If NBA offseason storylines were mixtapes, Damian Lillard would be the lead single—remixed, remastered, and still spinning on every contender’s playlist. Just when you thought his plotlines couldn’t get wilder, along comes a triple scoop of Portland goodwill, Boston courtship, and Milwaukee chaos that has fans wondering if the league’s new motto is “Plotting With the Punches.”

Let’s break it down before another unexpected Woj bomb drops. First up—Portland. Remember when Damian Lillard got traded and the Blazers shipped out Jrue Holiday faster than a bad trade machine idea? Well, reevaluate because Jrue is back in Rip City. But here’s the twist: Dame might’ve given the deal a friendly nudge.

As insider Jake Fischer spilled, “I know Dame reached out to Jrue and kind of like talked well about Portland as a franchise and a city.” That’s right—Damian Lillard, in classic “good guy of the NBA” fashion, vouched for Portland even after the dramatic exit. Imagine getting traded and still selling the timeshare to the next guy. That’s some next-level professionalism… or Stockholm Syndrome.

Portland isn’t playing it safe either. With Jrue back, they’re going playoff hunting like it’s Black Friday at Best Buy. As Fischer added, “I think he’s happy to be there too.” Considering how Jrue just helped Boston bag a championship, that’s a massive vote of confidence for a young Blazers squad hoping his defense holds up better than their playoff hopes usually do.

Next, let’s shift our attention to the Celtics, who are going through a rebuild…and then some this off-season.

Boston’s Master Plan: Rehab, Recruit, Repeat

On to Boston, where Damian Lillard might be getting the full New England courtship package. You know—chowder, duck boats, and Jayson Tatum sliding into your texts. According to Gary Washburn, “I just was told that they’re communicating and Tatum is recruiting. Tatum is the face of the franchise.” The Celtics aren’t waiting for Dame Time; they’re setting the clock early. Washburn even joked he didn’t know “if they’re like FaceTiming every day… but they are communicating.” NBA recruitment: because nothing says bonding like Achilles rehab group chats.

Let’s be clear, though—the Celtics aren’t exactly flush with cash. The best they can offer Damian Lillard is a vet minimum or a $5.7M exception. But if Dame’s embracing “Forever Evolving and Rolling with the Punches! They can’t FW me! Cheers to 35!” (his actual birthday caption), money might not be the dealbreaker. Especially if the Celtics offer a chance to heal up alongside Tatum in a no-pressure comeback season before a real title shot in 2027.

Meanwhile, Milwaukee pulled the financial equivalent of a Hail Mary flea-flicker with their decision to waive Damian Lillard and stretch $112.6 million of his contract over five years. That’s over $22M in dead money per year. Because who needs a salary cap when you’ve got Giannis to keep happy?

Coach Doc Rivers admitted it wasn’t exactly a cakewalk: “Stretching Dame’s contract, which was not easy to do… gave us more flexibility and we can sign more guys.” Translation: they swapped a future Hall of Famer for a shot at keeping Giannis and added Myles Turner for good measure.

The front office scrambled harder than a playoff rotation trying to explain this to the fanbase. Rivers again: “Giannis came to me the day after the season and we were talking about next season already.” And Bucks President Peter Feigin tried the ol’ “nothing to see here” routine: “We kind of laugh internally… Giannis loves Milwaukee, Milwaukee loves Giannis. We’re in a good place.”

Well, if “a good place” includes carrying Dame’s contract like an unwanted subscription fee, sure. In summary, Damian Lillard’s the playing mentor for Jrue’s Portland homecoming?  Is Jayson Tatum actively pitching Boston like a door-to-door salesman?  Milwaukee’s financial gymnastics stunt left everyone dizzy.

Dame’s also leaving cryptic IG captions like “To Be Continued,” fueling more rumors than a trade deadline Reddit thread. If he does land in Boston, it’ll be the ultimate buddy-rehab comedy: two Achilles injuries, one title chase, and zero pressure. If he sticks around Portland’s narrative, it’ll be the feel-good loyalty story we didn’t see coming. And if Milwaukee’s gamble fails… well, at least they’ve got Cole Anthony.

The offseason soap opera starring Damian Lillard keeps rolling—and whether it’s recruiting, recovering, or rewriting legacies, one thing’s for sure: this is one storyline worth setting your league pass reminders for.