Nearly 1,300 people spent this past weekend racing to fill little boxes inside larger boxes, ever mindful of spelling, trivia, wordplay, and a ticking clock. They were competitors—newcomers, ardent hobbyists, and elite speed solvers—in the American Crossword Puzzle Tournament, the pastime’s most prestigious competition. And most of them got creamed by some software. The annual event, normally set in a packed hotel ballroom with solvers separated by yellow dividers, was virtual this year, pencils swapped for keyboards. After millions of little boxes had been filled, a computer program topped the leaderboard for the first time. Advertisement Dr. Fill is the algorithmic creation of Matt Ginsberg, an Oxford-trained astrophysicist—and computer scientist, stunt pilot, bridge player, novelist, and magician—who lives in Oregon. When he began the project a decade ago, his motivation was simple: “I sucked at crosswords, and it just pissed me off.” Ginsberg hoped one day to walk into the tournament hall, wave his laptop above his head, and show the humans who’s boss. Now, if only virtually, he has.