Colin Cowherd Floats Damian Lillard-Celtics Trade Blazers Should Accept

Damian Lillard remains the subject of trade rumors, and the Boston Celtics keep coming up when discussing possible landing spots for the Portland Trail Blazers superstar.

FS1’s Colin Cowherd on Monday explored various hypothetical trade packages — from Portland’s perspective — to determine whether he’d rather keep Lillard or swing a blockbuster deal.

In most cases, Cowherd would prefer to stick with Lillard, a six-time All-Star with a reputation for being one of the NBA’s top scorers and a clutch performer in crunch time. The Celtics, however, have the pieces to put together a trade offer Cowherd believes the Blazers should accept, if given the opportunity.

Here’s the theoretical trade floated on “The Herd with Colin Cowherd” that would send Lillard to Boston:

Blazers receive: Jaylen Brown, Marcus Smart and multiple first-round picks.

Celtics receive: Damian Lillard.

Now, here’s Cowherd’s explanation for why he’d pull the trigger if he were the Blazers:

“This is one of the rare, where if I’m Portland and I know the goal is to win a championship, I would take the Celtics’ offer. Jaylen Brown is only 24. He has gotten better every year. He just averaged 25 (points per game). Marcus Smart’s only 27. Tremendous defensive player. His offense is spotty. But the Celtics have first-round picks in ’22, ’23, ’24 and ’25. If I can get two of those, Jaylen (and) Marcus Smart, I can start to solve some of my issues and I would be a much better defensive team without having to give up all the offense. That move I would make.”

Bleacher Report’s Andy Bailey on Monday proposed the exact same trade, adding a 2023 first-round pick and a 2025 first-round pick to a Celtics package centered around Brown and Smart. And it’s an intriguing idea, if nothing else, as pairing Lillard with Jayson Tatum would give Boston an explosive 1-2 punch.

That said, Lillard is 6 years older than Brown and has a max contract extension in place that’s about to pay him a boatload of money through the 2024-25 season. The potential offensive boost Boston would receive by swapping Brown and Smart for Lillard might be offset, in the collective, by the defensive downgrade and the decreased lineup versatility.

The Celtics need to augment their roster, sure. But ultimately, breaking up the Tatum-Brown pairing might not be the best course of action, even if taking that bold step would put Lillard in Green.