When Damian Lillard tore his Achilles tendon earlier this year, his career was in a precarious spot. It was reasonable for us to predict that his era in Milwaukee was coming to an end after just two years. The Bucks, as we know, would’ve had no use for Lillard after he spent the 2025-26 season in rehabilitation. On the other hand, if the Bucks decided to trade him before his contract expired in 2027, there might’ve been no predicting where the point guard would’ve landed up.

However, just months later, when the Milwaukee Bucks waived him, it gave Dame a chance to pick where he wanted to go next. As a free agent for the first time in his career, the nine-time All-Star had the opportunity to explore all the options. He could’ve gone anywhere with teams swarming up like bees to sign the veteran point guard. So, where did he go? Damian Lillard chose to go back to his home. He 34-year-old signed with the Portland Trail Blazers, where everything started for him.

Lillard signed a three-year $42 million deal with the Trail Blazers. However, that shouldn’t make you believe that he didn’t have options. On the contrary, he had plenty, according to ESPN’s Sham Charania. “Over a dozen teams made minimum and MLE offers to Dame. Two teams in particular, I’m told, that Lillard really considered: the Celtics and the Timberwolves. He held calls with both teams at different points.” Charania reported. The ESPN Insider revealed that Dame received several offers, but he only considered two of them.

The Minnesota Timberwolves and the Boston Celtics were the teams Lillard considered and not the Golden State Warriors. While we’ve all known the former Bucks star was in talks with the Celtics, given his close relationship with Jayson Tatum, the Timberwolves were a surprising one. Although one could argue that being a part of either of those two teams would’ve helped Dame achieve the one thing that has eluded him: A championship.

However, it seems that being in Portland with his three kids and his family meant a lot more to Damian Lillard than a potential shot at the title. For those of you who are unaware, last year Lillard went through a messy divorce with his ex-wife, and he’s been wanting to live in Portland closer to his family and kids. In fact, he even asked the Bucks management to let him continue his rehab in Portland, which they allegedly did not like. However, that is just the tip of the iceberg, apparently.

“He was not happy in Milwaukee”: Insider reveals the true reason behind Dame’s move to Portland

Remember Damian Lillard in the Portland Trail Blazers? He was the heart and soul of that Portland team. Many thought that this would be carried to Milwaukee when he got traded to the Milwaukee Bucks. But they were wrong. Although injuries played a major role in that, however, he never really looked comfortable in Milwaukee. This is exactly what Aaron Fentress of The Oregonian also thinks. “Also, he was not happy in Milwaukee,” Fentress reported on Thursday.

“He didn’t want to go there in the first place; he wanted to go to Miami. He relented and went to Milwaukee because his agent talked him into it, right? It gave him a chance to win. He wasn’t necessarily happy; there wasn’t anything against Milwaukee or the Bucks or anything like that, where he didn’t necessarily want to be there, he did want to win. But the fit never really worked out.” He added. Well, it’s no secret that what the Bucks thought was the recipe for success turned out to be one for disaster.

Fentress revealed how, despite wanting to head to Miami, Lillard was persuaded by his agents to sign for the Milwaukee Bucks. This indicates that he never really wanted to be in Milwaukee, and that doesn’t mean he hates the franchise or the place, but instead, he never planned for himself to be there. This made things difficult for him, and then soon he realized that it wasn’t going to work out. Nonetheless, all of that is behind Damian Lillard now, as he hopes to achieve new heights in his second stint with the Portland Trail Blazers.