Damian Lillard's move to Milwaukee is basically a way to promote growth. Yes, he's the most loyal player, but loyalty can also be a security blanket for a person.
Moreover, this is Portland pushing their stubborn superstar away because they want him to be happy.
I know Lillard has been entertaining offers for some time now but unlike most NBA superstars, there is a reluctance to his championship yearnings. Lillard is like the old 90s stars in the sense that the only way he could win a title is by joining a championship team way past his prime like what Mitch Richmond did with the Los Angeles Lakers during the Kobe/Shaq era or just accepting it, like the case of most players from that era - ranging from lifers like Reggie Miller and John Stockton, late-career switchers like Karl Malone and Chris Mullin, and even chasers like Charles Barkley, Grant Hill, and Dominique Wilkins.
Dame Time had expired in Portland ever since the failed experiment that sent CJ McCollum to the New Orleans Pelicans.
Is Lillard a good fit in Milwaukee?
I don't know about this. Giannis Antetokounmpo can hold a team on his own but this is only if the league isn't cluttered with superteams. I know Giannis won his title with Khris Middleton and Jrue Holiday. Technically, they are super trio. All of them are all stars and at least they are stars that at that point, rarely got injured or had rest days. Lillard is going to join a team with champions. I don't know if he can impose his will, but he was also given an insane distinction.
This is Dame's Top 75 recognition.
Honestly, I don't think he deserves this. At least, not yet. Lillard is a talent at the peak of his career and despite the All-NBA Teams, he has no championships. Dwight Howard should have been in his place, but because of recency bias, he was snubbed.
But I guess now, Lillard is right for the spot.
Also, it feels like Lillard is going to have the same career trajectory as former Portland top stud Clyde Drexler. Like McCollum, Drexler has his own backcourt sidekick in Terry Porter, and like what The Glide did in Houston, Lillard is going to be the semi-sidekick as if Giannis is his version of Hakeem Olajuwon.
Phoenix lost Deandre Ayton but gained a slew of enforcers. Portland gained a one-two punch in Holiday and Ayton. In all, I think Portland got the best of the deal because the Lillard trade also assured Giannis' stay in Cream City.
And I guess this is the main reason why the trade happened in the first place. Milwaukee gave away two important cogs in Holiday and Grayson Allen so they could have the ultimate backup for their Greek Freak. The fact that Giannis sacrificed a Greek national team spot means that the NBA wear-and-tear is taking its toll on him. I think Giannis is not the type to get pissed at the opportunities given to Lillard so these two could work just fine.
What that in mind, we know whose team this is.