When Jon Stewart prepared to propose to his girlfriend in the 1990s, the comedian and former “Daily Show” host contacted New York Times Crossword Puzzle Editor Will Shortz to ask for help creating a personalized puzzle to pop the question.
Shortz says he knew a better person for the job: He turned it over to Fred Piscop of Bellmore.
Piscop, 66, is USA Today’s crossword puzzle editor and a past crosswords editor for The Washington Post Magazine, as well as a frequent crossword puzzle constructor for Newsday and The New York Times. He’s also specialized in commissioned puzzles for special occasions.
Stewart’s people say he’s not doing interviews, but Shortz says the entertainer told him the puzzle was framed and hangs in his home.
Today, Piscop is marking his own milestone with his 1,000th crossword puzzle in Newsday. Piscop’s first puzzle for this newspaper appeared in 1992, and the theme was The Three Stooges — one of Piscop’s beloved acts.
“I’m fascinated by wordplay, really mind-stimulating stuff,” Piscop says.
Piscop’s shoulder-length white hair makes him look like a member of a rock band; he’s also got a close-cropped mustache and beard, and on a warm August evening, he was wearing a “Black Oak Arkansas” T-shirt depicting one of his favorite 1970s groups. Piscop is an Ivy League grad who eventually eschewed the corporate world and lives in a one-bedroom apartment.
College at 16
Piscop grew up in East Meadow. He was part of an experimental, accelerated program that combined fourth through sixth grades in two years, and he credits his teacher, George Bredehorn, with introducing him to word games.
Piscop started his freshman year at Cornell University in Ithaca at age 16, studying industrial engineering. After college, he spent one year playing the keyboards with a band called Royal Society before trying the corporate route.
“I got a job at Fairchild Republic,” Piscop says. “I hated every minute of it. It was just boring, boring. I stayed one year.”
After earning an MBA from C.W. Post, Piscop went to work for Doubleday in Garden City as a project engineer. In 1980 or so, he bought a used Apple computer, taught himself programming and moved into data processing for various companies on Long Island.
For decades he also played the keyboards in the Wes Houston band. Along the way he was married and divorced twice. He also owned two homes, which he says he disliked: “There was too much to do — chores, mowing the lawn, just nonsense like that.”
Scrabble? No thanks
Piscop kept in touch with Bredehorn, forming a group that met every Tuesday night for more than 30 years to play word games at the teacher’s Wantagh home. Bredehorn died in 2012, but his wife, Dorothy, still welcomes the group when it meets.
Crossword puzzle creator Stan Newman, who became Newsday’s crossword puzzle editor in 1988, says Piscop cold-called him and invited him to join the weekly word games at Bredehorn’s house. “Having seen Alfred Hitchcock movies, I thought there was a certain possibility I’d be welcomed in and then the kitchen cleavers would be drawn,” Newman jokes. Newman, who lives in Amityville, is still part of the group.
Piscop likes word games, but that doesn’t mean he’ll play any old word game. “I haven’t played Scrabble in 40 years,” he says. “There’s a whole different mindset to Scrabble.” First, knowing obscure words is helpful in Scrabble, he says, while they aren’t great for crossword puzzle clues. And, a great crossword puzzle word might be an invalid Scrabble word if it involves a proper name, he says.
Piscop started submitting puzzles to Newman, and also to other outlets while he was still working a day job, indulging in his love for words and word play. “I just felt like trying it,” he says about constructing crosswords. His first puzzle was published in Crossw-rd magazine in 1990; in the beginning he created puzzles using pencil and paper.
Then, in 1995, at the age of 45, he was laid off.
“By that year I had totally had it with corporate America. I said, ‘To hell with this, I’m not going back to 9 to 5,’ ” Piscop says.
Piscop has been providing Newsday with three to four crossword puzzles a month for decades, editor Newman says. The process has advanced with the development of computer programs; Piscop now uses Crossword Compiler for Windows. “It checks for symmetry, duplicated words,” he says. “You can link databases. If you have a few letters missing you can search for words that fit that pattern.”
Here’s how Piscop constructs a puzzle, typically working at a cluttered computer desk in his tiny apartment: First, he lays in the major theme words or phrases. For his Three Stooges puzzle, for instance, his answers were word plays that included the Stooges’ names: EdgarAllenMoe, HelenCurlyBrown and JohnLarryMore.
Then he sets up the rest of the diagram, placing the blackened squares. One rule in creating a crossword is that the grid must look the same upside down as it does right side up, to create symmetry aesthetically pleasing to the solver.
After that, Piscop fills in the other words: no more than 78 entrants across and down for a Newsday daily puzzle; Sunday allows up to 146 clues. Other basics include no two-letter words, and every letter has to appear in two words, both across and down, to give solvers two chances at every box.
Piscop uses online dictionaries and encyclopedias to form his own word lists. “He’s rated words according to desirability,” says The Times’ Shortz, for whom Piscop constructs a monthly online bonus puzzle for the paper’s subscribers. “If the subject is horses, he’ll go through his database and find every answer to do with horses.”
Piscop says it takes him an hour to two hours to complete a puzzle for which he might earn between $50 and $1,000. (Newsday pays $55 for a daily puzzle and $225 on Sundays, Newman says.) “Making a diagram is just like solving a puzzle,” Piscop says. “You’ve got to get everything to fit. You’ve got to do it with interesting vocabulary.”
Despite providing daily entertainment for thousands of readers who love to test themselves, crossword constructors “toil in relative obscurity,” says Newman, who still creates puzzles for publication. “I don’t get stopped on the street. I don’t get asked for an autograph.”
Still, Piscop says one of his claims to fame is appearing in the 2005 documentary “Word Play,” in which he has one speaking line. “I have it on DVD,” Piscop says.
Bagel, coffee, puzzle
Piscop has written a book about how to solve Cryptic Crosswords, which are even more challenging because solvers have to decipher the clues before they can work on answering them, and he wrote “Mensa 10-Minute Crossword Puzzles” and several page-a-day crossword calendars. He’s also one of the judges for the annual America Crossword Puzzle Tournament that Shortz runs in Stamford, Connecticut.
He runs a website called MacNamarasband.com where he posts a free puzzle every week. He was a Washington Post crossword puzzle editor from 2002 to 2008, and he became editor of the USA Today crossword puzzles this year after a plagiarism scandal there dogged the former puzzle editor.
Piscop’s got a set morning routine: He walks to Dunkin’ Donuts in Bellmore where he has a plain, multigrain bagel and a cup of black coffee and does the cryptic puzzle in Britain’s The Guardian newspaper. “Sometimes I don’t even solve the whole thing,” he says.
For the past decade, he’s been living in an apartment at the home of his niece Katherine Stein, the daughter of Piscop’s younger brother. When Stein’s brother got married, Piscop constructed a puzzle for the occasion. “I gave him a list of facts about my brother and his wife-to-be,” Stein says. “Their college mascot, where they met. We all did it at one of the bridal showers.”
Stein says Piscop has co-opted her dog, Dina, a rescue Chihuahua mix, that now lives with him. “He spoils her rotten,” says Stein, 36, a financial planner. Piscop also plays in the Long Island Senior Softball Association league, jams on keyboards on Tuesday nights at Katie’s of Smithtown and drives his 94-year-old mother to church on Sundays.
“I do my puzzles, do my best to stay in shape, play music, walk Dina, and look after my mom,” Piscop says. “Things are very simple now.”