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When the Milwaukee Bucks acquired Damian Lillard from the Portland Trail Blazers, conventional wisdom was that the balance of the power in the NBA had shifted. The Bucks were immediately proclaimed not only Eastern Conference favorites, but NBA title favorites as well.

On the other side, the Blazers weren’t destined to keep Jrue Holiday for long. The veteran guard didn’t really fit Portland’s rebuilding plan, which involves several young backcourt players.

Enter the Boston Celtics. In a trade that may have tilted the East and the title odds back toward Boston, the Celtics acquired Holiday from Portland on the eve of NBA Media Day.

The trade details are:

Boston Celtics acquire: Jrue Holiday

Boston Celtics trade: Malcolm Brogdon, Robert Williams III, 2024 first-round pick from the Golden State Warriors (top-4 protected in 2024, top-1 protected in 2025, unprotected in 2026) and 2029 unprotected first-round pick from Boston

Portland Trail Blazers acquire: Malcolm Brogdon, Robert Williams III, 2024 first-round pick from the Golden State Warriors (top-4 protected in 2024, top-1 protected in 2025, unprotected in 2026) and 2029 unprotected first-round pick from Boston

Portland Trail Blazers trade: Jrue Holiday

Boston Celtics

Incoming salary ($36.9M in 2023-24) 

Outgoing salary ($34.1M in 2023-24) 

The Boston Celtics are all-in. There is no other way to describe it. Boston added nearly $3 million in salary to a roster that was already $13.4 million over the tax line.

But the Celtics had to make this move.

When the Milwaukee Bucks added Damian Lillard, Boston had to counter by adding another perimeter defender. Derrick White is excellent, but the idea of defending the Bucks with White as the only good on-ball option was worrisome.

Now, Boston has the best defensive backcourt in the NBA. And they added offensive punch to their frontcourt in their previous big trade. This is the most balanced team the Celtics have had in years, and that’s saying something considering the considerable success this team has had.

Jrue Holiday is essentially the replacement for Marcus Smart, who was traded in the deal that brought Kristaps Porzingis to Boston. Smart’s defense slipped noticeably last season, but that was likely the result of years of wear-and-tear finally catching up with him. After he gave it everything he had to win Defensive Player of the Year in 2022, Smart just wasn’t the same guy last season. White was a better defender, and not by a small margin. But that doesn’t mean replacing Smart was going to be an easy task. Far from it.

In what was considered to a be down year for Holiday, he was still first-team All-Defense. White made second team All-Defense. There simply isn’t a backcourt in the NBA that approaches what these two can do together. Add to it that they both have enough size to switch with Jayson Tatum and Jaylen Brown, and Boston is re-entering their “switch everything” days.

And that’s a massive part of the reimagining of the Celtics.

The last few seasons have seen Boston become reliant on two-big lineups. Whether it was Al Horford and Rob Williams, or Horford and Grant Williams, or Williams and Williams, or Horford and Daniel Theis, or various other combinations, the Celtics generally played with two big men on the floor.

Now, Joe Mazzulla projects to go smaller and even more five-out, but with more versatility on the floor. It’s likely that the openers for Boston will be Tatum, Brown, White, Holiday and Porzingis. Boston will switch everything with the initial foursome, with Porzingis sitting back in drop coverage, or in help position near the rim. It’s possible Mazzulla will bring back the roamer role that Williams excelled in, using Porzingis as a floater along the backline of the defense.

When they stay more straight up, the Celtics are positioned to play hedge coverages, with Holiday fighting over and around screens. His screen navigation, both on- and off-ball remains elite. The Celtics may also run chained together hand-offs, all designed around allowing the ball to be funneled to Porzingis as a shot blocker.

When Horford, who seems likely to head to a bench role because of Boston’s lack of big man depth (more on that soon!), comes into the game, Boston may straight switch everything one through five. Horford still holds up fairly well against all but the quickest of perimeter players. That type of defensive scheme versatility will make it hard to score on Boston.

The Celtics will miss Rob Williams’ rim protection, same as they are going to miss Grant Williams’ terrific positional defense. But the latter is long gone now, and the former was never a good bet to stay healthy. If Time Lord could be counted on to be healthy for most of the regular season and in April, May and June, he wouldn’t have been traded. Sadly, that’s never been a reality the Celtics were able to enjoy, and hard as it was, it’s understandable that they chose to move on.

This trade gives Mazzulla a lot more defensive versatility than he had a few days ago. On the other side of the ball, Boston also becomes more dynamic.

Holiday has always been a very good shooter. He’s good off the dribble, and excellent when he spots up. In his three seasons with the Bucks, Holiday put up 49/39/80 shooting splits. Even as his three-point attempts increased, his accuracy remained good.

When Boston traded Smart, the immediate focuses were on his defense, leadership and toughness. All fair worries, but all things Holiday will replace quite well. But the Celtics also lost Smart’s playmaking. He was the team’s best passer, and Boston had some questions, even with Tatum taking on more of the creation role.

Now, Mazzulla has options. Tatum is still going to have the ball a lot, as will Brown. They are the engines that make the Celtics go. White will get a fair number of touches too. But, when necessary, Holiday is more than capable of running the show.

It’s fair to expect that the Celtics offense might be a little bumpy to open the season. They’re adding in two new players, both of which are used to having primary or secondary roles in their team’s offense. It’s going to take a little while for that pecking order to figure itself out. But eventually, Holiday will be Boston’s fourth option, and not many teams have a player as good as Holiday in that slot.

There’s some additional pressure on Payton Pritchard now. He wanted a change, and he’s going to get it as the Celtics third guard. He’s not going to be asked to replace Brogdon’s Sixth Man of the Year production, but Pritchard has to provide shooting, some playmaking and enough defense to be playable.

But the offensive and defensive fit, and roles are the least worrisome parts of this trade. The most worrisome portion of this trade is the Celtics frontcourt depth. Even if the team will play smaller lineups more often, and even factoring in Williams’ injury history, Boston is thin up front.

It’s pretty much Porzingis and Horford now. And Porzingis has a lengthy injury history of his own, and Horford is 37 years old. If Porzingis gets hurt again (he did deal with a case of plantar fasciitis over the summer) or Horford falls off (less likely, as he’s remained rock solid), Boston will be in trouble.

Luke Kornet has generally been solid for the Celtics when called upon. But he’s much more of a fourth or fifth big than a third big. Boston is reportedly signing Wenyen Gabriel. He’s also a solid player, but again, more of a fourth option. Brad Stevens might not be done seeking out additional big man depth. Boston is still sitting on a $6.2 million TPE. That could come into play at some point down the line.

The last thing we want to cover is Holiday’s future beyond this season. He has a $39.4 million player option for 2024-25, but it’s unlikely Holiday will play on that number next year. He’ll either opt out and head into free agency, or he may work out a long-term extension with the Celtics. It’s already been reported both Holiday and Boston want to make this a long-term partnership.

We’ll cover Holiday’s extension possibilities in depth in a future Next Contract series. For now, it seems likely Boston will do what they can to get Holiday signed to a new deal. Ideally, they’d bring his 2024-25 salary down by a considerable amount, while adding three or four new years to his deal.

As it stands right now, if Holiday picked up his option, Boston would basically be in the luxury tax for the 2024-25 season with just five players with Tatum, Brown, Porzingis, White and the newly added Holiday. Add in the guaranteed salaries for Horford and rookie Jordan Walsh, and the Celtics will be well into the tax next season.

But that’s the cost of trying to win a title in the NBA. And the Boston Celtics are all in on winning Banner 18.

Portland Trail Blazers

Incoming salary ($36.9M in 2023-24) 

Outgoing salary ($34.1M in 2023-24) 

Much like we did with the trade with the Milwaukee Bucks and Phoenix Suns that delivered Holiday to Portland, we’re going to keep this relatively simple.

Malcolm Brogdon probably won’t be in Portland very long. He’s probably going to be traded before long. Brogdon may stick around longer than Holiday, only because camps are starting in a few days. But the Trail Blazers are going to keep things moving and will flip Brogdon for even more additional assets. Because of that, we’re not going to focus on Brogdon’s fit with the Blazers at all. It’s simply not going to matter.

Rob Williams, on the other hand, is a bit of a curious addition, as Portland previously acquired Deandre Ayton as their center of the future. Ayton and Williams aren’t a workable combination, so this is a depth and “Why not?” type of double-down acquisition for Portland.

Williams is an athletic marvel. He catches and dunks lobs that most guys wouldn’t get fingertips on. Williams will block shots from out of nowhere, and regularly go back up and block the putback too. He’s also a ferocious finisher around the rim. His rebounding is greatly improved and he’s also a terrific passer.

On the downside, Williams is also a good bet to miss considerable chunks of each season. The healthiest he’s ever been was in the 2021-22 season. Just as Boston was morphing into a juggernaut, Williams tore his meniscus, missed the end of the regular season, some of the playoffs and never looked quite right when he got back late in the Celtics 2022 NBA Finals run.

But this is the kind of mini gamble Portland can make right now. If Williams gets healthy, he’ll team with Ayton to give the team 48 minutes of very good center play. As the Blazers grow, Williams will become an important piece because of his defense.

If nothing else, Williams is another tradable asset. He’s on a great contract. If Portland decides they don’t need him, it’s a lock that some contender will happily make a deal to pick up Williams, in hopes that they can keep him healthy.

Last, but far from least, Portland added two more first-round picks in this deal. The top-4 protected pick from the Golden State Warriors is close to a lock to convey this year. Unless everything craters for the Warriors, the Blazers will get a non-lottery pick. If Golden State does fall apart fully, Portland will see that pick flip to top-1 protected in 2025. If by some change the Warriors are a two-year mess, the Trail Blazers will get an unprotected pick in 2026.

The real get is the 2029 first-round pick from the Celtics. By the time that pick comes due, it’s impossible to predict what Boston will be. Both Jrue Holiday and Al Horford will likely be retired. Kristaps Porzingis will be 34 years old and, if we’re being honest, probably long gone from Boston.

Jaylen Brown will be in the final year of his yet-to-start super max extension, and Jayson Tatum will be in Year 4 of his incoming super max extension. On paper, Brown and Tatum in their early-30s should be enough to keep Boston in contention. But a lot can, and will, change between now and then.

Much like they did in the deal with the Bucks, the Trail Blazers added another mystery box pick. If their young core proves ready to win in the next two or three years, Portland will have additional assets to use in trades to supplement that core. Just as Boston did in this deal. As it always has, the NBA transaction wheel rolls ever onward.