Celtics 'all-in' on Giannis trade: 3 massive questions Boston must answer

When the Boston Celtics captured Banner 18 in 2024, the New York Knicks acted swiftly. A day before the draft, news broke that their rival franchise from the Big Apple was sending five first-round picks to the Brooklyn Nets for Mikal Bridges. With the Knicks now standing atop the NBA summit, the Celtics seem prepared to duplicate that combination of boldness and urgency.

According to a flood of reports that began at nearly 3:30 a.m. on the East Coast, Boston is willing to offer Jaylen Brown to emerge as the winner of the Giannis Antetokounmpo sweepstakes.

As ESPN's Brian Windhorst put it, they are "all-in."

"They were very cautious about putting Jaylen Brown in an official firm offer. I believe they have," said Windhorst in an appearance on Get Up on Monday. "Jaylen Brown is on the table, and Jaylen Brown could get traded for Giannis Antetokounmpo in the short term."

3 critical questions about the Celtics' pursuit of Giannis

Jimmy Haslam isn't just the co-owner of the Milwaukee Bucks. He also owns the NFL's Cleveland Browns. That franchise recently parted with superstar Myles Garrett. The return centered on not just getting draft picks, which they received three of, but also acquiring a player they could be excited about moving forward with. That individual is 25-year-old, two-time Pro Bowler Jared Verse.

It appears that Haslam may aim to go in a similar direction in an Antetokounmpo trade. The difference is that Brown turns 30 in October. The Bucks have the No. 10 pick in this year's draft. That positions them to land a top prospect in a loaded lottery. However, their roster isn't built to support a 30-year-old star. If it were, Antetokounmpo wouldn't be trying to leave.

The combination of Brown and a top-10 pick in this year's draft is an unorthodox foundation to build around. Milwaukee could reroute the former Finals MVP at a later date, but he's a strange fit in a post-Giannis era. Nonetheless, it appears that, for now at least, he would be headed to Brewtown if Boston has the winning bid.

That brings us to question No. 1: What if the Celtics don't close the deal?

Teams around the Association were reluctant to have their identity and offer out there for this exact reason. The organization can scream from the mountains that this is fake news, and that there was never any intention of breaking up its star tandem. However, there's too much smoke around the situation to trust that.

Instead, as Windhorst noted, Brown's favorite season in Boston was likely his last one there.

That could mean a trade for Trey Murphy III of the New Orleans Pelicans, or a scenario only being discussed privately. However, after a decade with the Celtics, it appears that it's time to say goodbye.

The combination of Brown and Tatum led one of the most successful eras in the illustrious history of the NBA's original monarchy. They raised a championship banner to the TD Garden rafters and made appearances in the Eastern Conference Finals feel like an annual tradition.

Last season, the five-time All-Star inserted his name into the MVP conversation while guiding the organization through a period of uncertainty. However, whether it's the temptation of adding a top-five talent, concerns about how Brown would respond to no longer having his own team, or a combination of the two, the outlook on him donning a Celtics jersey next season is bleak.

That brings us to question No. 2: Who and what else will Boston have to give up?

Brown is the best player or pick that's reportedly being offered. Brad Stevens will still have to cough up more. That includes draft capital.

Parting with the No. 27 pick in this year's draft -- as many intriguing prospects in that range as there are -- doesn't feel like a painful sacrifice. Instead, the question may be whether or not the Celtics can keep Hugo Gonzalez.

Stevens raved about the rookie wing at the end of his first NBA campaign. The franchise that selected the 19-year-old standout from Real Madrid late in the first round last year would surely love to hang on to him. However, for all of the promise about what the future might hold for Gonzalez, even with Brown topping anything the Miami Heat can offer, his inclusion is unlikely to be a deal-breaker.

Boston isn't operating like a team that is prepared to walk away from the table. And the Celtics would still have a trio of talented young wings in Baylor Scheierman, Jordan Walsh, and Ron Harper Jr. They could also move forward with Sam Hauser. However, the veteran sharpshooter could find himself in a trade to fortify the center position or another area on the roster.

And then there's question No. 3: Will the Celtics reset the repeater tax if they trade for Giannis?

This author leans yes. They don't have to stay under the luxury tax this league year to accomplish that. And acquiring Antetokounmpo constitutes that big swing they'd want to take after resetting it. However, they'd still be in a prime position to do so now. They may not want to pass that up.

After all, the roster is in pretty good shape. And they could still find a partner to form a potent 1-2 punch with Neemias Queta at center while remaining under the luxury tax.

Boston would suddenly be built around a star recently removed from an Achilles tear and another who turns 32 next season and has significant durability concerns. That could spark urgency and the motivation to put off resetting the repeater tax. However, even with Antetokounmpo flanking Tatum, that seems like the less likely outcome.

The Bucks might be compelled to accept more draft capital from the Heat, including the No. 13 pick this year. Either way, it appears that Brown's time with the Celtics is about to be up.

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