THOUGHTS | DAMIAN LILLARD GETS WAIVED

Okay, ESPN got me thinking. Damian Lillard is now walking a path that's starting to look a lot like the ones Russell Westbrook, Bradley Beal, and in some ways, even De’Aaron Fox have taken.

Remember, Westbrook was just 30 years old when he was pushed out of Oklahoma City in a trade that sent him to Houston. WB wasn’t declining yet, but the Thunder wanted to reset. Since then, he’s been on five teams in six seasons, and his reputation has taken a hit. Beal, on the other hand, waived his no-trade clause and landed in Phoenix, only to become the fall guy when things went south. As for Fox, it’s tough to imagine him feeling completely secure in San Antonio now that they have Stephon Castle and Dylan Harper threatening his spot in their young core with Victor Wembanyama. Even Myles Turner could have stayed in Indiana and further build a legacy, but now he’s also in a position where he needs to prove himself all over again with a hefty price tag.

Here’s the thing. When you stay loyal to a city, it often feels like the city will never turn on you. But once you leave, especially after spending most of your career somewhere else, your new team’s fanbase won’t always understand what you’ve been through.

They won’t connect with your personal journey.

They just want results.

Lillard gave everything to Portland. It’s hard to imagine the Trail Blazers doing him dirty. But Milwaukee? This isn’t about loyalty. It’s about making sure Giannis Antetokounmpo stays happy. And it’s kind of wild when you realize that Dame got injured while hustling for the Bucks. He tore his Achilles chasing a rebound, trying to help the team and the city.

That says a lot about his character.

Still, this is how the league works now. Ever since the Bucks won their title in 2021, they’ve done everything they can to keep Giannis content. That’s why they traded Jrue Holiday for Dame. That’s why they picked up Kyle Kuzma, since Khris Middleton hasn’t looked like his old self. And they let Brook Lopez walk, because he’s clearly on the decline.

Now the Bucks are looking at a payroll that could hit close to $50 million per year in the next few seasons because of the contracts of Lillard and Turner. Dame will be free to sign with any team, likely near the end of the regular season. He might join a contender and try to help out for a playoff run. He might even return to Milwaukee, as part of an insane scheme to turn chicken shit into chicken gold. That could be exactly what Giannis wants to hear.

But here’s the tricky part. If Lillard joins a playoff-bound team, he runs the risk of being remembered like Mitch Richmond with the 2002 Lakers or Tracy McGrady with the 2013 Spurs. Both were legends who tried to chase rings, barely played in the Finals, and weren’t brought back the next season.

Both retired quietly.

Dame is 34, the same age T-Mac was in that Spurs stint, but he’s healthier and still capable of helping teams, whether as a starter or a bench piece. Still, the days of being a franchise player are likely behind him. He’s now a hired gun. And in today’s NBA, that role comes with plenty of uncertainty.

Organizations are in the same boat. Take Dallas as an example. They’re stacked with talent right now, but one playoff collapse could cause the whole roster to blow up. That’s how fragile success is in this league.

So for Dame, this next move has to be the right one. And for the Bucks, they need to be absolutely sure that Myles Turner is worth the investment. Because whether you're a star or a franchise, one wrong step can cost everything.