NBA Rumors: Damian Lillard Trade to Bucks Was 'Surprise' to Execs Around League

The Milwaukee Bucks' acquisition of Damian Lillard from the Portland Trail Blazers on Wednesday shocked more than just basketball fans.

According to Jake Fischer of Yahoo Sports, the deal "took rival personnel largely by surprise."

Fischer wrote:

"Most of the chatter surrounding Lillard's future over the last week, as the Blazers increased conversations regarding their All-NBA guard, was centered on Toronto's legitimate interest and approach for Lillard, sources said, in contrast to Portland's nonexistent negotiations with Miami. The Bucks quietly sought Lillard in the background of those theatrics, doubling down on the very script Milwaukee followed to satisfy [Giannis] Antetokounmpo before the 2020-21 campaign, when they acquired Holiday from New Orleans."

Lillard generated plenty of interest around the NBA after requesting a trade from the Trail Blazers earlier this offseason.

The Miami Heat were Lillard's preferred destination but the franchise wasn't "offering even close" to their full tradable assets in a potential deal for the veteran point guard, according to Barry Jackson of the Miami Herald.

The Toronto Raptors had also been heavily linked to Lillard in recent weeks as talks with Miami seemingly went nowhere. According to Andscape's Marc J. Spears, the Raptors were a "real contender" to land the seven-time All-Star.

The Trail Blazers "have long coveted" Raptors star OG Anunoby" Ryan Wolstat reported Tuesday, but he added Wednesday that Toronto "simply would not dangle" him in a deal for Lillard.

With the Raptors unwilling to include Anunoby in a potential deal, it's possible that's when the Bucks swooped in with an offer that Portland couldn't refuse.

Lillard's agent, Aaron Goodwin, informed the Bucks 10 days ago that he would be interested in a move to Milwaukee, according to Spears. He's now teaming up with Giannis Antetokounmpo in pursuit of winning a championship.

After Antetokounmpo cast doubt on his future in Milwaukee on multiple occaisions this offseason, it theoretically shouldn't have been much of a surprise that the franchise took a big swing for Lillard.

Antetokounmpo is under contract through the 2024-25 season with a player option for 2025-26 that he can decline to become a free agent. The more the Bucks win, the larger the chance they have to retain the two-time MVP for the long haul.