Giannis Antetokounmpo’s Future in Milwaukee Is Uncertain

Giannis Antetokounmpo carried around a small, black portable fan, which looked minuscule as it whirred in his 12-inch-wide hands. He was trying to counteract the hot sun at a hillside mansion as he watched his youngest brother, Alex Antetokounmpo, pose for photos near a basketball hoop overlooking Los Angeles for an ad campaign.

“Alex, the eyes,” Giannis said. “Eyes of the tiger right there, and then you mix it in with a smile.”

Giannis turned and grinned at a group of about a dozen people watching. He has been coaching Alex for most of his life. When Giannis began his N.B.A. career with the Milwaukee Bucks at 18, he soon brought his family out of poverty in Greece to live with him. Alex was 12 years old.

“Sometimes I think I get annoying to him,” Giannis, 28, said later, though Alex, 21, shows no signs that that might be true. Giannis added: “He could be doing idiotic stuff, stupid stuff, but he’s going through a path that I’m really proud of him.”

As Giannis ascended to N.B.A. superstardom — he’s won the Most Valuable Player Award twice and is the best player on a championship team — he strove to bring his family along for his journey. Three of his four brothers have played professionally in the United States.

But over the past three years, he has brought them along for what he hopes can be a more lasting endeavor: taking ownership of their money and his future. A few months ago, Antetokounmpo launched Ante, Inc. to house the brothers’ projects and investments. It’s about Giannis’s life beyond basketball, though basketball still matters to him — a lot. In a few weeks, he will be eligible for a three-year extension worth about $173 million, but he doesn’t plan to sign one just yet.

“The real question’s not going to be this year — numbers-wise it doesn’t make sense,” Antetokounmpo said. “But next year, next summer it would make more sense for both parties. Even then, I don’t know.”

He added: “I would not be the best version of myself if I don’t know that everybody’s on the same page, everybody’s going for a championship, everybody’s going to sacrifice time away from their family like I do. And if I don’t feel that, I’m not signing.”

This approach and an increased focus on business investments with his brothers are part of Antetokounmpo’s evolution as he has begun to understand his own ambitions and goals more deeply.

“From 2020 to 2023, people think I’ve taken a large jump on the basketball court, but I think I’ve taken 10X jump off the court,” he said.

‘I gave everything.’

It started in the spring of 2020 when the world shut down because of the coronavirus pandemic. It wasn’t clear what would happen to players’ salaries or endorsement deals with the season in flux. He began to think of ways to diversify his sources of income.

“We were sitting in the house. OK, now what?” Antetokounmpo said. “Basketball is taken away, what do I have?” He downloaded a stock trading app and started investing on his own for the first time. He began to reach out to successful people from other industries for advice and mentorship.

It was an eventful year for him, which may have contributed to his interest in growing his income. His oldest child, Liam, had been born that February, and he had won his second M.V.P. Award, for the 2019-20 season, which the Bucks finished by losing in the Eastern Conference semifinals at the N.B.A.’s quarantined campus at Disney World.

A few months later, Antetokounmpo signed a five-year, $228 million extension with the Bucks. But something was not right. He felt numb, and did not know why. He told the Bucks that he did not want to play basketball anymore.

He had felt that way before. During his rookie year, he missed his family so much that he had insisted that the Bucks figure out a way to get them to Milwaukee, even threatening to go back to Greece if the team would not do it. He and his brothers had shared beds growing up. When Antetokounmpo left Greece for the N.B.A. draft in 2013, he said his father, Charles, told him: “No matter where you go in this world, doesn’t matter, don’t worry about that, I’ll find you. I love you, my son. Go have a great season.”

“And I remember my mom was crying,” Giannis said. “I left. And then when I came here it wasn’t the same. I was in the hotel. It was the first time I felt lonely in my life.”

Alex said the siblings are “pretty much each other’s best friends.”

When Giannis felt down during the 2020-21 season, he was reassured when he told his older brother Thanasis about his doubts. By then, Thanasis was playing for the Bucks, too, and said that if Giannis was not happy he would leave with him.

“I would have walked away in 2020,” Giannis said. “I care about joy and happiness. I care about my kids.”

The Bucks recommended he speak to a sports psychologist, so Antetokounmpo tried it. Doing so helped him find ways to cope with the stress and pressure he felt. He rediscovered joy in playing basketball, and the Bucks won a championship that season.

“I think it’s the best feeling that I’ve felt so far in basketball,” he said.

He wants it again.

The Bucks lost in the first round of last season’s playoffs, winning only one game against the Miami Heat as Giannis worked through injuries.

Milwaukee fired its coach, Mike Budenholzer, and hired Adrian Griffin, who had been an assistant coach for the Toronto Raptors. That change, Antetokounmpo said, is part of why he is unsure if he’ll sign an extension.

“You’ve got to see the dynamics,” he said. “How the coach is going to be, how we’re going to be together. At the end of the day, I feel like all my teammates know and the organization knows that I want to win a championship. As long as we’re on the same page with that and you show me and we go together to win a championship, I’m all for it. The moment I feel like, oh, yeah, we’re trying to rebuild —”

He paused briefly before continuing.

“There will never be hard feelings with the Milwaukee Bucks,” he said. “I believe that we’ve had 10 unbelievable years, and there’s no doubt I gave everything for the city of Milwaukee. Everything. Every single night, even when I’m hurt. I am a Milwaukee Buck. I bleed green. I know this.

“This is my team, and it’s going to forever be my team. I don’t forget people that were there for me and allowed me to be great and to showcase who I am to the world and gave me the platform. But we have to win another one.”

He is halfway to his goal of playing 20 N.B.A. seasons, and he said he would like to spend them with one team, the way Dirk Nowitzki, Kobe Bryant and Tim Duncan did.

“But at the end of the day, being a winner, it’s over that goal,” he said. “Winning a championship comes first. I don’t want to be 20 years on the same team and don’t win another championship.”

He didn’t mention any motivation for winning another championship outside of his competitive fire. But the cultural relevance that comes with winning can also elevate his growing off-court profile.

‘We came from nothing.’

Giannis couldn’t help but launch into a sales pitch as he sat in the living room of the home where he and Alex were doing the photo shoot. He was hyping a pain-relieving balm made by a company called Flexpower, which the Antetokounmpo brothers partially own. He has always considered himself to be a great salesman, back to when he was a child trying to help his parents sell sunglasses on the street in Athens.

During the photo shoot, Giannis flitted around like a proud mother hen, beaming at Alex. Working with the company was Alex’s idea.

“I knew you when you were a baby!” Giannis said, holding his hands out as if rocking a baby.

Later, Giannis pondered when it was that he started thinking of Alex as an adult.

“Might be today,” he said.

Four of the brothers are listed as co-founders on the Ante, Inc. website, but Giannis is the chairman. They have different roles, by virtue of their personalities. Alex describes Thanasis, 31, as very driven and bold in his style. Kostas, 25, has a quieter personality, but Alex said he excels at brainstorming.

Giannis involved his brothers in discussions about his new Nike contract, which he said he negotiated himself this summer. One of his earliest investments was in the Milwaukee Brewers, in 2021. The brothers have invested in a candy company, a nutritional company and a golf team co-owned by Venus and Serena Williams and Serena’s husband, Alexis Ohanian. They have a production company in the works, like so many other N.B.A. players do.

This year, Giannis became a co-owner of some funds with Calamos Investments, whose chief executive, John Koudounis, is of Greek descent. The joint venture donates 10 percent of its profits to financial literacy organizations.

“He spent a lot of time talking about how he wishes that he had known about investing earlier,” said Jessica Fernandez, Calamos’s chief marketing officer. Antetokounmpo doesn’t manage the portfolios, but he does pepper those who do with questions about why and how they choose certain stocks.

Earlier this year, the Antetokounmpo brothers joined the ownership group of Major League Soccer’s Nashville SC.

“We came from nothing,” Antetokounmpo said. “And sitting in the owners’ suite with the other owners and enjoy the game, cheering for our team. Our team. Not just a team — our team. It’s insane.”

Soccer was their first love; their father, who died in 2017, briefly played professionally. Their foundation, the Charles Antetokounmpo Family Foundation, seeks to help disadvantaged people in Greece, the United States and Nigeria, where their parents grew up.

‘Protect the family.’

The idea that someone with Giannis’s salary would worry about money might strain credulity, but he is thrifty — cheap, he’ll admit.

“I need my kids to spend my money,” he said, smiling.

He said he wants six children, and is almost halfway there. He and his fiancée, Mariah Riddlesprigger, have two sons, Liam and Maverick, and Riddlesprigger is pregnant with their third child, a girl.

Antetokounmpo gets concerned when his children are pulled into the spotlight with him. In the United States, his fame is perhaps not as overwhelming as it would be were he playing in a bigger city. But in Greece things are different.

“The way LeBron James is or Michael Jordan is for the States, the same way I am for Greece,” he said. “Maybe larger.”

He has noticed people filming his children in their stroller and at a birthday party. He wants his children to be able to decide whether they want to live lives in the public. On social media, he typically covers their faces.

When he thinks about growing his wealth, he is thinking about his children’s futures, too.

The brothers try to make business decisions as a group, often on a messaging thread titled “Antetokounbros” (which is also the name of a store they have in Athens; they’re opening one in Milwaukee soon). They save personal texts for a different thread titled “F.O.E.,” which stands for family over everything.

He said he has felt taken advantage of in the past by some of the people hired to handle his life, money or off-court interests, and was confident that will never happen with his family.

“I see it with my teammates, some of my teammates,” Antetokounmpo said. “‘Oh, my cousin did this. My mom did this.’ You see it. It’s public. Moms arguing with their sons, suing one another for property that doesn’t belong to them. You see it every day.”

He added: “The way we were raised in Greece and the things that we went through every single day to provide for our family, all those moments brought us close. They knew that at all costs I would protect the family, take care of my brothers. And I did.”