Hilton Wexler is a professional chess player and friend of Benny Watts. He makes his first appearance in Benny Watt's apartment in New York, and meets Beth Harmon, the U.S. Champion at the time. He asks Beth Harmon if she ever does chess puzzles and problems. She replies and says that she found problems as "irrelevant", stating that they are positions that never come up in real games. Hilton then challenges her to a problem in which she completes in seconds, much to Hilton's surprise. Benny then escorts Hilton away from Beth.
Throughout the episode Hilton challenges Beth to a simultaneous, meaning Beth will play Benny, Hilton, and Arthur at once. Beth repeatedly defeats all three of them under time limit.