Grade the Trade: Celtics land Lillard but keep Jaylen in new proposal

Do the Celtics say yes to this trade?

The Celtics struggled against both the Philadelphia 76ers and Miami Heat last season for two primary reasons: their shooting ran hot-and-cold, and against the very best defenses their shaky ball-handling slowed down their half-court penetration and caused costly turnovers.

Trading Marcus Smart for Kristaps Porzingis didn’t solve either issue, but trading for Damian Lillard would instantly solve both. He is one of the league’s best ball-handlers and a master of the pick-and-roll, with his threat of pulling up opening up space to drive into the defense or for his rolling partner to have a 4-on-3 advantage. That’s an action the Celtics couldn’t run at a high-level last season.

Lillard’s shooting would give the league’s most willing 3-point shooters one of the best 3-point weapons in the entire league. He can pull up from anywhere, he moves off-ball, and his relocation game will play well to the Celtics’ strength on the offensive glass. His defense is below average, but the Celtics will essentially play all good defenders around him in the rotation, and his offense more than makes up for it.

The cost to add Lillard would be exorbitant. The Celtics send out nearly all of their future draft capital and do so in order to pay three players nearly all of the salary cap for the next few seasons. They will live over the second apron and be limited to just minimum contracts to maintain their roster.

But the upside? The upside is that a team with Lillard, Brown, Tatum, and Porzingis, with Al Horford and Derrick White as glue guys, can absolutely win a title. The Celtics should be trying to win a title right now, and trading for Lillard is a great way to pursue that goal. It’s expensive, and it’s unlikely (nearly impossible salary-wise) but it’s one more big swing for a team that loves to make them.

Grade: A