The Puzzle Of Alan Southworth

Westporters have a special relationship with the New York Times crossword puzzle.

Every year, puzzle editor Will Shortz hosts a competition at the library. (The upcoming 19th annual event is February 3.)

When library director Maxine Bleiweis retired in 2015, Shortz showed up — and presented her with a specially created, “MB”-themed puzzle.

Two months ago, “Westport” was even the answer to a clue — “Affluent Connecticut town” — in a Times crossword puzzle.

But our special relationship goes only so far. To be published by the paper, a puzzle must be good. Very good.

Alan Southworth’s is. Which is why — ta-da! — the 2010 Staples High School graduate makes his debut today as a New York Times puzzle constructor.

Alan Southworth (left) and Will Shortz, at last year’s Westport Library crossword puzzle contest.

The best constructors know a lot, about a lot of things. They have varied interests. Southworth definitely does.

At Staples he sang with the Orphenians, joined the jazz band, competed on the math team, and played freshman basketball.

At Princeton he majored in geosciences (and was certified in sustainable energy and environmental studies). He works now as an energy market consultant, in a Manhattan firm run by 2001 Staples grads Gabe Phillips and Jonathan Spivak. In his spare time, he plays singer-songwriter gigs around the city.

Southworth always loved words. He grew up playing Scrabble and Boggle with his mom, and relaxed before bed with Sudoku and KenKen.

In college, he discovered crosswords. He and his friends challenged themselves with the Times puzzle in the dining hall.

After graduation, he commuted nearly 2 hours each way. Vowing to be as productive as possible, he spent his train rides writing song lyrics. That soon morphed into crossword theme ideas.

His college friend Ryan McCarty had a couple of puzzles accepted by the Times. He wanted to collaborate. So Southworth devised themes. McCarty did most of the grid construction. Together they wrote clues.

They’ve kept a Google Doc of puzzle ideas ever since.

Their first 2 puzzles were rejected. This one was accepted, Southworth thinks, because the theme answers were a  bit “cleaner,” and the grid more open (fewer black squares in the middle).

Having a crossword accepted is quite an accomplishment. Having your first one run on a Thursday is remarkable. That’s the toughest day for a themed puzzle. (Monday is the easiest; Tuesday and Wednesday are a bit harder. Friday and Saturday are reserved for themeless — but more difficult — puzzles.)

Southworth has a digital subscription to the Times. But today he’ll buy a dead-tree copy of the paper — and make copies for his co-workers.

Here in Westport, his parents have promised to save their copy for him too.