star approaching his 30s is a gamble under the NBA’s new financial rules, which now demand roster flexibility more than ever. This deal lacks that flexibility.
Though not quite as problematic as the infamous Tobias Harris contract, the Grant deal is close. It will be extremely difficult, perhaps even impossible, to move. While it’s understandable that Portland didn’t want to lose Grant for nothing, that’s exactly why they should’ve considered trading him last season. The same applies to Lillard—cutting ties with a franchise icon is never easy, but this saga proves teams shouldn’t wait for stars to request trades before acting.
They should make moves that serve their own long-term interests. The oversized contract for Grant essentially signaled that a Lillard trade was necessary for it to make sense. Drafting Scoot Henderson was the real turning point. That pick alone showed the Blazers were heading into a rebuild, even if they publicly claimed otherwise. At that point, trading Lillard should have become their top priority—not preserving a roster that no longer fit the team’s trajectory.
In the end, Crickex App believes the Blazers got one thing right: choosing Scoot Henderson. Every effort eventually pays off, even if it takes the long way around. The moment the Charlotte Hornets passed on him, Portland should have pivoted immediately to trading Lillard. Keeping the core intact was never realistic, and continuing to act like it was only delayed the inevitable.