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Damian Lillard looking like his old self brings up painful Celtics what-if

Lillard looked like his old self in Portland's first preseason game, which makes it painful for the Celtics to see in real time.
ByMatt John
Oct 7, 2026; Portland, Oregon, USA;  Portland Trail Blazers guard Damian Lillard (0) enters the line up to play against the Golden State Warriors at Moda Center.  Mandatory Credit: Jaime Valdez-Imagn Images
Oct 7, 2026; Portland, Oregon, USA; Portland Trail Blazers guard Damian Lillard (0) enters the line up to play against the Golden State Warriors at Moda Center. Mandatory Credit: Jaime Valdez-Imagn Images | IMAGN IMAGES via Reuters Connect

When Jayson Tatum looked mostly like himself upon returning to the Boston Celtics last season, it was a sigh of relief and a beacon of hope that Achilles tears aren't the death sentence they used to be. Damian Lillard pretty much did the same thing in his first preseason game with the Portland Trail Blazers.

In 19 minutes of a preseason exhibition, Lillard put up 15 points in 19 minutes, putting up a statline of five-for-11, including three threes. In a limited amount of time, Lillard gave fans good reason to believe Dame Time was still alive and well, but also gave the Celtics a reminder of what could have been.

When Lillard was waived and stretched by the Bucks, plenty of teams came a calling. Even if Lillard was coming off an Achilles tear and in his mid-30s, he's still Dame, and he could have been had for a discount with what Milwaukee was paying him in dead money.

Not only was Boston in on it, but they were among the finalists in the Dame sweepstakes before he opted to return to Portland. The Trail Blazers not just because of their history, but because it allowed him to be closer to his children.

You can't argue with that logic, but you can wonder what could have been if Lillard had been put on this Celtics team.

Lillard would have fit Mazzulla Ball amazingly

Okay, in case anyone doesn't know by now, Mazzulla Ball isn't just about three-pointers, but also about taking care of the ball, forcing turnovers, and offensive rebounds (creating as many possessions as possible).

Lillard would have been a perfect fit for two of those aspects: he's one of the NBA's best shooters and he takes care of the ball. Plus, playing next to Jayson Tatum would have not only given him room to operate, but it could have been a seamless partnership for both of them.

It's true that Dame did not fit well next to Giannis Antetokounmpo, but that may be attributed to the fact that the Greek Freak clogged his space. Tatum is a three-level scorer teams are actively afraid no matter where he is, which would have worked wonders for Dame.

In summation, Lillard would have been a better version of Anfernee Simons in Boston, and maybe that's even underselling it. For all the doubts about Boston this season, Lillard would have probably answered quite a few of them with the gravity he has.

It's very possible Lillard could find his way to the Celtics eventually - the Trail Blazers are one of the NBA's most oddly constructed teams - but whether he does or doesn't, it's hard not think about what could have been.

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