How Venus and Serena Williams' first endorsement deals proved to be game-changing

Venus Williams made headlines across the globe as a 15-year-old after signing a record eight-figure deal with Reebok. She had been on the Tour a few years, having enjoyed some big results. But it was this mega-deal in 1995 that announced her arrival long before any of her Grand Slam triumphs.

Williams' younger sister Serena would soon follow suit, signing her first endorsement with Puma in 1997.

While both women have gone on to sign much more lucrative deals over the course of their illustrious careers, these initial endorsements tell the endearing story of big sports brands taking a chance on two undeniably talented, if somewhat inexperienced, young female athletes.

How Venus and Serena Williams got big sports brands to back them

Venus Williams signed an eight-figure deal with Reebok in 1995.

Venus' 1995 deal with Reebok stands out for being the first-of-its-kind for a female tennis player.

The American, who was ranked No. 3 in the world at the time was on an upward trajectory, and awarding her with a $12 million deal made sense.

By offering a lucrative deal to an African-American in a sport dominated by white athletes, Reebok managed to capture the imagination of a whole new demographic. Venus' bold and unconventional outfits - which included denims and overalls - not only made her an instant icon, they also put Reebok on the map.

Serena, for her part, went even further by taking an active interest in the design process of her on-court outfits. Designers at Puma, including Amy Denet Deal, recalled a 17-year-old Serena Williams bringing them sketches of ideas for outfits to creative meetings in a recent feature for 'The Undefeated'.

“I just thought that was the coolest thing ever that this young woman showed up with a bunch of sketches,” Deal said. “You’re talking about someone who was 17 and had no training in design. She wanted to be the most powerful player. But this effortless sense of style that she’s developed over all these years — that was in her heart.”

Serena (L) followed in sister Venus' footsteps fairly naturally.

This was shortly after Serena had signed up with Puma after a marathon 12-hour-long negotiation meeting in 1997. The deal, much like Venus' 1995 contract with Reebok, was brokered by the man who introduced them to the sport; their father Richard.

Antonio Bertone, who worked as a brand manager for Puma at the time, recalled meeting Serena and her father in the company's LA office. He conceded that executives at Puma saw in the Williams sisters the potential "to change the sport".

"Arnon [Michlan, Regency Enterprises, founder of Puma's major stakeholder Regency Enterprises] recognized Serena and Venus’ ability to change the sport of tennis,” Bertone said. “…like, ‘We’re totally getting back into tennis with Serena.’”

Serena paired her iconic 2002 US Open Puma catsuit with a pink headband.

Bertone, however, also remembered the excurciatingly lengthy process they went through to arrive at the final deal, even recalling Richard Williams shrewdly "buying time" to see how far Puma was willing to go.

“I was convinced he wasn’t even talking to her,” Bertone said of Richard Williams' multiple phone calls to wife Orceane over the course of the meeting. “That he was just buying time, drawing things out to see where we’d end up.”

Bertone said signing Serena Williams, who famously dozed off while in the midst of negotiations, was a deal that Puma wasn't willing to pass on. And in the 23-time Grand Slam winners' own words, things worked out well for both parties.

“I wanted a sponsor. I wanted someone to believe in me,” Williams wrote about her deal with Puma. “It wasn’t just Puma taking a chance on me. It was me taking a chance on Puma. It cut both ways.”

Venus and Serena Williams sign $40 million deals to solidify their status at the top

The Williams sisters continued to push boundaries with their path-breaking careers.

Serena Williams was the first of the sisters to lift a Grand Slam title. She took home the 1999 US Open crown and a hefty $750,000 check, with sister Venus following suit at the 2000 Wimbledon Championships.

It was no surprise then that when their endorsement deals expired in 2000, both signed even more lucrative contracts. Venus continued her association with Reebok, signing a five-year contract worth $40 million.

Serena meanwhile, got her own $40 million five-year deal with Nike. The identical deals, signed at the turn of the century, once again solidified the duo's status at the top of the women's game.

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