Inside the Elite, Underpaid, and Weird World of Crossword Writers

For would-be constructors without such personal connections, there’s the Crossword Puzzle Collaboration Directory. The Facebook group launched in 2018 with an associated Google form that pairs newcomers with mentors. It has always been explicit about its aims to provide resources to underrepresented groups: “This matching form is intended specifically for [women, people of color, LGBTQIA+ people, and disabled people] as a tool for addressing structural inequities in the crossword industry. Because our mentors’ time is finite, if you’re not a member of any such group, we ask that you refrain from using the form.”

The explicit intentions aren’t enough, though, and in fact at times the group has served the opposite purpose. When professional opera singer Daniel Okulitch, a white man, was inspired to try his hand at crossword construction after he first started regularly solving them during the pandemic, he found his way to the group. In response to a question he posted, Okulitch was contacted by Brad Wilber, a longtime constructor (60 Times puzzles since 2005) and an opera fanatic. A fan of Okulitch’s singing, Wilber offered his services as a mentor. Okulitch has now published three Times puzzles, including two with solo bylines.

Such stories are indicative of the Facebook group’s ambivalent impact, says Erik Agard, the crossword editor of USA Today and one of the directory’s co-founders. On the one hand, he says, “I’ve seen a lot of people who have participated in it go on to have puzzles in a variety of places and shout it out, which is exciting and gratifying. I personally have made connections to great newer constructors through there.”

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