NBA expert considers the Milwaukee Bucks’ acquisition of Damian Lillard a defining moment of 2023

The trade for Lillard came out of nowhere.

Jonas Panerio | Jan 7, 2024

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Milwaukee Bucks

September is usually a dull time for NBA happenings. The free agent frenzy has died down, teams have had their rosters set for a while, and all eyes are on the upcoming season. But in 2023, one move caught the attention of fans and analysts alike – the Milwaukee Bucks’ acquisition of Damian Lillard.

Tense time

According to The Athletic’s Sam Amick, the move, which happened midday on September 27th, sent shockwaves across the league. One, because nobody saw it coming, and two, because of its impact on the entire league.

Three months before, Lillard had expressed his desire to be traded away from the only team he had played for in his NBA career, the Portland Trail Blazers. He added that his preferred team was the Miami Heat. However, Portland’s general manager, Joe Cronin, opposed sending Dame to the Heat, creating a stalemate that lasted a few months.

“The tension had risen on both sides, but there was no resolution in sight. So Lillard, no doubt concerned that he might get sent to a team that wasn’t of his liking, told the team that he’d be patient and professional for as long as it took to get a deal done that worked for both sides. In the end, there was no need for that sort of gesture: The blockbuster trade that sent him to Milwaukee to join forces with Giannis Antetokounmpo was about to happen,” Amick wrote.

"My agent called me he said '[Trail Blazers] traded you to [the Bucks]'... My first thought was like everything I was leaving behind... This is where I’m supposed to be right here. It’s time to win.”

—Damian Lillard

(via @Bucks) pic.twitter.com/veps9hdMKl
— ClutchPoints (@ClutchPoints) October 19, 2023

High shock factor

In the weeks following Lillard's trade request, the rumor mill was buzzing with potential destinations for the star point guard. However, no one could have predicted the massive move that would happen. Milwaukee’s front office kept its head down and worked in the shadows to finalize the shocking move, delivering a moment nobody would soon forget.

“In terms of shock factor, the deal that went down midday on Sept. 27 was extremely high because the Bucks had operated in the shadows the whole time,” Amick continued.

“I didn’t have any sense that the Bucks were willing to trade Jrue Holiday, which meant there was no reason to suspect Milwaukee as a major player in the Lillard sweepstakes. And I, like so many others, couldn’t have been more wrong.”