In 1995, Serena turned pro. Two years later, she was already No. 99 in the world rankings—up from 304 just 12 months before. A year later, she graduated high school, and almost immediately inked a $12 million shoe deal with Puma. In 1999, she beat out her sister in their race to the family’s first Grand Slam win, when she captured the U.S. Open title.