Should Boston Celtics pursue All-NBA defender on trade block?

Well, the Milwaukee Bucks, who already projected themselves as one of the Boston Celtics’ biggest threats coming into the 2023-24 season, pulled out the big guns when they acquired Damian Lillard from the Portland Trail Blazers, as reported by ESPN’s Adrian Wojnarowski, in exchange for Jrue Holiday, among others.

As Wojnarowski would later note, the Trail Blazers have no interest in keeping Holiday, seeing how trading Lillard signaled that they are starting their rebuild.

So, factoring in that the Celtics have a distinct lack of Marcus Smart on their current roster, Holiday would replace a lot of what Smart brought to the table while also bringing a little more shot creation and better decision-making. So does that mean the Celtics should snag the former Bucks star the first chance they get?

Well… it’s complicated.

Why a Jrue Holiday trade to the Boston Celtics isn’t an easy choice

Holiday’s resume is impressive enough that were the Boston Celtics to simply add him to the roster with no strings attached, it would be hard to see why they wouldn’t. Holiday is a two-time all-star, an NBA champion, and has made an NBA All-Defense team five times. If that’s not enough to sell you on him, remember that back in 2018, Lillard had one of his very worst playoff performances over an entire series against the New Orleans Pelicans in 2018. Lillard averaged 18.5 points while shooting 35.2% from the field and 30% from three in a four-game sweep, per ESPN.

And who was responsible for Dame Time suddenly going Lame Time? Jrue Randall Holiday.

Knowing that Holiday proved to be to Lillard what Andrew Wiggins was to Jayson Tatum during the 2022 NBA Finals, and with Smart no longer in the picture, there would be some sense of comfort in the Celtics’ backcourt if Holiday made his way to Beantown. That is if he wasn’t paid like a franchise player.

While the Boston Celtics would have Malcolm Brogdon to potentially offer the Trail Blazers for salary cap matching purposes, him for Holiday straight up doesn’t work. Brogdon will be paid a hefty fee of $22.5 million this season, but Holiday, by contrast, will be paid upwards of nearly $37 million when you combine his contract with likely incentives. So, it will take more than just Brogdon to get it done, and the Celtics can’t include Payton Pritchard, Sam Hauser, and Luke Kornet to make a trade feasible from a financial standpoint.

Trading for Holiday would require Brogdon and one of Al Horford or Robert Williams III, along with others, to make a trade work. The Boston Celtics have tried like crazy to avoid the league’s second luxury tax apron, so to continue going that path, others would have to go with Brogdon and Horford/Williams. Despite Holiday’s appeal, stripping away that much depth for him is a risky maneuver. The Celtics’ frontcourt depth is already a tad shaky, and removing one of Horford or Williams puts them on thinner ice.

Now putting the money factor aside, the Boston Celtics would also have some appetizing assets to offer Portland. They have all their first-round picks on top of the Warriors’ first-round draft pick in 2024, thanks to the Kristaps Porzingis trade. Since Holiday could potentially expire after next season, getting that in exchange for him would be an almost ideal return for the Trail Blazers. But that also serves as another possible red flag should the Cs acquire him. Trading multiple assets for someone approaching their mid-30s who could leave in a year is not smart business. Why do you think James Harden has still remained a Sixer after all this time?

And yet, putting aside the financial implications and the risk of him suddenly departing, Holiday would be fourth in the Celtics’ pecking order, provides pretty much everything they lost in Smart and then some, and who knows, maybe he’d be open to a discount if he grows to love Boston.

So, should the Boston Celtics bring in Holiday? Well, if the Trail Blazers were to do what former Celtic Evan Turner advised them to do with their new player, then of course.

But trading that much depth for Holiday, who is 33 and is eligible for another expensive extension next season, may not be the best alternative to simply keeping things the way they are, as explained by Dan Greenberg.

With Miami whiffing on Lillard, the Sixers still dealing with the James Harden fallout, and the Bucks shaking up their core to the extreme just as the season’s about to start, the Celtics can rest easy knowing that at this current moment, there’s much more uncertainty going around their competitors in the East itself than with them.

However, should Brogdon prove to not be the same player he was last year, and if Father Time finally hits Horford in full force, this is a prospect that the Boston Celtics may have to keep in the back of their minds. But they must be wary that if Holiday comes up on their radar, their window to get him will be quite small.