It's been almost one year since Damian Lillard's trade request out of Portland resulted in a blockbuster three-team trade that unexpectedly sent him to the Milwaukee Bucks. But it feels much longer than that for Blazers fans after the 21-61 season they endured. The good news is that a Rip City reunion isn't off the table for Lillard, who is arguably the franchise's best player in history. He previously has said, "I see there being a time where I play for the Trail Blazers," per Aaron Fentress of The Oregonian.
1. Bucks' all-or-nothing playoff scenarios
There are two scenarios where Lillard likely feels more inclined to move on from his situation with the Bucks and superstar Giannis Antetokounmpo. One is they continue to fall short in the playoffs. Despite entering last season with championship aspirations, the Bucks were upset in the first round by the six-seeded Indiana Pacers, losing in six games.
However, Lillard was limited to four games, and Giannis missed the entire series due to injuries. They could also chalk that season up to Lillard's acclimation to a new system and environment, as he had a relatively down year by his standards. But if Milwaukee continues to get bounced early in the playoffs, Lillard could reevaluate his landing spot. That's much more likely now that teams like the 76ers and Knicks have also significantly bolstered their roster; the Bucks might be the fourth-best team in the East.
The other timeline that could lead Lillard back to Portland is if the Bucks win the championship. It's a less likely outcome, but it's still feasible with two superstars on their roster. If that's the case, Lillard could be content achieving what he set out to do when he initially requested the trade, making him more open to returning to Portland.