“I Love Reinventing Myself”: From Federer’s Challenger to Milei’s Political Lion, Diego Hartfield’s Journey

8 min read
May 14, 2025, 7:00 PM
Diego Hartfield plays against Roger Federer on day two of the Australian Open 2008

Diego Hartfield plays against Roger Federer on day two of the Australian Open 2008 (Photo by Mark Dadswell/Getty Images)

BUENOS AIRES – One life can hold many lives. You can shake hands with Roger Federer on the tennis court and, years later, throw yourself into the arms of Javier Milei. Argentine Diego Hartfield knows this well. He was first a tennis player, then a financial broker, and now he wants to reach the heights of politics.

“I did very well in the financial markets, and I am convinced that I will end up playing a leading role in politics. I can’t rank myself, but I will do so with the same conviction I had when I played tennis,” Hartfield, who reached number 73 in the world rankings more than 15 years ago, told RG and CLAY.

Nineteen years ago, he reached one of the peaks of his career, challenging Federer on centre court at Roland Garros, and two years later he did the same at the Australian Open. In neither match did he manage to take a set off the Swiss, who was in the prime of his career, although he did take him to a tiebreak in two sets in Paris.

“I love reinventing myself. I retired from tennis quite young, and at 30 I wanted to do something new in my life,” explained Hartfield, who is fascinated by the decisions being made by the ultra-liberal libertarian Milei, president of Argentina since December 2023 and an ally of Donald Trump and Elon Musk on the international stage.

“I became a stockbroker. I open accounts for individuals and companies on the stock market, but now I really like what this new government is doing.”

Hartfield, a tall blond man of German descent, lives in Oberá, in the northern Argentine province of Misiones, famous for a stunning tourist attraction, the Iguazú Falls. La Libertad Avanza (LLA – Freedom Advances), Milei’s party, became interested in him after an interview published in 2024 in CLAY, in which he enthusiastically praised the government and theorised about economics and finance.

Embracing Politics with Passion

One of the things Hartfield insists on is that he never really liked tennis very much. Politics, on the other hand, seems to fascinate him, and his launch as a candidate in Misiones was impressive, metamorphosed into the lion that is the symbol of Mileism.

Hartfield, 44, reached number 73 in the world rankings in 2007, 2009, and 2010, although in those years there were so many talented Argentine players that he was unable to fulfil his dream of playing in the Davis Cup.

In 2006, the draw pitted him against Roger Federer in the first round of Roland Garros, a momentous occasion for a player who did not feel talented and for whom everything came with great effort.

“You tend to normalise things when you’re there, you know? You tend to believe that what’s happening to you is normal. Then you reach the top 100 and, well, you’ve worked your whole life to get there, and everything is so progressive that it’s hard to say, ‘Wow, look where I am!’”

“Maybe now it’s easier to say, ‘Wow, look where I’ve been.’ Although you never stop comparing yourself, because at my peak I was number 8 in the country and at that time there were 13 of us in the top 100. I wasn’t even close to playing in the Davis Cup. But today, am I number eight in the world of finance in Argentina? No, no, not even close.”

Being number eight in Argentine politics also seems a long way off, but at the start of his third life—the first was tennis and the second finance—Hartfield feels capable of anything.

“We’re up 2-0 in the first set. I started off on the right foot, starting with a break. With all this strength they’ve given me, I feel very emboldened. I want to travel around the province and talk to each of the Missionaries so that together we can have a rich province that works and grows without the burden of the state. I feel very comfortable with the ideas of La Libertad Avanza.”

A Journey Shaped by Economic Crisis

Tennis is an important issue for the men who run Argentina’s economy today. Luis Caputo, Minister of Economy, plays, and Pablo Quirno, Secretary of Finance, plays at a very high level. A few days ago, Caputo invited Hartfield to his home to talk about politics, economics, and finance—and tennis, of course. He also met the President.

“Those two interviews in which I talked about tennis and my political ideas definitely had a very strong impact on my private life and my image here in Misiones. I am entering politics because, in reality, all the ideas that this government has been promoting since it took office are ones that I myself have been advocating for years. When Milei took office and appointed Caputo as minister, I regained my hope that we could once again be a normal country. When they called me, I felt privileged and very excited to be part of this project, and I did so with total conviction.”

“I am in close contact with President Milei’s economic and political team, and the support for me in Misiones is total. The path ahead is the same as the one taken at the national level. We are going to replicate in the province the same work that was done to deregulate the economy and lift the province out of poverty.”

Milei is the first economist to become president of Argentina. He is an ultra-liberal libertarian who leaves no one indifferent, who ignites passions: many adore him and many others detest him.

“I am very optimistic, very. If I had chosen a way to do things today, it would be this way.

I have always said so. You have to be a very strong communicator with a high level of popular conviction, someone who is capable of putting the knife in for surgery and having the people accept it.”

Hartfield recalls an important reason that led him to become a professional tennis player: the Argentine economic collapse of 2001/02.

“We were a struggling middle-class family in the 2001 crisis. And I honestly saw tennis as a chance to earn money, to have a career. I liked that idea and put all my energy into it. Now… what would have happened if I had studied economics instead of becoming a tennis player? Today, with 20 years in the profession, it would be a different story. We don’t know.”

“I’m not a very technical guy. But hey… when I played tennis, I wasn’t a very technical guy either. I tried to be more on the side of common sense and perception.”

Tennis wasn’t his passion, but he’s grateful to the racket.

“I have very fond memories. I don’t have any great friends. Yes, I have very good acquaintances and good contacts. At the time, there were a lot of us players and we were very supportive of each other on the road. You could have disagreements like with anyone, but we faced each other many times on the court as friends. And many times we even had to warm up with the person you were going to play next.”

“Sharing a hotel in times of poverty or, shall we say, not wealth. We learned from the bottom up, we valued every match. I have great memories of my time as a tennis player.”

Sebastián Fest
Sebastián Fest
Tennis Reporter

Journalist. Founder of CLAY, a global tennis media platform. More than 70 Grand Slams covered during a 35-year journalistic career. He is the former Sports Editor of the German news agency DPA and the Argentine newspaper La Nación. He has reported on every FIFA World Cup since 1998 and every Olympic Games since 1996.

He is the author of 'Ni rey ni dios' and 'Messiánico', biographies of Lionel Messi, and 'Sin red', a decade-long journey following Roger Federer and Rafael Nadal, as well as 'Gracias', a biography of Nadal.

Correspondent for Spanish newspaper El Mundo in South America, he co-chaired the International Tennis Writers Association (ITWA), an organization that gathers the 100 most influential tennis journalists in the world, and is currently a board member. He was also Editor-in-Chief of Around the Rings, a site focused on high-level sports politics.

Interests:
Tennis
Olympic Sports
Politics
Music
Travel
Books

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