Crossing Words with Stu Ockman

Puzzlemaker Stu Ockman of Rose Valley created this crossword with coldblooded precision.

Puzzlemaker Stu Ockman of Rose Valley created this crossword with coldblooded precision.

Their phone call was about finished when Stu Ockman’s college friend Adam Perl mentioned that he was going to have a crossword puzzle in the New York Times that Thursday. “Even though I’d been doing them since I was a teenager, I never knew they were contributed by individuals,” Stu said. “Adam and I are competitive, and that’s all it took to get me interested.”

Stu found Crossword Compiler software online and sat down at the electronic drawing board in his Rose Valley home. Before the free trial period ended, he had submitted a few puzzles to the Times. “I got rejections from Will’s assistant, Paula Gamache, saying ‘Will says thanks, but must send regrets on your [latest puzzle] whose theme didn’t excite him enough. Sorry about that. He did appreciate seeing this, tho.’ [Will, of course, is Will Shortz, the puzzle editor of the Times and the face of crosswords.]

Further encouragement soon came in an e-mail from Will Shortz himself, also rejecting a puzzle, but providing Stu with reasons why (e.g. “the entry TEA GUEST sounds made-up”).

“I bought the software and really made a good start,” Stu said. “Of the first 60 or so puzzles I submitted, Will accepted eight,” though a dry spell soon followed. He was hooked, and though he hasn’t quit his day job — he is an engineering consultant and an expert witness in construction disputes, internationally — he makes puzzles much more efficiently with the benefit of experience.

“The first puzzles took me 12 hours, 24 hours, or more. But then you figure out the process, the software, the dictionaries; so now in a basic puzzle, I can fill the grid in about 30 minutes,” Stu said.

“A puzzle starts with the theme, and the size grid you want to fill — 15 x 15 grids for Times daily puzzles and 21 x 21 for Sunday. If you think it’s a brilliant idea, and you have some great theme entries, you invest the time and go for a Sunday puzzle.”

As theme words are entered into the grid, the software suggests words for a particular configuration of intersecting letters. Then comes clueing. Stu said: “Choosing words for the grid is the thing that takes the longest to learn. A single word can be a puzzle killer, but having the right words can really get Will excited.” He reads a short Shortz e-mail from last September that says “Got it. Thanks Stu. Very happy to have this gorgeous puzzle.” That gorgeous puzzle has yet to be published, but will probably be a Saturday crossword. Saturday, as Times puzzle solvers know, is the hardest puzzle of the week, which starts easily on a Monday. (The Sunday puzzle is sui generis; it’s the only one that has a title, with difficulty about on a Thursday level, but twice as big.)

The New York Times is not the only game in town — the Los Angeles Times and the Jerusalem Post have also published puzzles he’s developed as posthumous tributes to Harold Ramis and Neil Simon — but it’s Stu’s primary market. “The rest I’m saving for my self-published crossword book.”

Pickup an issue of this week’s Swarthmorean! The puzzle is on page 8.

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