)[4] At age 13, Shortz wrote to Language on Vacation author Dmitri Borgmann for advice on how to pursue a career in puzzles.

[10] He also earned a Juris Doctor degree from the University of Virginia School of Law (1977), but did not sit for the bar exam and began a career in puzzles instead.

[13] A few months later he became the crossword puzzle editor for The New York Times, the fourth in the paper's history, following Eugene Thomas Maleska.

The lucky player is picked randomly from a group of submissions containing the correct answer to a qualifier puzzle issued the week before.

[20] In 2017, Shortz published a Times crossword by a prisoner named Lonnie Burton who was convicted of raping a 15-year-old boy, in addition to having burglary and robbery charges, prompting backlash from some solvers.

[...] I understand Shortz’ reflex to hold back such dark information given the levity of a puzzle, but not doing so may have made matters worse.

"[22] At various times in his career Shortz has apologized for cluing decisions that sparked public backlash for being racist, sexist or offensive.

[23][24] In 2019, The New York Times issued an apology after Shortz chose to publish the racial slur "BEANER" in the crossword, cluing it as "Pitch to the head, informally".

Shortz defended his use of "BEANER" and noted he has published and stands by the benign meanings of the terms "CHINK" and "GO OK" (or "GOOK"), both slurs for people of Asian descent.

[50] In his free time, Shortz also enjoys biking, reading, traveling, and collecting antique puzzle books.

[55][56][57][58] During Shortz's hospitalization and initial recovery, Joel Fagliano oversaw editing of the crossword for The New York Times through December 2024.