Should the Boston Celtics go all in on a Giannis Antetokounmpo pursuit? Before we even weigh the pros and cons, let’s start with a series of unassailable truths:
1. When your season ends in disappointment three times in a four-year span — even if there’s a title campaign wedged in the middle — it’s absolutely fair to take a step back and evaluate all paths forward. It would be front office malpractice if the Celtics did not at least ponder the availability of a two-time MVP.
2. One of the most endearing qualities of a well-run team is having the necessary assets to pursue a big-ticket player whenever they become available. And it’s rare.
Former president of basketball operations Danny Ainge used to talk a lot about being ready for those types of moments, when a team pushes all their chips in. It led to pursuits of everyone from Kevin Garnett to Kyrie Irving. The Celtics have a rare combination of assets and infrastructure that can attract a player of Antetokounmpo’s stature. Only a handful of teams can truly get in on that bidding.
3. Brad Stevens is a GM ninja. He moves in silence. If something is rumored, it’s usually not happening.
From the Derrick White midseason addition in 2022 to the jaw-dropping swap that sent Marcus Smart out in exchange for Kristaps Porzingis to kickstart the 2023 summer overhaul, Stevens’ trade transactions typically come out of left field. Proceed with caution.
Now, the Giannis question.
Imagine hopping in a Time Machine to, let’s say, 2017, when poor Aron Baynes was risking his body to prevent Antetokounmpo poster dunks and Celtics fans were trying to convince themselves that Semi Ojeleye could be a Giannis Stopper. (We still believe!) Ainge might have traded a decade worth of first-round picks and three of his children to acquire Antetokounmpo at that point.
We spent most of the 2010s fretting how Kelly Olynyk went two picks before Antetokounmpo, even if Olynyk remains a Celtics legend for that Game 7 against the Wizards.
But it’s 2026. Olynyk is 35 now (but still chasing a title with the Spurs this season). And Father Time headlines our list of cons when it comes to any potential Antetokounmpo pursuit.
1. Shrinking the window
Antetokounmpo will turn 32 early in the 2026-27 season. While it’s not unprecedented for stars to win rings past that age — Michael Jordan’s second three-peat came after 32, and Stephen Curry broke the hearts of the Celtics in 2022 at age 34 — it’s also fair to wonder how his body will hold up over the next half decade while he’s on a maximum deal.
Despite playing just 36 games this season, Antetokounmpo’s basketball odometer eclipsed 30,000 total minutes. Every one of his collisions feels like a car wreck.
He finished third in MVP voting two seasons ago, so we don’t want to overstate the age concerns. But an Antetokounmpo pursuit does seem to suggest a finite window.
2. Same cap concerns, less wiggle room
What the Celtics and the rest of the NBA are trying to figure out at the moment is whether you can build a roster centered around two max-contract superstar players and still have enough money to build out the depth necessary to thrive.
The Celtics, having dipped below the tax this past season, have a clear pathway to resetting repeater penalties with the current core, all without necessarily sacrificing being a contender. An Antetokounmpo addition, and the limited window it affords, seemingly would be better embraced by a team that can splurge immediately.
The Celtics can certainly do that with existing exceptions, but it’s going to be a super costly roster with limited pathways to hitting the reboot button.
3. Risk management
One more unassailable truth here: The combination of Jayson Tatum and Jaylen Brown has won a title together while enjoying an absurd amount of playoff success together.
Stiff-armed early in their title pursuits, the Jays got over that hump together in 2024. Call us hopeless romantics, but we’d love the storyline of them overcoming a new batch of obstacles to reach the mountaintop again. They’ve proven they can be a title team with the right pieces alongside.
Are we sure an Antetokounmpo/Tatum combo works? Talent is king and pairing two top-five players in the NBA is undeniably intriguing. But you’re introducing a whole new level risk to a team that might have safer pathways to jumpstarting the next title pursuit.
4. Overhauling the culture
Even if Myles Turner overstated Antetokounmpo’s plane tardiness, a Brown-for-Antetokounmpo swap dramatically overhauls the leadership dynamic in place in Boston.
Brown, thrust into the lead role this past season, didn’t just thrive on the court with a season worthy of MVP consideration. He also embraced the youngest players on the team and accelerated their development. Don’t take for granted what Brown means to not only the Celtics, but the city of Boston, too.
The counterargument? It’s Giannis. He’s literally a Freak. Fortune favors the bold. If you feel this core has maxed out its potential, and if the landscape of the NBA — with two juggernauts blossoming out West — leaves you fretting the path to title contention, then pushing all-in for Antetokounmpo is an intriguing short-term swing.
We’ll also relent that Brown’s trade value will never be higher. He’ll turn 30 at the start of the new season, can dig in on a big-money extension moving forward, and proved that he can be the focal point of a top contender.
We simply wonder, if the Celtics decide that a pivot on the core is necessary, if getting younger and more cost-efficient is a better long-term path forward than taking on the Antetokounmpo risks.
