Doug Hoylman was strictly a numbers man by trade, calculating costs and risks on Geico insurance policies. Off duty, he immersed himself in the twists of language — jokes, puns and other visual queues and clues that could help him figure out, for example, four-letter words to describe “a bad day for Caesar” or a “male raccoon.”
He was a habitual crossword-puzzle solver and a six-time winner of the American Crossword Puzzle Tournament, the most prestigious contest of its kind. He was tied for second place for career wins. In addition, Dr. Hoylman was a competitive Scrabble and Trivial Pursuit player.
Dr. Hoylman, 72, died Nov. 2 at his home in Chevy Chase, Md., across the street from the Geico office where he worked as an actuary for more than 20 years. The cause was heart disease, said a friend, Ted Gest.
Will Shortz, the crossword puzzle editor of the New York Times who founded and directs the American Crossword Puzzle Tournament, wrote in an email that Dr. Hoylman “never got stuck on a puzzle.”
“Doug was also notable because of his cool, deliberate manner of solving,” Shortz added. “His nickname was ‘Iceman.’ When you’d watch him on the big board during the playoff round, he seemed to be moving so slowly that you’d think he couldn’t possibly win. So you’d watch the other contestants instead. Then you’d look back and Doug would be way ahead of everyone else, and you’d think, ‘How’d he do that?’ ”
Typically, Dr. Hoylman told The Washington Post almost 30 years ago, he completed 20 to 30 crossword puzzles a week, always starting methodically at square one in the upper left-hand corner and proceeding diagonally downward in an orderly manner to finish at the bottom right.
“The only way to practice is to do a lot of them,” he said, “but I’m not a fanatic. I like problems that have neat answers. In our daily lives you deal with problems that have no definite answers. You might think you have a good answer to a problem, but you’re never sure. In crosswords, there is always a right answer.”
Douglas John Hoylman was born July 2, 1943, in Kalispell, Mont., where his parents ran a heating and air-conditioning business. Growing up, he was a voracious reader, according to his younger brother, Richard Hoylman, his only immediate survivor.
From a young age, Dr. Hoylman was a self-described “typical nerd” and “a solitary kind of person.” On Friday afternoons during his boyhood and teenage years, he would check out an armful of books at a local library. Monday mornings, having read them all, he’d return them to the library.
He skipped a grade in high school, according to his brother, and received a bachelor’s degree in mathematics from the Massachusetts Institute of Technology in 1964 and a doctorate in mathematics from the University of Arizona in 1969.
He settled in the Washington area about 1970 and retired from Geico in the 1990s.
He began competing in crossword tournaments in the mid-1980s by filling out a qualifying puzzle, and he won his first tournament in 1988. His other championships came in 1992, 1994, 1996, 1997 and 2000. He also had three second-place finishes and three third-place finishes. This year, he finished in the top 40, which is said to be highly unusual for a man of 72.
As a Scrabble player, Dr. Hoylman competed in 81 tournaments between 1993 and 2009, said Gest, who directs the Washington unit of the North American Scrabble Players Association. Dr. Hoylman’s best single performance was in 2006, when he won a divisional title.
His trivia expertise came in handy in 1999 when a friend and crossword competitor, Trip Payne, appearing on the TV game show “Who Wants to Be a Millionaire,” asked for Dr. Hoylman’s help.
The show has a “phone-a-friend” option for guests who are stumped. Payne, unable to identify where “Unabomber” Ted Kaczynski once taught mathematics, turned to Dr. Hoylman, who correctly identified the University of California at Berkeley.
Having competed against Dr. Hoylman in crossword tournaments, Payne described his style of play in an email message: “He’d just be filling in one square, then the next, then the next. But the thing is, he never paused — so before you had any idea what had happened, he had quietly said, ‘Done’ and won the tournament yet again.”
As easily as describing the “Ides” as a “bad day for Caesar” or “boar” as a male raccoon.