The Eastern Conference Arms Race, Part 2: Boston Celtics
• Celtics acquire Holiday
• Blazers acquire Malcolm Brogdon, Robert Williams III, Payton Pritchard, two first-round picks
The case for the Celtics: Boston has a two-year window it must maximize before
Jayson Tatum’s next contract kicks in and the money owed to he and
Jaylen Brown becomes a real burden. The Celtics should be going all-in to acquire players who can help them now. Holiday replaces what
Marcus Smart brought to the team defensively while also adding more consistent offensive play. The Celtics could close with a foursome of
Derrick White, Holiday, Tatum and Brown, a perimeter group that can defend at an exceedingly high level plus create quality shots offensively. Holiday would also be an awesome fit next to
Kristaps Porziņģis in drop-coverage scenarios.
To make the trade math work, the Celtics have to include Brogdon and one of
Al Horford or Williams. I opted for Williams because Horford has proven to be more reliable at this stage due to superior health and a more well-rounded offensive game. Williams’ defensive upside is vast, but I don’t love the idea of playing him with Porziņģis, whereas I can envision Horford doing so occasionally. The Celtics would need to make an additional preseason trade to add further frontcourt depth. Maybe they could rope in Oklahoma City as a third team to get one of their surplus youngsters like
Jeremiah Robinson-Earl, in exchange for one or two second-rounders.
Acquiring Holiday gives Boston the offensive floor spacing and rim protection it seemed to want from Porziņģis in addition to the perimeter defense of the departed Smart. Remember: The original Porziņģis deal reportedly included Brogdon over Smart, so combining shooting and defense was obviously on Boston’s mind from the get-go.
Does this work for Portland? I think the Blazers will likely get a better offer than this. The Celtics could provide Portland draft picks that are closer to conveying — they own all of their own selections, plus a 2024
Golden State first-rounder — but those picks would not have nearly the same upside as ones from the Clippers or 76ers at the end of the decade. The Celtics are going to be good for a while due to the ages of their core players. Pritchard would be a nice get as a backup point guard, and he’d be an immediate fan favorite as a Portland-area kid. The Blazers might be able to flip Williams and Brogdon later in the season for additional draft capital, but I don’t think either would return much more than late first-rounders, if that, due to their injury histories.