Why the Celtics should pursue Jrue Holiday from Portland


We are now living in the aftermath of one of the biggest trades in recent NBA history. Or of the last few months. It’s tough to tell, as player movement in the NBA has been bananas the past few years.

Damian Lillard was traded not to the Miami Heat as long expected, but rather to the Milwaukee Bucks, in a deal that saw major three-team movement, including Bucks shooting guard Jrue Holiday being sent to the Portland Trail Blazers. Holiday figures to only be with the Blazers temporarily as they’re committed to their youth movement, thus a subsequent trade or buyout figures to be next. Holiday will likely want to find his way back to a contender. Several teams are expected to be in the mix for Holiday’s services, a guard who plays plus-level defense (he had a rating of 112.4 last season), has postseason and championship-caliber experience and isn’t afraid to take a big shot.

The Boston Celtics should be one of those teams.

Yes, the Celtics have already been active this offseason in the trade market, sending veteran leader and fan favorite guard Marcus Smart away essentially for C/F Kristaps Porzingis. Plus, Grant Williams was salary dumped to the Dallas Mavericks as the C’s locked up forward Jaylen Brown to a $304 million supermax extension.

Just because the offseason has been very active doesn’t mean Brad Stevens’ work is done, especially with a rival and perennial NBA Finals favorite in the Milwaukee Bucks acquiring a superstar like Damian Lillard to add to Giannis Antetokounmpo and Kris Middleton.

A trade for Holiday would have to begin with guard Malcolm Brogdon, whom the Celtics already showed a willingness to deal away as he was the original centerpiece of a Porzingis trade before the then-trade partner Los Angeles Clippers passed due to Brogdon’s medicals.

However, Holiday and Brogdon’s salaries don’t match up, so the Celtics would have to get creative. A salary like Al Horford’s might be desirable, but Horford wouldn’t figure to be a part of Portland’s rotation, not to mention the Celtics have plans for him and it would leave them a big short. Relying on Porzingis and Rob Williams to be healthy enough all season to play center would be a dangerous, if not a foolhardy game.

Perhaps the Blazers would consider a buyout, but then they’re getting less in return for parting ways with their best player in franchise history. A trade is likely. We should hear about one and many interested parties very soon.

Brad Stevens has shown a ruthless knack for going after and getting done what he thinks is for the best with the Celtics. Acquiring Holiday, who has defended Brown and Jayson Tatum well over the years, would give them a dynamite starting five to match up with Milwaukee or any other team in either conference (lest we forget the Phoenix Suns also loaded up this offseason). Plus, a Holiday deal would allow Derrick White to be the centerpiece coming off the bench and be the super sub he was in 2022-23 for any number of injured players in the starting rotation, a role he excelled in.

A deal like this would take some critical thinking, bold movement, and creative dealings by Stevens and company, but when a rival makes a big move like Milwaukee did on Wednesday, answering back with a bold move may be the best course for a Celtics team trying to capitalize on the prime of their two superstar’s career. They went hard for the guy in Porzingis. Why not one more big move that could land Holiday and maybe raise a banner?

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