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He has said that his favorite crossword of all time is the Election Day crossword of November 5, 1996, designed by Jeremiah Farrell. In 2013, Shortz lent his name and talents in puzzle writing and editing to a new bimonthly publication entitled Will Shortz' WordPlay, published by Penny Press.

In February 2009, Shortz helped introduce the KenKen puzzle into The New York Times.

The lucky player is picked randomly from a group of submissions containing the correct answer to a qualifier puzzle issued the week before. Shortz is also weekly guest on NPR's Weekend Edition Sunday where he hosts the Sunday Puzzle, a cooperative game between the show's host and one of the show's listeners. He founded the World Puzzle Championship in 1992 and is a director of the U.S. He is the founder of the American Crossword Puzzle Tournament (1978), and has served as its director since that time. Shortz has been the puzzle master on NPR's Weekend Edition Sunday since the program was started in 1987. A few months later he became the crossword puzzle editor for The New York Times, the fourth in the paper's history, following Eugene Thomas Maleska. He was rehired in late 1991, then let go in August 1993. Shortz began his career at Penny Press Magazines, then moved to Games magazine for 15 years, serving as its editor from 1989 to 1990, when the magazine temporarily folded. He is a member and historian of the National Puzzlers' League. Shortz is the author or editor of more than 100 books and owns over 20,000 puzzle books and magazines dating back to 1545, reportedly the world's largest private library on the subject. He also earned a Juris Doctor degree from the University of Virginia School of Law (1977), but did not sit for the bar exam and began a career in puzzles instead. Shortz achieved this by designing his own curriculum through Indiana University's Individualized Major Program. Shortz wrote his thesis about the history of American word puzzles. He eventually graduated from Indiana University in 1974, and is the only person known to hold a college degree in enigmatology, the study of puzzles. At age 16, Shortz began regularly contributing crossword puzzles to Dell publications.

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He was drawn to puzzles at an early age in eighth grade he wrote a paper titled “Puzzles as a Profession.” (The paper earned him a B+.) At age 13, Shortz wrote to Language on Vacation author Dmitri Borgmann for advice on how to pursue a career in puzzles. Will Shortz was born and raised on an Arabian horse farm in Crawfordsville, Indiana.

Shortz's American Crossword Puzzle Tournament is the country's oldest and largest crossword tournament. After starting his career at Penny Press and Games magazine, he was hired by The New York Times in 1993. He graduated from Indiana University with a degree in the invented field of 'enigmatology'. Shortz (born August 26, 1952) is an American puzzle creator and editor who is the crossword puzzle editor for The New York Times. New York Times Puzzle Editor (since 1993), NPR's Weekend Edition Sunday Puzzle master (since 1987)