The Matches that Made Serena the GOAT: Williams d. Martina Hingis, 1999 US Open final

Tennis Honors: Naomi Osaka on Serena Williams

This week, Steve Tignor looks back at five contests that made Serena Williams the greatest of all time.

Someone was telling me, ‘The president of the United States wants to talk.’ I was thinking, ‘Wow.’

Serena has said that if there’s a defining moment to her career, one that set the tone for the way she would play, it came in the 1999 US Open final, when she was 17. She had won the first set over Martina Hingis, but had squandered a chance to serve out the match, and win her first major title, in the second set. Now she found herself in a tiebreaker, with a look at a second serve. Serena asked herself: Should I attack? Should I play it safe?

You probably know what happened next: She went for broke, hit a forehand return winner, and won the Open. She trusted her shots that day, and didn’t stop trusting them for the next 23 years.

“I was really mentally tough out there,” she said afterward. “I wouldn’t give in to anything. There comes a time when you have to stop caving.”

Winning the US Open was Serena’s original dream. “I didn’t think past that,” she wrote in her retirement essay for Vogue in August. “And then I just kept winning.”

And kept passing Hall of Famers on her way to the top of the historical heap. Serena began that process by beating the 18-year-old Hingis, who had already won five Slams. Tennis fans thought it was the start of a long rivalry, but Hingis wouldn’t win another major. Looking back at this final, you can see rise of Serena and the demise of Hingis begin in the opening games.

The Swiss was No. 1, but she was discovering that there was a stronger, better player on the other side of the net. Tennis’ 21st century—Serena’s century—was about to begin.

There was another player in the stadium that day who Serena was in the process of moving past—her sister. Venus, who lost to Hingis in a close semifinal, watched the final from underneath a black hood. Venus had been the star of the family, but it was Serena who won their first major. Yet her support for her little sister never flagged.

“I saw Venus over there really making sure, pumping me up,” Serena said. “It really helped me.”

A few minutes after the match, another supporter was on the line: President Bill Clinton.

“Someone was telling me, ‘The president of the United States wants to talk.’ I was thinking, ‘Wow.’”

Serena had her first taste of major success, and life as a celebrity. She seemed to like both.