Did Anna Wintour's Fashion Connections Help Roger Federer Ditch Nike for a $300M Uniqlo Fortune? Here's the Truth

Sport and fashion enthusiasts must remember that for years, Roger Federer was synonymous with Nike. The swoosh across his headband became part of his identity as familiar as his one-handed backhand or his calm presence on court.

So when the Swiss maestro swapped Nike for Uniqlo in 2018, eyebrows rose across both the tennis and fashion worlds. What wasn't known until recently is how a quiet breakfast with Vogue's Anna Wintour, a longtime friend and fashion confidante, helped him land a deal worth $300 million. And the twist? Federer never actually walked away from Nike; they walked away from him.

Nike Walks Away from a Legend

Speaking on Andy Roddick's Served podcast, Federer's agent and close friend Tony Godsick revealed the true story behind the split. 'He didn't leave Nike. Nike left him,' Godsick said. 'We were trying to re-sign, and they chose not to. He would have stayed.'

By early 2018, Federer's 10-year contract with Nike, signed in 2008, was coming to an end. Despite his long association with the brand, the renewal never materialised. 'I spent a whole year trying to get it done,' Godsick recalled. 'At that point, Roger was 36. Most players are retired by then, and Nike couldn't decide how to value someone who'd already done everything.'

The timing seemed cruel. Federer had endured a four-year Grand Slam drought but stormed back to win the Australian Open and Wimbledon in 2017. Even that resurgence didn't change Nike's stance. 'He gave me all the goods,' Godsick said, 'but I still couldn't get it done.' When the contract expired in February 2018, Godsick left Nike's Oregon campus empty-handed.

From Setback to Strategy

The failed renewal was a blow for both Federer and his team. 'I remember thinking, I can't believe this,' Godsick said. 'I was going to go down as the agent who couldn't renew the greatest player of all time.'

With Nike out of the picture, Godsick tested the market. The response was lukewarm. 'Everyone said no,' he explained. 'One brand told me, 'He's already branded with Nike – we're not interested.' Another said, 'We'll have to wait until next year.'

Federer's clean-cut image and fashion sensibility had long set him apart from his peers. Still, few brands were ready to bet on a 36-year-old player nearing retirement. Then came an unexpected lifeline, not from the sports industry, but from the fashion world.

Anna Wintour's Well-Timed Favour

Federer's friendship with Vogue's former editor-in-chief Anna Wintour stretched back nearly two decades. 'I didn't know who she was at first,' Federer told Us Weekly in 2024. 'She's a massive tennis fan. She even skipped fashion shows to come watch my matches at the US Open.'

Wintour had long been a sounding board for Federer, offering advice that extended beyond fashion. So when Godsick hit a wall, he turned to her. 'I was having breakfast with Anna in New York and said, 'I need a favour. Do you know Mr Yanai?' he recalled, referring to Tadashi Yanai, the billionaire founder of Uniqlo's parent company, Fast Retailing.

'She said, "I know him," and sent a note. Twelve hours later, I had a message from his assistant saying Mr Yanai would meet me in Japan.'

That meeting proved transformative. 'I told him we weren't there to use him as leverage against Nike,' Godsick said. 'We wanted to build something long-term, something that went beyond tennis.' Yanai agreed. Within months, Federer signed a 10-year deal with Uniqlo, reportedly worth $300 million with no performance or appearance clauses attached.

As for Wintour, her influence once again proved decisive. For decades, she shaped global fashion; in this case, she helped shape one of sport's most unexpected financial victories.