At the Waldorf Astoria, she caught glimpses of Donald J. Trump, Bill and Hillary Clinton and Barack Obama.

That’s to name just a few of the politicians Regina Gatewood spotted in her 16 years as a banquet waitress at the Waldorf, on Park Avenue in Manhattan.

One time, Phillip C. McGraw, better known as Dr. Phil, asked her for directions to the restroom. “I feel like I know you,” she recalled telling him. “And he said, ‘You do know me.’”

Ms. Gatewood has come far since her mid-30s, when she entered New York City’s shelter system with her two sons after their father left. She worked long hours as a waitress and in temporary jobs until she could afford public housing, and eventually her own home on Staten Island. She started at the Waldorf in 2000 and worked her way up, becoming a full-time employee in 2010.