Before super-agent Max Eisenbud joined Li Na's team, tennis players sponsored by Nike had to follow one strict clothing rule upon signing:

“When you sign with Nike, one of their big things is no patches,” Andy Roddick recalled on the lastest episode of his new podcast, *Served with Andy Roddick*. “There’s the (Maria) Sharapovas and there's the (Rafael) Nadals, and there's guys like me... We like to add stuff to supplement the fact that we can't hit a backhand."

Today, players are seen with logos up and down their sleeves and tops without a second thought—even the Swoosh's ambassadors—and it's all thanks to Li asking Eisenbud to "make more money" for her.

“My tombstone will probably say that I was the first agent to get Nike to allow patches,” Eisenbud told Roddick.

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The Mercedes patch was one of the first ever sewn onto Nike tennis attire—without incurring a massive fine.

The Mercedes patch was one of the first ever sewn onto Nike tennis attire—without incurring a massive fine.

Eisenbud and IMG signed on with a Li that was just breaking into the Top 40—and right after she had renegotiated her contract with the Chinese government to keep 80 percent of her earnings and was looking to make money fast. The first thing he did was review her current contracts, and the one with Nike stood out for being the “wrong number”: $50,000.

“At the time, all these Chinese brands were coming in. I found out that there was a Chinese brand that wanted to pay her $1.2 million,” Eisenbud said. “I go to meet her and tell her the great news, and she says to me I want to stay with Nike.”

After recovering from Li's surprising response, Eisenbud returned to Nike at face value—except the Swoosh said there’s "no way" they’re paying her that much.

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“This is what we're going to do,” Eisenbud famously told Nike. “You're going to pay me half, and you're going to give me patches. It's going to be China, so you're going to be able to justify to the world, to the Sharapovas and (Roger) Federers, that you're only doing patches in China.”

“They said, deal. And I called our lawyers to make sure this contract gets signed in 24 hours.”

The rest is tennis fashion history. Nowadays, players signed with Nike are no longer restrained by patch restrictions. If anything, it's tournament-specific regulations that tend to get in the way of a fashionable sponsorship, like Wimbledon's logo size and color rules. At the Australian Open this year, for example, Marton Fucsovics—who wears Hydrogen—was forced to change shirts for failing to comply with logo restrictions.

Li's impact: Naomi Osaka wears various sponsor patches on her Nike dress.

Li's impact: Naomi Osaka wears various sponsor patches on her Nike dress. 

But Li’s fashion-movement of a deal with Nike didn't mean her money-making journey was a simple one. Roddick and Eisenbud's discussion continued onto how she was able to negotiate a new agreement with the Chinese government, as well as a six-month period where she wasn’t speaking to Eisenbud.

In the same hour and a half episode, the agent also revealed that golf superstar Tiger Woods was the inspiration behind Sharapova's lucrative brand partnership strategy—i.e. the strategy that made Sharapova so rich that Li wanted Eisenbud to represent her, and the reason why current players like Emma Raducanu continue to flock to Eisenbud and IMG.

Roddick and Eisenbud's chat is currently live on YouTube along with all four previous episodes. Starting this Sunday night, March 3, Served with Andy Roddick will be aired on T2, Tennis Channel’s second network.