On a court named for the last Black American man to win it, Ben Shelton stepped into history Friday night — defeating compatriot Frances Tiafoe in the first Grand Slam semifinal ever contested between two Black men. The 23-year-old Floridian, shaped by near-misses and late-night battles, now stands one match away from ending a 23-year silence in American men's tennis. On Sunday at the U.S. Open, he faces Alexander Zverev — and the longer arc of a sport that has waited a generation for this moment.