Jrue Holiday Trade Grades: Celtics Take Big Swing With All-In Move

Boston makes a huge upgrade at point guard to go toe-to-toe with the Bucks as East favorites.

Jrue Holiday is headed back east.

The Celtics acquired the two-time All-Star guard in a deal with the Trail Blazers on Sunday, sending Malcolm Brogdon, Robert Williams, and two-first round picks to Portland. Holiday was traded to the Blazers as part of the Damian Lillard trade, and now he’s headed to one of his former team’s biggest rivals. Portland will acquire a 2024 first rounder from the Warriors as part of the deal, as well as a 2029 first from Boston.

Let’s grade the deal for both sides.

Celtics: B+

I am fascinated by this trade for Boston. After trading away Marcus Smart in June, the Celts are acquiring a clear upgrade in Holiday in this move. This is a huge bet on the center duo of Al Horford and Kristaps Porzingis, however. Boston has a fantastic top six in Holiday, Derrick White, Jaylen Brown, Jayson Tatum, Porzingis and Horford. Mixing and matching that group should allow for some pretty potent lineups offensively. But the depth after that is non-existent. Porzingis is injury prone and has played in 10 playoff games in his entire life. Horford is 37 and coming off the worst postseason of his career. Holiday makes a ton of sense in the wake of trading Smart, but dealing away Williams after also losing Grant Williams in free agency is a bold strategy.

Ultimately, the Celtics responding to the Lillard acquisition is the right move, and this sets up a juicy possibility for a conference finals matchup between Boston and Milwaukee. The resulting lack of depth for the Celtics cools me on the Holiday trade the slightest bit, but with how uninspiring the rest of the East is, it may not matter for Boston.

Holiday made his second All-Star team last season after averaging 19.3 points per game :: Trevor Ruszkowski/USA TODAY Sports

Blazers: A-

So the final haul for the Lillard trade for Portland is Robert Williams, Malcolm Brogdon, the 2024 Warriors first, the 2029 Celtics first, a 2029 Bucks first, and two pick swaps in ‘28 and ‘30 with Milwaukee. (The Deandre Ayton trade, though folded in with the Lillard deal, was almost certainly happening no matter where Lillard was sent.) This is pretty good! Joe Cronin deserves credit for his patience and creating a market for Dame when for months it seemed as though Miami was the only game in town. And I still think there is more room for the Blazers to wheel and deal here. Does Portland really need both Ayton and Williams? And Brogdon, despite his injury situation, will still likely be coveted by a handful of contenders. I do think the picks being returned here are a little underwhelming. Golden State will be good, and I don’t see the Celts falling off with Tatum and Brown by the end of the decade. But that’s nitpicking. Teams are never getting great picks in this scenario. The drama is over, the Blazers still have moves on the board and the organization is clearly feeling a sense of pride over not succumbing to Miami early in the summer.

Heat: L

As in, hold this, because the whammies keep coming for Miami. First the Heat lose out on Dame while the Bucks get better. Now the Celtics make a major improvement as well. Both teams the Heat beat en route to the Finals have taken major swings. Meanwhile, Miami has lost two starters from last year’s squad and is in a bit of a no-man’s land as Jimmy Butler enters his mid-30s. You can’t count out Butler, Bam Adebayo and Erik Spoelstra entirely. But this has been a disastrous week for the franchise.