After managing to bring back all three of Nikola Vucevic, Coby White, and Andre Drummond as well as signing a very solid role player in Jevon Carter, the early days of free agency appeared to be going swell for the Chicago Bulls. That good luck was bound to run out eventually, but I never would have guessed a trade request from Damian Lillard would bring the good vibes to an end.
The Athletic’s Shams Charania confirmed the suspicions swirling around the rumor mill, specifying that Lillard desires to be dealt specifically to the Miami Heat, to join Jimmy Butler and Bam Adebayo in pursuit of a championship. Any deal for Lillard is likely to include a package of Tyler Herro, role players, and draft picks.
Lillard joining up with Miami (or Brooklyn, another destination he previously mentioned would be desirable) would just make things even more difficult for the Bulls. Already a fringe playoff team, it would be extremely difficult to sell Chicago as a true contender when the Bucks, Celtics, 76ers, and Dame-led Heat stand in the way.
If Damian Lillard is dealt to an Eastern Conference contender, the Chicago Bulls will inadvertently suffer greatly.
But this wouldn’t even be the worst part for the Bulls, as they stand to lose even more in the way of draft capital. In 2021, Chicago traded away Lauri Markkanen in exchange for Derrick Jones Jr. and a lottery-protected first-round pick from the Trail Blazers. The assumption was that Portland would immediately make the playoffs and the pick would convey, but injuries have held Lillard and the Blazers back the last two seasons as they’ve limped into the draft lottery.
Now, the Bulls find themselves on precarious footing if the Trail Blazers intend to initiate a full-blown rebuild. By trading Lillard, it can be assumed that Portland would look to reshape the roster around No. 3 overall pick Scoot Henderson and spend the next few years prioritizing accumulating young talent rather than winning basketball games.
Chicago can’t just wait this out, unfortunately. If Portland’s first-round pick does not convey to the Bulls by 2028, it instead becomes a second-round pick. That would be nothing short of disastrous. We’re still five full seasons out from that occurring, but we’ve seen small-market rebuilds last much longer than that before.
However, there might yet be some light at the end of the tunnel for the Bulls, even if Portland decides to move Dame. As foolish as it might sound, Trail Blazers’ GM insists they remain committed to winning now by inking Jerami Grant to a $160 million extension. This is only re-affirmed by the rumor that the Blazers are looking for star-level talent in return for Lillard, rather than a package of young assets and picks.
It’s still far too early to tell just how things will shake out, but no matter which way you cut it, Dame’s trade request is nothing but bad news for the Bulls. An additional mid-first-round draft pick would have provided the Bulls with much more flexibility in building this roster (and potentially kickstarting the rebuild), but now it seems Chicago may have given up their All-Star lottery pick Markkanen for nothing.