Highfliers in the Crossword Underground

Sam Trabucco ’11
John Lieb
Andrew Kingsley ’12

Sam Trabucco ’11 was the focus of the New York TimesApril Wordplay feature, “Who Made My Puzzle.” This millennial has already published ten puzzles in the NYT.


Sam is a protégé of crossword maestro David Quarfoot, who taught for a few key years at Roxbury Latin and in that short time planted a hardy seed for future RL puzzle makers. Sam calls his first puzzle—published in Tripod, RL’s student paper—“terrible…a one-off, fun project I might have forgotten about a few weeks later if not for the auspicious introduction of David Quarfoot to my high school’s math department my senior year.” Mr. Quarfoot encouraged Sam to start writing crosswords seriously, directing him to the best puzzle-making software and quality word lists and offering lots of advice.


Sam, a 2015 MIT graduate with degrees in math and computer science, always enjoyed puzzles as a child, especially Scrabble and word games in general. “Paper puzzling” began in earnest for him after he attended his first MIT Mystery Hunt as a high school junior; after that he started solving crosswords regularly. As for their creation, he finds grid construction “a fun and satisfying problem to solve, and theme development/clever cluing to be nice creative outlets.” He also enjoys sharing his puzzles with friends, watching them solve them, and hearing their feedback.


In addition to Sam, Mr. Quarfoot’s RL disciples include Math Department chair John Lieb and then-student Andrew Kingsley ’12 (now a member of the English faculty), both of whom have since had numerous puzzles published in the NYT. Mr. Lieb first revealed his wordplay avocation in 2012 when he teamed up with Mr. Quarfoot to produce an RL-themed crossword for The Newsletter. He had only been constructing them for two years when his first puzzle appeared in the NYT in 2013.


Most recently, Messrs. Lieb and Kingsley collaborated on a puzzle that appeared on Saturday, 28 April. They enjoy their shared interest. “As a duo, we find we work nicely together,” says Mr. Kingsley, “especially since we can pop into each other’s office during free periods and talk shop.” Last summer, they teamed up to create a crossword tournament—Boswords— at Roxbury Latin. The first-of-its-kind event attracted 149 competitors from all over New England. (Mr. Quarfoot provided a challenging championship puzzle for the top three competitors.)


Who knew back in 1645 that John Eliot’s “little nursery” would also become—370-odd years later—a little incubator of master crossword makers?