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Damian Lillard traded to Bucks – Big questions after the most shocking deal of the NBA offseason

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Who saw that trade coming? Our NBA Insiders are breaking down the blockbuster deal that revamps a juggernaut in Milwaukee.
Wow … what?
After nearly an entire NBA offseason of stasis between the Portland Trail Blazers and Miami Heat, superstar point guard Damian Lillard has been traded to the … Milwaukee Bucks!?
The shocking move — a three-team deal that also sent guard Jrue Holiday and 2018 No. 1 pick Deandre Ayton to the Trail Blazers and big man Jusuf Nurkic to the Phoenix Suns — doesn’t just dash the hopes of Heat fans, it creates an even more powerful juggernaut in Milwaukee led by two-time MVP Giannis Antetokounmpo, who now has another All-NBA talent by his side.
Did Milwaukee just become the unquestioned 2023-24 NBA title favorite? Which teams should be calling Portland about a deal for Holiday? Did Phoenix get better around its three stars? Where does Miami go from here?
Our panel of NBA insiders is breaking down what the biggest trade of the offseason means for all sides.
Jamal Collier: League-altering. This move elevates the Bucks into superteam status, changes the conversation around Antetokounmpo’s impending future and sets the table for Lillard, after a decade in the league, to shine on his first true playoff stage with championship expectations.
Bobby Marks: Not risky. On the surface, trading for 33-year-old Lillard and the $200 million left on his contract is a huge gamble, especially considering Lillard has played a total of 87 games in the past two seasons. But when you factor in that the cost to retain Holiday could have reached $223 million on a new contract, the risk is mitigated. Also, if Holiday left next offseason as a free agent, Milwaukee had only the $12.9 million non-taxpayer midlevel exception to replace him.
Tim Bontemps: Stunning. I’m not sure it makes the Bucks much better, but it continues a trend of doing things that (seemingly) are designed to make Antetokounmpo happy. And if this helps him stay in Milwaukee long term, it’s an unquestionable win.
Dave McMenamin: Clyde Drexler-esque. After 10-plus years as the Blazers‘ No. 1 option without reaching the championship mountaintop, Drexler was traded to Houston in 1995 to team up with the game’s most impactful big man in Hakeem Olajuwon to help Houston win a second ring (and his first). Nearly three decades later, Lillard could follow the same script with Antetokounmpo in Milwaukee.
André Snellings: An absolute game-changer. The Bucks have been my preseason favorites to win the championship in each of the past three seasons, but after winning in 2021 they have been really impacted by the injuries to All-Star second option Khris Middleton. Giannis is the most dominant player in the NBA and their team defense is tough, but they lacked the volume shooting from distance to be able to properly maximize their potential. Lillard gives them the best shooting-scoring option on the perimeter east of Stephen Curry — and on paper makes their team appear to be unstoppable in the East.
Richard Jefferson says the Bucks have become his ‚“way-too-early favorite“ with the addition of Damian Lillard.
Collier: Powerful. His words carry weight. After Antetokounmpo cast doubt on whether he will stay with the franchise long term, the organization responded by pairing him with the best player he has ever called a teammate.
Bontemps: Satisfied. Giannis has talked openly about wanting to see the Bucks fully committed long term. This trade costs the Bucks a key option in Holiday and a ton of tax dollars. Now, let’s see whether Antetokounmpo can lead the Bucks back to the promised land.
Snellings: Elated, like he just got another 50-piece Chick-n-Mini meal after winning Finals MVP. Giannis has been holding the Bucks‘ feet to the fire to make championship moves, and this is about the biggest move possible. Add in Lillard’s ultracompetitive „Dame Time“ attitude on top of the incredible talent fit and it’s hard to imagine what else Giannis might be looking for before committing to an extension. The Bucks have shown they are all-in on helping him win more chips in Milwaukee.

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