In the summer of 2007, Danny Ainge looked at a 24-win Celtics team and decided incremental improvement wasn’t enough. Within weeks, Boston traded for Ray Allen and Kevin Garnett, sacrificing young players, draft picks, and future flexibility in pursuit of a championship window. The gamble delivered Banner 17 one year later and became one of the defining moves in franchise history.

Nearly two decades later, the Celtics once again find themselves linked to a transformational superstar. This time, the name at the center of the conversation is Giannis Antetokounmpo. Earlier this month, Bill Simmons reported that Boston had unexpectedly entered the Giannis sweepstakes despite previous indications that the franchise planned to sit out the race. Simmons later doubled down on that reporting, saying he had heard Boston had already submitted an offer to Milwaukee.

“I think they dove in. From what I heard, they made an offer in the past week, a couple of days before I mentioned it on Thursday. I don’t know what the offer was,” Simmons shared on his podcast. “And I don’t know who’s in it, but they had their hat in the ring, which I was really surprised by, as I said on Thursday, because I thought they were sitting it out.”

The comments marked a significant shift from Simmons’ earlier stance. Just days before, he had maintained that Boston was effectively out of the running. “I thought Boston was out of this. I know Boston was out of this,” Simmons said on a previous episode before adding that the Celtics appeared to be “playing a little possum” and had become active participants in the Antetokounmpo sweepstakes.

Any serious Boston offer would likely require a franchise-altering decision. Jaylen Brown’s contract is one of the few pathways to matching Antetokounmpo’s salary, while the Celtics continue to navigate the financial restrictions that come with operating deep into the NBA’s second apron. With Giannis also eligible for a massive extension, any deal would reshape both organizations for years to come.

Meanwhile, insider Zach Lowe added, “I don’t think they (Celtics) were ever out. The safest bet is always inertia, right? The safest bet is that we know that the nucleus we have works really well, and there’s some degree of risk in shaking that up for a 31-year-old who’s been injury-prone, and we’re going to have to sign him to a ginormous extension.” He added, “It’s a big pivot for a team that has a pretty large window now of being one of the best teams in the NBA when everyone’s healthy.”

Part of the league-wide fascination stems from Antetokounmpo’s own comments about balancing loyalty with championship aspirations. Earlier this year, the Bucks star said, “Before loyalty, winning comes first. We are judged on winning. I’m a winner. I want to win.” He later added, “If there is a better situation for me to win the Larry O’Brien, I have to take that better situation.”

Lowe suggested Boston’s disappointing finish could make a pursuit of Antetokounmpo more appealing than it may have seemed earlier in the offseason. He also believes the team may see limited competition for Giannis, making a trade pursuit more attractive because fewer rival teams are seriously bidding for him.

Milwaukee’s situation also helps explain why trade speculation continues to grow. The Bucks possess one of the league’s oldest cores, have limited draft capital remaining from previous win-now moves, and face mounting pressure to maximize value if Antetokounmpo ever signals a desire for a fresh start. For that reason, rival executives continue monitoring the situation closely even without any indication that a deal is imminent.

The Miami Heat are still a name in the Giannis Antetokounmpo trade conversation

Miami has lingered around the Antetokounmpo conversation for months. Reports around the trade deadline suggested the Heat were among the most aggressive suitors, with Milwaukee opting to revisit its options during the offseason rather than rush into a franchise-defining decision.

Now, the Heat have interesting packages to get Antetokounmpo. Miami’s pitch to Milwaukee revolves around a young trio featuring Tyler Herro, Kel’el Ware, and Jaime Jaquez Jr. Meanwhile, they are also prepared to attach a hefty stash of future assets. The package reportedly includes 3 unprotected first-round picks, with 2026, 2029, and 2030 emerging as possible selections. Pick swaps in the years between those choices have also entered the conversation.

Several league analysts have described Miami’s proposal as one of the stronger asset-based packages currently available. However, unlike a hypothetical Boston offer built around an established All-NBA player such as Brown, the Heat’s proposal is centered on younger talent and future draft flexibility.

Moreover, Miami could toss in extra pieces to balance the books and add more appeal. Names like Pelle Larsson and Kasparas Jakucionis have surfaced as potential additions. Altogether, the proposal blends proven scoring, promising youth, and long-term flexibility. They are giving the Bucks a chance to reload while cashing in on their 10-time All-Star with a massive return.

For now, Antetokounmpo remains a member of the Bucks and there is no indication that a trade is imminent. However, Simmons’ report that Boston had submitted an offer to Milwaukee dramatically changes the landscape of the conversation. Miami may have spent months positioning itself as a potential destination, but if the Celtics are truly willing to discuss a package centered around a player of Jaylen Brown’s caliber, the Giannis market could look very different than it did just a few weeks ago.