Portland sets the East on fire with the Jrue Holiday trade

Oh, Trail Blazers, you scamps! Positively scallywaggian!

Just days after sending All-NBA point guard Damian Lillard to the Milwaukee Bucks in exchange for another All-Star point guard, Jrue Holiday, Portland turned right around and sent Holiday to the Bucks’ biggest threats in the East, the Boston Celtics.

Here’s a live look at Portland GM Joe Cronin after setting the Eastern Conference on fire:

The Grinch GIFs | Tenor

(The best part: Cronin might not be done sowing chaos yet. Malcolm Brogdon, who was sent to Portland as part of the package for Jrue Holiday, is the reigning Sixth Man of the Year and another likely trade candidate. Perhaps Miami, whom Cronin may or may not despise, will settle for the third-best Blazer point guard to be traded this week?)

Milwaukee had to have seen a Holiday move to a contender coming (Boston and Miami were the two most logical suitors), but it still must sting. Their trade for Lillard somehow improved their team without creating more separation from Boston.

I’ve heard a surprising amount of “meh” and “well, actually…” and “but Rob Williams!” on the Internet. Put that silliness in a bottle and back in the cabinet to age for a more appropriate occasion; this trade was a big win for the guys in shamrock green.

Let’s start with what went out. Malcolm Brogdon, Robert Williams, Golden State’s 2024 first-rounder, unprotected 2029 Boston first-rounder. That’s a haul.

Brogdon was a deserving Sixth Man of the Year winner last year, but despite his marksmanship, Boston observers were often left a little cold by his defense and tunnel vision. An elbow injury in the playoffs not only limited his effectiveness but also forced his removal from the original Kristaps Porzingis trade. His inclusion in that aborted trade angered Brogdon, who asked out. He’s gotten his wish now.

The picks are significant. Golden State should be a good team next year, but in a crowded Western Conference, it only takes one poorly-timed injury to send any team into the lottery. The Celtics assuredly will look wildly different in 2029, and though superstar Jayson Tatum will still be in his prime, it’s impossible to project what any team will look like that far down the road.

Robert Williams is the painful inclusion. There have been stretches where he’s been one of the most impactful defenders in the league, but in his five-season career, Time Lord has averaged fewer than 42 games played — half a season. When he returned last year, he looked like a shell of himself, and there’s no way of knowing if he can reach 90% of what he once was. He might not even get a chance to show it.

Finally, the Holiday trade wasn’t made for just this year, which is a double-edged sword. The Celtics paid a pretty penny, and they’ll likely agree to an extension to keep Holiday in Boston for longer. Between Jaylen Brown’s new contract, Kristaps Porzingis’ extension, Tatum’s looming supermax, and Holiday… something will have to give soon.

But you know what? I like the move, anyway.

As much as I love Derrick White, point guard was the most obvious position of need for Boston after the Marcus Smart trade, particularly considering Brogdon’s unhappiness and the Bucks’ addition of Lillard. While White is a tremendous defender and improved offensive player, he’s not the kind of initiator who ideally would run an offensive system day-in and day-out. Holiday isn’t prime Chris Paul, but he’s better than White or even Smart in that regard.

For one, Holiday is a sniper (at least during the regular season) who has hit 39.5% of his triples over his three-year tenure in Milwaukee on solid volume. He can be a little sloppy with the ball and can take strange, early-shot-clock jumpers on occasion, but he’s a bullying driver and strong passer who averaged 7.4 assists last season. Thanks to his time with Giannis, he’s used to playing next to a ball-dominant forward, so he won’t have issues ceding control of the play to Tatum (or Brown, or Porzingis, or whomever) the way Smart sometimes did. His shooting stats may look even better this season thanks to the five-out offense Boston will run; no Giannis (and his accompanying defenders) to clog the lane here.

Defensively, of course, Holiday is one of the best point-of-attack defenders in the game, a master screen-avoider and handsy, physical deterrent. His presence will give the Celtics much more flexibility to play drop defense with Kristaps Porzingis at center (since drop defense relies upon guards fighting over picks to harass the ballhandlers and prevent easy pull-up threes), and he’s equally effective in switching schemes. Holiday single-handedly unlocks the defensive versatility I believed the Celtics had sent out the door in a poorly-packed suitcase with Grant Williams and Smart.

Holiday is often dinged up, but he typically plays through injuries (67 games in each of the last two seasons isn’t bad by today’s standards!). His postseason shooting woes have been well-documented here and elsewhere, but he should be more effective as his offensive burden is lessened. On many nights, he’ll be the fourth option, and I doubt there’s a better fourth scorer in the league. That reduces the pressure on him to perform and the impact if his playoff troubles do resurface — this team doesn’t need him on offense the same way the Bucks did.

Boston’s top six are incredible: Holiday, White, Brown, Tatum, Porzingis, and Al Horford. All are above-average defenders at worst, and none are a liability on offense. Moving Williams for Holiday creates more defensive flexibility: the Celtics can go with a one-through-five switching defense with Horford at center, a massive two-big lineup where White (or maybe even Brown) sits, or a Bucks-like drop coverage with Porzingis performing the role of Brook Lopez. Few teams can run so many defenses so well.

The Suns and Bucks arguably have more postseason offensive upside, but this sextet has historic two-way potential that could lead the regular season in offensive and defensive rating. As a six-man unit, I’m not sure they have any weaknesses. There’s still a lack of elite playmaking and passing, and they might be an average-ish rebounding team… but we are looking for nits with a microscope.

However, the trade certainly whittles down Boston’s depth even further. After those six, the Celtics will have question marks. But I’m optimistic that Boston’s depth won’t be an albatross. Payton Prichard? Luke Kornet? Sam Hauser? Casual fans will scoff, but all three players generally performed well when given the opportunity last season. These are serviceable, young-ish vets with defined NBA skills (shooting for Hauser and Pritchard, kontesting shots for Kornet). Boston’s top six is so deep and so good that there will always be at least three above-average players on the floor at any given time, so even if one of the reserves struggles, the roster should be resilient.

I also like offseason addition Oshae Brissett, a forward and break-in-case-of-emergency small-ball center, to add some ruggedness to the frontline. His outside shooting (a trait coveted by Boston) hasn’t always been there, and he fell out of the rotation on a mediocre Indiana Pacers squad last season, so perhaps my confidence is misplaced. But without Smart and Grant Williams, the Celtics needed a little more toughness, and Brissett fits the bill.

Perhaps draftee Jordan Walsh, whose defense stood out in Summer League, will be given a similar role on the perimeter. Neemias Queta is a massive throwback center on a recently signed two-way deal. He could be brought in full-time as big-body insurance. Lamar Stevens was signed as another defensive forward who could eat up some regular-season minutes. And if none of these players click? The Celtics still have plenty of draft assets available to trade (although matching the salaries for a non-star could be tricky, given how top-heavy Boston’s books are).

On Portland’s side, they received another nice haul, albeit one that surprised me a little. The Blazers apparently plan to keep and rehabilitate Robert Williams, a player I’ve always admired but whose health has made him untrustworthy. If he can tap into his talents again, though, he and Deandre Ayton give Portland a promising, young center duo who can also play with each other for stretches. His screening, passing, and vertical spacing should make the lives of Portland’s many young guards much easier.

Portland now has oodles of draft picks at the end of the decade, when their young players will be firmly in their prime (and newly expensive). Loading up with cheap rookies is a fantastic way to bolster a roster’s talent level when an org is capped out.

But in the short term, this is all about the Eastern Conference. The Bucks’ trade for Lillard upped the ante. Only Boston was willing to pony up and stay at the table.  

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Michael Shearer is an NBA obsessive who writes to answer the questions he has about the league. You can follow him @bballispoetry. He also is a contributing writer for Fansided at Hoops Habit and writes a free NBA analytical newsletter at basketballpoetry.com that goes out every Tuesday and Friday.