If the Milwaukee Bucks are truly interested in salvaging their championship window with Giannis Antetokounmpo, they should trade Damian Lillard.
Ten games into the start of the 2024-25 NBA season, I'm not sure there's any scenario in which the Milwaukee Bucks could've gotten off to a worse start. The Bucks are 2-8, Khris Middleton has yet to make his regular-season debut as he continues to recover from offseason surgery, and the Giannis Antetokounmpo trade winds are beginning to blow. As the temperature begins to heat up for the organization, this front office could feel forced to make a potential championship-window-saving move before it all blows up in their face.
While it may not seem likely, the moment that Giannis demands a trade, it's over for the Bucks. The hope is that it never gets to that point. But the argument could be made that we're as closest as we've ever been to Giannis asking out from Milwaukee. As the front office explores smaller-level deals that could help dig the team out of this early-season hole, I can't help but wonder if there's another panic-button move that could be in play that no one seems to be talking about right now. Trading Damian Lillard.
The risk in extending Giannis Antetokounmpo's title window
If the Bucks are genuinely interested in salvaging the Giannis championship window, there's no question a bold move needs to be made. But I do imagine that the best chance the Bucks have at making a bold move involves trading Lillard, not Bobby Portis and Pat Connaughton. With all due respect to Portis and Connaughton, neither of those players is likely going to return a needle-moving addition.
With how the Bucks have performed in the Eastern Conference over the last few seasons, it's become pretty clear that major changes are needed. Interestingly enough, the front office hoped that the move for Lillard would be the big change that would help the Bucks reemerge as a championship favorite. At least through the first season-plus of the experiment, that didn't solve any issues the Bucks had. It may have only magnified them.
At this point, the evidence suggests that trading for Lillard may have been a massive mistake for the Bucks. If Milwaukee is desperate to salvage the build around Giannis, trading Lillard may be the next logical move. It's certainly a huge risk. Because if the Bucks trade Lillard and it fails, that probably points to the end of Giannis' time in Milwaukee. I can't imagine he'll want to wait around for another rebuild.
However, it may be a risk that the Bucks might need to take. If they continue to downward spiral into irrelevancy in the Eastern Conference, trading Lillard might be the only move that could extend Giannis' diminishing championship window in Milwaukee. It's certainly a huge risk but the Bucks are inching closer and closer to the point where they may not have any other options. It's finally time to begin discussing the real possibility of the Bucks trading Lillard. Not only to save the season but perhaps the franchise.