It's no secret that the offseason situation revolving around former Portland Trail Blazers star Damian Lillard and general manager Joe Cronin was a tumultuous rollercoaster. In an interview with Sam Amick of The Athletic, Lillard reinforced the frustrations he felt during the trade process where his request was to initially go to the Miami Heat.

Lillard said in the interview with The Athletic that it was “irritating” knowing that he was most likely not getting what he wanted from Cronin and the Trail Blazers organization.

“It was anything to go against what I would have wanted,” Lillard said. “That part was irritating. Just based off how it was happening, I knew (it wouldn’t be Miami).”

It came to a point where Lillard didn't see himself ending up in a Heat uniform to start the upcoming season as he heard that there were a lot of teams mentioned.

“(The Blazers) hadn’t talked to Miami. So once it started happening like that, then I started hearing about all these other random teams, I was like, ‘I’m probably not going to Miami.’ So I wasn’t holding on to that too (much).”

At the end of the day, Lillard wanted to go to a team that had a winning mentality and while the Heat definitely fit the bill, the Milwaukee Bucks do so as well. Pairing up Lillard with Giannis Antetokounmpo and the rest of the roster could prove wonders for the Bucks. With the news of the trade, the Bucks have become a popular pick to possibly win the East and reach the NBA Finals once again like they did in 2021.

Lillard last season averaged 32.2 points, 7.3 assists, and 4.8 rebounds per game as he's now going into his 12th season in the NBA, his first not being a Trail Blazer. The Blazers start their season Wednesday against the Los Angeles Clippers while the Bucks begin on Thursday vs. the Philadelphia 76ers.