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The Celtics should absolutely trade for Jrue Holiday

It would be a risk, but with Holiday reportedly on the block, the Celtics would do well to go after him

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Boston Celtics v Milwaukee Bucks Photo by Patrick McDermott/Getty Images

In by-far the biggest news of the day, Jrue Holiday is available for trade! I wonder if the Celtics should go after him. We definitely should, right? Hmm… how about this trade? That draft pick goes there… carry the four, Pritchard can go home… Prit-ch-aaard ca..n g- hooooooooo…

(Warning: Celticsbrain overloading, consciousness slipping)

Oh, The Milwaukee Bucks have traded for Damian Lillard? Whatever.

That news was so seven hours ago. Lillard made his way out of Portland and will conceivably be tasting artisanal cheeses by early next week. He dropped a farewell single for Blazers fans, creatively titled “Farewell,” and early returns have the Bucks as the new favorites to win the NBA Finals… and that’s that. Pack it up, move on, we’re done here, right?

In all seriousness, my illustrious colleague Jack Simone wrote a super-hot-fire analysis of what the Bucks-Lillard marriage will mean for the Celtics, and if you’re wondering, go check it out! But I’m here to discuss the newer, slightly smaller elephant in the room: Jrue Holiday.

Holiday, the two-time All Star, three-time All-Defensive First Team and one time second-best-guy-on-a-title-team was just traded to the Blazers along with a 2029 first round pick to pry Lillard from Portland.

But Holiday is a 33-year-old point guard, a position the Blazers have had no interest in messing once they landed Scoot Henderson in this year’s draft. By all accounts, the Blazers capital-L Love Scoot, so why would they trade for Holiday?

ESPN’s Adrian Wojnarowski quickly addressed this obvious contradiction.

“The Blazers remain engaged elsewhere on deals and will are expected to immediately engage contending teams on trade talks to move on Jrue Holiday, sources tell ESPN,” Wojnarowski said on X this afternoon. “Portland is committed to its young group of talented guards.”

I don’t know about you, but upon hearing that a topflight player is immediately available, my Celticsbrain instantly thinks of reasonable ways to get that person on the Celtics.

If only it were so simple.

Of course, in a vacuum, every team and fan would love to have Jrue Holiday’s services. But he’s also on the back 9 of his prime, on the last year of his deal and will thus almost certainly want an extension wherever he ends up. Do the Celtics really want that on the books?

Potentially, even more troubling is who and what the Celtics may have to give up to get Holiday, and with the roster looking so positively loaded as is, do we really need to mortgage the farm for another contributor?

All of these questions are swirling around in my Celticsbrain, so I thought we’d parse the parameters of what a trade could look like, with relevant commentary included. Then we can all decide if it’s actually a good idea, and call Brad Stevens on speakerphone to let him know our decision. Sound good? Ok, break.

Boston Celtics v Milwaukee Bucks Photo by Patrick McDermott/Getty Images

Question 1: What does trading for Holiday cost?

Holiday’s market—like most markets in human society after the fall of the Berlin Wall—will be dictated by relevant competition. So which contenders could be bidding alongside the Celtics?

Two words: Miami Heat. They just lost out on the Lillard, probably because their offer was like trying to trade a disassembled 2002 BMW for a lightly-used Ferrari. But they make the most sense and then some to go after Jrue, who feels like Heat Culture waiting to happen.

Holiday is not the same tier of player as Lillard, but their offer is probably the same-ish: two first round picks, maybe a swap and Tyler Herro, along with whatever filler they’d like to include.

Can the Celtics beat that? I think so, as Malcolm Brogdon and a more lucrative pick-package is definitely in the cards, as well as a shockingly large war chest of second round picks acquired through a bunch of super random trades last year. Maybe Payton Pritchard even gets to go home to Portland, which I think would make everyone happy.

But you start to lose me when names like Robert Williams III and (shivers) Derrick White get brought up. Most of the reason I’m so interested in Jrue is because of how glorious a backcourt he and White would be. The sheer amount of defense would be staggering. With Porzingis arriving, I could be convinced to include Williams in a trade, but White is a non-starter.

Other possible destinations off the top of the dome: the 76ers, Knicks, Magic, Raptors, and Warriors could all throw out an offer, but the Heat feel like the main contender. Nevertheless, I think the Celtics have a real offer if they’re willing to shell out picks.

Question 2: Is Holiday the player really worth all that?

In the immortal words of John Wick, “yeah.”

Holiday’s true value doesn’t come out in his counting stats, which aren’t by any means bad. He’s hovered around 18-7-5 for pretty much his entire career, but his real impact comes in how he’s perceived by his opponents.

In The Athletic’s yearly anonymous poll of NBA players, Holiday jumped off the page. His peers voted him the league’s best defender by a landslide, as well as the NBA’s most underrated player. All the while, Holiday is a certified gamer, routinely elevating his game in the playoffs and annihilating inferior defenders.

He murdered the Celtics bench in the regular season last year, mercilessly dropping 40 on their heads, before eviscerating Indiana with a career-high 51 on insanely efficient shooting. He once lit up the Trail Blazers (his current team) so hard that he and Anthony Davis accidentally scored the most points ever by a pair of teammates in a playoff game. In short, he can hoop.

On the Celtics, Holiday creates positively outrageous lineup flexibility that borders on death-lineup levels. He and White could play with Jaylen Brown, Jayson Tatum and Al Horford to go small like the world has never seen.

White could be replaced by Robert Williams III and Al slide out for Porzingis, and suddenly morph into the sickest big lineup ever. Holiday should work perfectly with what the Celtics want to do, both offensively and defensively.

Question 3: That’s all well and good, but what about that extension?

That is the potentially $130 million question. Holiday will probably want a Fred VanVleet-level deal from wherever he goes, though the Celtics wouldn’t be required to pay him anything more than the last year of his deal plus the player option he could pick up. It would however be an exceedingly awkward situation if Holiday feels he is being undervalued.

I’m also not completely out on the idea of paying Holiday a three-year extension. It might feel rich for someone his age, but Holiday is such a cerebral player that he might age pretty well. This might be the time to get Holiday locked in before the second apron makes paying more than two guys extremely difficult.

I won’t lie, it’s not like this is a financial slam dunk. But it’s possible.

Final Determination:

I think seriously pursuing Holiday with real draft capital is worth the risk of his age, even with an extension on the books. Do we all agree? If so, I’m calling Brad. Let the point guard arms race begin!

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