As expected, the Portland Trail Blazers have flipped Jrue Holiday to the highest bidder.

That contestant was the Boston Celtics, who traded Robert Williams III, Malcolm Brogdon and a couple of first-round picks (one protected and one unprotected) for the services of the NBA All-Defensive First Team guard. 

Seeing the massive haul the Blazers copped has improved our initial grade for the Damian Lillard trade, but what does this deal mean for the Celtics?

Yes, Holiday makes them better. But how much better? Which areas did they get worse? And does this move push them past the Milwaukee Bucks in the Eastern Conference? 

How They Got Better

At first glance, the Celtics swapped one all-time great perimeter defender (Marcus Smart) for another one (Holiday). That is true, but ending the examination there is missing the point.

We can quibble about the differences between Smart and Holiday defensively, but there is no question that the latter is the superior offensive player. Some would say Holiday is such a good defensive player that it causes people to overlook how impactful he is on the other end of the court.

Last season, when he was on the floor, Milwaukee’s overall net rating was far better (plus-13.9) than when he was off it. That was the fourth-highest differential in the league among qualified players behind Nikola Jokic (+22.3), Aaron Gordon (+18.3) and Kentavious Caldwell-Pope (+15.6) of the NBA champion Denver Nuggets.  

The best part is he’s just the type of offensive player the Celtics need. Holiday is what I like to call a mud navigator. The Celtics are at their best when they are putting the defense in a constant state of scrambling with their prolific drive-and-kick offense. They are at their worst when they run into teams that can force them to play inefficient isolation ball. 

How do those teams do that, you ask? Jayson Tatum and Jaylen Brown have grown immensely as ball handlers over the years, but there are certain teams that can make it difficult for them to dribble in the paint. If they can’t get a paint touch, they can’t ignite the drive and kick (because the defense never fully collapses). And they end up settling for long 2s.

Look at how much the Miami Heat were able to stymie Tatum and Brown during the Eastern Conference finals by gaping their driving lines and aggressively attacking their handle:

Over the last couple of years, the key to beating the Celtics has been to put their offense in the mud. That’s where Holiday comes in and why we’re now calling him their designated “mud navigator.” Holiday gives them a steadying on-ball force who can handle these aggressive defenses and steer Boston’s offense back on course. 

He’s a better functional ball handler than both Tatum and Brown. Last season, only 48 of his turnovers were lost-ball turnovers (27.9%) – the kind that comes from mishandling the ball. Meanwhile, 78 of Tatum’s (49.7%) and 68 of Brown’s (52.7%) were of that variety. 

Holiday also placed in the 79th percentile in pick-and-roll ball handler efficiency – only Brogdon and Smart surpassed that mark for the Celtics, and neither one of them came close to his volume (7.2 possessions per game, per NBA.com).

On top of that, Holiday has hit 39% of his pull-up 3s over the last three years. No Celtic from last year who attempted at least one pull-up 3 per game converted on more than 37%. All these pieces of evidence point to the fact that Holiday gives the Celtics the floor general they have been looking for. 

But just because his offense may be his most important contribution to this team doesn’t mean they won’t need his all-world caliber defense. As you’ll recall, the Celtics also acquired Kristaps Porzingis from the Washington Wizards this offseason. Porzingis is primarily a drop big man

When you run a lot of drop coverage, you want to have guards who are great screen navigators so that they can increase the degree of difficulty on the pull-up jumpers that you naturally concede.

As I’m sure you’re well aware, the Bucks have been drop coverage university over the last few years, and Holiday was their valedictorian. 

How They Got Worse

The Celtics’ top six are now Holiday, Tatum, Brown, Porzingis, Al Horford and Derrick White. That’s probably the best top six in basketball right now (all of them finished the 2022-23 season in the top 75 in DRIP).

But there are some serious question marks after that. 

It won’t be a problem in the regular season. The Celtics have spent the offseason accumulating intriguing pieces (guys like Jordan Walsh, Lamar Stevens, Dalano Banton and Oshae Brissett). But what happens when we get to the playoffs? Can any of those players turn into legitimate two-way postseason performers? 

To further complicate matters, at least two of their Super Six come with questionable injury history (Porzingis and Horford), and both of them play the same position (center). Knock on wood, but what happens if both of them go down at the same time? Who is going to adequately man the middle for them in that situation? 

Speaking of the center position, along with the loss of depth, the Celtics also lost their best per-minute defender in Williams.

Even with how impressive Holiday’s defense is, he will never be able to match the impact of an elite defensive center, which is exactly what Williams has been over the last couple of years (when healthy). Last season, Williams posted a defensive DRIP of 1.3, which ranked 11th in the entire league. And when he was on the floor, the Celtics had a defensive rating of 112.5 – good for sixth in the league among those with at least 3,000 possessions. 

Can the Celtics reach the same levels without him? And if not, does what they gained on offense make up for it? 

Where They Stand

That last pair of questions frame the Holiday move for the Celtics perfectly. Losing Williams made them worse on defense, but gaining Holiday made them better on offense.

This is basically the exact same tradeoff the Bucks accepted when they swapped Holiday for Damian Lillard last week.  

Who is better than who? Right now, that is difficult to say. The Celtics still have the assets to make other moves to address their current weaknesses. And if that happens, they may be able to gain a significant edge over their biggest rival. 

But, as it stands today, it appears that the Bucks deal to land Lillard and the Celtics trade for Holiday put these two juggernauts on a collision course for the title of Eastern Conference champion. 


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