Damian Lillard's final gift to Milwaukee wasn't a clutch shot or playoff heroics. It was choosing Portland over Boston and inadvertently saving the Eastern Conference from complete chaos in the years ahead.
By returning to the team that drafted him instead of joining the defending champions, Lillard may have performed his most valuable service to the Bucks.
Damian Lillard choosing to go back to the team that drafted him in Portland instead of East rivals in Boston prevented what would have been another terrifying super team assembly.
According to The Athletic, there was reportedly mutual interest between the two, who were already in discussions before Lillard eventually went back to the team that drafted him.
Damian Lillard would have kept the Boston Celtics atop the East
It’s not hard to imagine the nightmare scenario Milwaukee just avoided.
As it is, Boston already holds the league's most complete starting lineup, with elite two-way wings and veteran leadership. Had Lillard gone to Boston, the Celtics could have had a trio of Jayson Tatum, Jaylen Brown, and Lillard operating within the same offensive system.
In short, adding Lillard's shot creation and clutch gene would have essentially ended competitive balance in the Eastern Conference once healthy.
Obviously, the fit would have been devastating for Milwaukee's title aspirations. With Jrue Holiday, Boston's biggest weakness was inconsistent point guard play and late-game shot creation beyond their two stars. Lillard solves both problems instantly while providing the kind of playoff experience that transforms good teams into dynasties.
From Milwaukee's perspective, Lillard's choice creates multiple strategic advantages. For one thing, it removes a potential super team from their conference while keeping a proven playoff performer in the West where he can't directly impact their postseason path. It also maintains roster construction balance across the East's contending teams.
The ripple effects extend beyond Milwaukee, of course. The championship windows for teams like Atlanta, Orlando, and New York are still wide open. Even teams like Cleveland and Detroit maintain realistic playoff aspirations they might have otherwise lost with Lillard in Boston.
Lillard's choice prioritized emotional connection over championship probability, a decision that benefits every Eastern Conference contender not named Boston.
The Bucks are still searching for their replacement, but Lillard's decision to chase Portland nostalgia over Boston championship certainty might have saved Milwaukee's title hopes without them ever knowing they were in danger.
Dame Time's final act as a Milwaukee Buck was protecting the very teams he used to compete against. And that's just as clutch as any late-game basket he hit for Milwaukee.