5 teams who will regret not beating Bucks' offer for Damian Lillard

3. Why the Celtics will regret not trading for Damian Lillard

The Boston Celtics pretty much sealed themselves out of the Damian Lillard hunt when Jaylen Brown signed his historic five-year, $303.7 million extension. That made Brown trade ineligible for a year, but it also made him significantly less appealing. Portland would have ultimately had to bite the bullet on the same deal, but it's like a new car. Once you drive it off the lot, it loses its luster.

Still, Boston would have been wise to strike while the proverbial iron was hot. Lillard is roughly seven years older than Brown and there's value in continuity. Say what you will about the Celtics' locker room last season, but Brown has been through hellfire with Jayson Tatum. That group has gone to battle time and time again. There's a certain level of unshakable trust and camaraderie that comes with that.

Here's the plain and simple truth, though: Damian Lillard is significantly better than Jaylen Brown. That's true in a vacuum, and it's especially true for the Celtics. Boston's core weakness was a lack of reliable playmaking in the backcourt. Lillard can generate advantages and share the ball. Brown is a talented shot-maker, but he's a butterfingered ball-handler with little peripheral vision on drives to the cup. The fit with Tatum has always been strained; not because of the skills they share, but because of the skills they lack (Brown far more severely than Tatum, to be clear).

Lillard's ability to create from scratch, spread the wealth, and execute in clutch time — or should we say 'Dame Time' — would have set the Celtics apart from a crowded Eastern Conference. Instead, the Bucks are a head above now. Boston should have been making every effort to get Dame in-house, even after Brown's extension. That made it complicated, but not impossible. And the Celtics can't let complicated get in the way of them and Banner No. 18 right now.