The Milwaukee Bucks have officially pulled off a first in NBA history by signing another Antetokounmpo brother to a two-way deal, joining Giannis Antetokounmpo and Thanasis ahead of the 2025 regular season. According to Shams Charania, it is the first time three siblings have all been on active roster contracts for the same team. And while this surely is a headline for the record books, the subtext might matter even more.

The Bucks have entered a season where the stakes couldn’t be higher. A 13-year franchise cornerstone, Giannis has one year left on his contract after this season. Every win and every signing are being dissected for what they might mean about the Greek Freak’s future. That’s why Alex Antetokounmpo’s signing feels less like a coincidence and more like a calculated move. As Shams told NBA Today, the Bucks are “doing everything they can to make Giannis feel as comfortable and accommodated as possible.”

He called the signing part of a broader effort to leave “no stone unturned.” Still, Shams clarified that Giannis’s decisions are “isolated” from these moves and will ultimately hinge on the team’s play this season. In other words, the Bucks can bring in every Antetokounmpo on Earth, but Giannis will judge the front office by what happens on the floor, contrary to what some may have presumed. Brian Windhorst added another viewpoint to that effect.

After Shams reported that the Knicks and Bucks briefly discussed a potential Giannis trade in August, “some teams checked in,” Windhorst said. But Milwaukee shut it down quickly. The indication was that Giannis isn’t on the market. Not now, maybe not ever. But in a league where loyalty lasts only as long as the standings say it can, certainty is just a headline away from doubt. Because the truth is, Giannis’ future may not align with the Bucks’ championship timeline.

The Bucks have flamed out in the first round three straight seasons, despite Giannis averaging an absurd 30.4 points, 11.9 rebounds, and 6.5 assists per game. According to The Athletic, Giannis is now the second player in NBA history, after Oscar Robertson, to average 30-plus points for three consecutive seasons without winning a playoff series. That’s a stat no star player wants attached to their name. And yet, this is Giannis we’re talking about.

This is a player whose identity is built on loyalty and legacy, not quick exits. His contract extension, a three-year, $186 million deal, runs through 2027 with a player option for the 2027-28 season. He’s eligible for a four-year, $293.4 million supermax extension if he hits free agency in 2026. Which makes it even clearer that money isn’t the issue. Winning is.

Giannis Antetokounmpo said it himself on media day: “I want to be on a team that allows me and gives me a chance to win a championship… it is never going to change. I want to be among the best.” 

How Giannis Antetokounmpo and the Bucks are redefining their future ahead of the 2025-26 season

The Bucks’ preseason has been promising. They’ve won games without Giannis, experimented with new spacing, and embraced a more free-flowing offense. Giannis credited the team’s approach after their win over Chicago, saying, “Last year we had one of the best three-point shooting teams in the league, and I think this year we can even be better.”

That optimism is fueled by additions like Myles Turner, whose shooting has already made an impact. The Bucks attempted 48 threes against Chicago, hitting 20. Giannis doesn’t need to be a stretch big if the floor is stretched for him. His driving lanes are clearer, his kick-outs sharper. It’s a version of Milwaukee basketball that might finally click. Still, chemistry can’t just be a preseason word.

The Bucks’ window is shrinking, and their margin for error is thinner than ever. Even if the family reunion makes headlines, Giannis’s focus remains practical. The first quarter of this season, as Shams noted, will be “critical to see just how good or where the Bucks stand.”

And if Milwaukee doesn’t stand tall enough? Well, that’s where all the speculations grow louder.

The New York Knicks have long hovered in the background of Giannis rumors. They’ve checked in, run the math, and even discussed preliminary frameworks. But the finances are overwhelming. Karl-Anthony Towns and OG Anunoby already account for nearly $433 million in combined deals. New York’s salary cap room is tight, so even if Giannis wanted to make the jump, it wouldn’t be easy. So what’s left for Milwaukee?

The answer lies somewhere between loyalty and leverage. Giannis doesn’t bluff. He most likely won’t leak a trade request through his agent or orchestrate chaos mid-season. But he will watch closely. If the Bucks stumble again, if the chemistry fades, or even if another first-round exit threatens, the Greek Freak may decide that comfort is overrated.

For now, Giannis Antetokounmpo is locked in, both emotionally and professionally, and statistically, too. But the subtext around Alex Antetokounmpo’s signing serves as a reminder that Milwaukee is managing a relationship. And relationships, even historic ones, require wins to survive.

Whether the Bucks’ historic gamble pays off won’t be clear anytime soon. Until then, though, every post-game quote and front office decision will be read curiously. Milwaukee made history this month. What they need now is stability.