Adjunct math professor by day, puzzle maker by night, Derrick Niederman has devoted a lifetime to the art of problem solving.

by Jason Ryan
Photography by Peter Frank Edwards ’93

The man on the airplane was scribbling furiously on the trans-Atlantic flight, enough to provoke the interest of a seatmate. Sneaking a peek, she noticed he wasn’t correcting legal briefs or reviewing spreadsheets, but rather editing a crossword puzzle of his own design. Soon enough, curiosity, or the boredom so easily found within a cramped fuselage at 30,000 feet, got the better of her. Unable to contain herself, the woman blurted out a question she needed resolved before the plane’s touchdown: “Excuse me, sir, but are you Will Shortz?”’

No, alas, the mystery man was not the famed puzzle maker, but what a coup it would have been to be seated beside Shortz, the crossword puzzle editor at The New York Times, former editor of Games magazine and a subject of the 2006 documentary Wordplay. Despite this disappointment, the woman was not unfortunate in her seat assignment. Funnily enough, the mystery traveler beside her was a pal to Shortz and a world-class puzzle creator in his own right, one who was unwinding from competing in a European bridge tournament by making crossword puzzles on his seat tray. And though he didn’t star in Wordplay, this passenger did have a cameo – and, speaking of movies, some people just swear he could be a stand-in for actor Chevy Chase, at least the Chevy Chase preserved on VHS in so many 1980s screwball comedies.

Movie-star looks, an intellect on par with America’s most famous puzzler, international bridge player extraordinaire with a habit of mid-flight crossword-puzzle editing – Why, who is this man?


Perhaps you’ve seen the commercials: A handsome, suave, bearded Latino gentleman urges viewers to drink Dos Equis beer as short vignettes of absurd adventures flash across the screen: an Ernest Hemingway lookalike drops out of a plane in a vintage kayak, casually shoos a pet cougar off his kitchen table, ferries half a dozen smiling beauty pageant queens in a lifeboat in rough seas, cavorts with royalty and skin-dives for a chest of sunken treasure, all while a narrator touts the virtues and accomplishments of this bon vivant who regularly disarms the two sets of creatures that habitually surround him: wild animals and beautiful women half his age. As the narrator informs us,

He is the life of parties he has never attended.

He once had an awkward moment to see how it feels.

His mother has a tattoo that reads, “Son.”

On every continent in the world, there is a sandwich named after him.

He is, the narrator concludes, “The Most Interesting Man in the World.”

Yet there is a rival in the wings, a man whose intellectual and athletic pursuits are similarly whimsical and awe inspiring, though they have yet to be televised. And like his fictional beer-promoting counterpart, this man has a regular audience of young women, too, though they meet him not in a dim bar, but a sunlit classroom in Maybank Hall, dressed not in cocktail dresses, but shorts and T-shirts, with bookbags slung across their shoulders. There, he urges these women (and a handful of men, too) not to “stay thirsty, my friends,” but, rather, to remain steadfast in their problem solving.

The T-shirted men and women are his students, and little do they know that the man at the front of the classroom is much more than meets the eye, that they are under the tutelage of someone who is many things other than adjunct math professor, including champion squash player, financial wizard, bridge enthusiast, game inventor, author of 12 books and, most distinguishingly, master puzzler. Distracted by polygons and models of linear and exponential growth, these students might pass the class but fail to realize they are in the company of a very special teacher, someone who, beer commercials aside, might truly be the most interesting man in the world. Or at least be in the running.

The promise of such distinction was not evident early in his life, when Derrick Niederman was born into an existence that seems, on a superficial level, in lockstep with the culture and lifestyles of typical New England bluebloods and Ivy Leaguers. He grew up in the pastoral Connecticut countryside as the son of an epidemiologist renowned for helping identify the root cause of mononucleosis. Niederman graduated from nearby Yale University before studying at the Massachusetts Institute of Technology, where he earned a doctorate in mathematics and studied under legendary mathematician Irving Segal. During these years, he played squash competitively, earning the No. 1 spot while at Yale and becoming the sport’s top-ranked amateur. In time, he’d become national amateur squash champion for the 35-and-over crowd.

After MIT, he began a career in finance, first working as an analyst, then, by 1987, as an investment columnist for Fidelity in Boston. The transition to financial writing hinted at his future as an author, and, in 1995, his first book, This Is Not Your Father’s Stockpicking Book, was published. He’d follow that up in later years with two other investment books, including one that doubled as a murder mystery: A Killing on Wall Street. Niederman’s drift into book writing was a symptom of frustrations in his finance career, most notably the lack of creativity required for his work and the ever-shrinking time frame used to evaluate investments. Niederman’s investment approach was “old-fashioned,” meaning he would prefer to check on his recommendations every couple of months to monitor their progress. Many peers, however, were more vigilant, perhaps to no advantage, becoming increasingly sensitive to daily ups and downs. He was leery of these trends and the inevitable influence it would have on his life and career.

“Many people in the financial business have their lives dominated by forces outside their control, although theoretically one can control one’s responses,” he says. “I didn’t think I was well equipped to be immersed in a business in which I would be defined by a performance number, and a performance number only. The more I allowed myself to be defined this way, the less happy I would be.”

One thing that did make him happy was puzzles, which he was no longer simply solving, but also creating.

After a few years of experimentation during graduate school as a means of procrastinating against writing his thesis, at the age of 26, Niederman had his first triumph, when The New York Times published one of his crossword puzzles. He had been rejected three times before by the crossword puzzle editor at the time, Eugene T. Maleska, who warned him to allow some time to pass before pestering the paper with another attempt. But the bold and relentless Niederman submitted another puzzle just three weeks later. Lo and behold, Maleska accepted, making Niederman a very happy man.

“As soon as I published a puzzle in The Times,” he says, “I felt I wrote the first line of my obituary.”

Unfortunately, crossword puzzles don’t pay the bills, even those published in The New York Times. Niederman recalls earning about $100 for that first published puzzle in 1981, necessitating him to keep his day job as a financial analyst. Despite the meager payout, the puzzle earned him considerable acclaim and attention, as did the themed crossword puzzles he continued to get published in the Sunday edition of The New York Times – about 20 in the last 30 years. Yet his newfound fame also subjected him to a bit of contempt, such as the time a colleague passed Niederman and boasted with an air of derision, “I solved your puzzle.” Niederman was baffled, not so much at his rudeness but for the fact that his rival seemed not to realize that solvability was the point.

“Whoever he was, he continued on his way, pleased at winning the joust, evidently not realizing that most crossword makers want people to solve their puzzles,” writes Niederman in his latest book, The Puzzler’s Dilemma. “Otherwise, we wouldn’t go to all that trouble to make the words intersect.”

Yet for all Niederman’s elation at his accomplishment in puzzledom, there was also uncertainty.

OK, now what? Niederman recalls thinking following the publication of his first crossword puzzle.

He plowed ahead in his finance career, though he was careful to take note of some nagging doubts in his life about the value of his assorted pursuits. His dissertation on the infinite orthogonal group, for example, he judged to be an unworthy result of that many years of his life. At work, he sometimes swam against the tide, unwilling to mirror the intensity of his colleagues and their focus on the short term. Peggy Malaspina, who worked alongside Niederman at Fidelity before becoming his romantic partner for the past 20 years, recalls how he initially infuriated her with his casual habits. She and most of their colleagues often worked 80 hours a week without batting an eye.

“Not Derrick. If he had a squash game at six, he was leaving,” says Malaspina, explaining that her perspective of Niederman’s work habits has since changed. “He was pretty clear he had balance in his life, and I give him credit for that.”

In 1995, at age 40, Niederman had had enough. He quit his job and took a gamble, signing on with America Online to write mysteries for Internet audiences he hosted in a chat room each weekend, answering their questions about his whodunits and offering clues. It paid for him to make the mysteries both interesting and challenging – the longer the hundreds of cybersleuths stayed in the chat room, the more money Niederman and AOL both made. This change in professional direction also offered him the chance to focus his energy on what had been his true passion in life: puzzle making.

“Once I felt I had done my time in the financial business,” Niederman says, “I gave myself the freedom to return to puzzles, which I always loved the best.”


Walk through Niederman and Malaspina’s home in Charleston and you’ll find it hard to leave. Around every corner a puzzle or game is lurking, waiting to drain the hour, and your brain. Among them are a bag of plastic polygon puzzle pieces named Pentagone – a TV-themed board game and a hybrid of Connect Four and Scrabble that stands tall on a coffee table. All these prototypes are Niederman’s creations. Many required hours and hours of careful cutting, pasting and painting to make; others are professionally constructed by using 3-D modeling. In the last two decades, Niederman has taken dozens of these games to major toymakers and trade shows, hoping to score a hit. Despite their ingenuity, many were not deemed suitable for mass production. A handful, however, have been successes, and in recent years Niederman has hit his stride in the game world.

In December, Games magazine named Pathwords, Niederman’s word-search game featuring puzzle blocks similar to the shapes in Tetris, the best word game of 2012. Its manufacturer, ThinkFun, is now working to make a Pathwords app for the iPhone and induced Niederman to produce a kids’ version and a German version, too. In 2008, ThinkFun produced Niederman’s 36 Cube puzzle, which is a three-dimensional adaptation of the 36-officer problem posed by the 18th-century mathematician Leonhard Euler. Unlike Euler’s officer problem, Niederman’s 36 Cube isn’t impossible, though it might seem like it. Players of 36 Cube, which is sort of a mix between Sudoku and Rubik’s Cube, must stack small plastic towers of assorted sizes and colors onto a pronged grid to form a cube.

Niederman is adept at creating all sorts of puzzles, whether involving words, numbers, shapes or suspense. Oftentimes it is a combination of some or all of the above, such as in the mysteries depicted in his book Inspector Forsooth’s Whodunits. These puzzles, games and inventions do not come easy to Niederman – except when they do. Niederman invented Pathwords in 10 seconds as he walked down the stairs of his home. Yet a perpetual calendar he’s invented, which he describes as “a soccer ball with all the hexagons thrown out,” took him months to create. The calendar is a dodecahedron, or 12-faced object, featuring one month on each face. As the calendar changes each year, its user replaces transparent blue and red lenses on each face to cover up certain tinted dates that no longer coincide with certain days of the week. It’s an invention that’s difficult to describe, much less devise. What’s worse is that no one really needs a perpetual dodecahedral calendar these days, a fact that Niederman recognizes but finds “annoying.” He wishes “everyone went ballistic over it.”

“It solved a problem that people weren’t necessarily looking to be solved, namely designing a perpetual calendar that only needed to be reset once each year,” says Niederman. “That’s its shortcoming.”

Such frustration can be all too common for puzzlers and inventors, and, no matter their prior successes, there is always disappointment over the things that fall short. Niederman is no exception.

“He takes on challenges,” Malaspina says, “and is hard on himself if he doesn’t succeed quickly and perfectly.”

But when Niederman does succeed at these challenges, the results are impressive. Some of his boldest work has been in the form of crossword puzzles, and he is praised by no less than Shortz for his “grand ideas” in this medium.

Shortz speaks fondly of Niederman’s “Smooth Move” puzzle that was published in The New York Times in January 2005. It incorporates two chessboards within the crossword grid, and a number of answers within the chessboards contain the names of chess pieces, such as Kingston or weeknight. The two different arrangements of these clues/pieces within each chessboard then help the solver determine a final answer: checkmate.

“It’s just a crazy thing to try and do, and Derrick pulled it off,” says Shortz, who each week is inundated with about 100 crosswords made by Times readers, yet only able to publish seven.

Also of note is a crossword puzzle Niederman submitted to Shortz that features two sets of entirely different answers that fit the same grid and clues. Shortz determined this construction to be “an almost impossible challenge,” and, indeed, he has not yet accepted this puzzle, hoping Niederman can make a few improvements.

But Niederman isn’t completely consumed by puzzles and games. He’s also managed to keep his love of mathematics alive, writing two books on numbers for mainstream audiences: What the Numbers Say and Number Freak. In the former, Niederman and co-author David Boyum (who happens to be a squash buddy) analyze figures we encounter in our everyday lives and suggest how to interpret these data and numbers in meaningful ways. In the latter, Niederman explores the numbers 1 to 200, offering up an astounding smattering of thought-provoking and quirky tidbits. Consider his entry for 108, which, Niederman logs, is the number of degrees in each angle of a regular pentagon, the number of suitors courting Penelope in The Odyssey, the number of stitches on a Major League baseball and the number of cards used to play a game of canasta. Writing such math and number books for a broad audience is challenging, but Marian Lizzi, editor-in-chief of Perigee Books (an imprint of Penguin), who this year published Niederman’s The Puzzler’s Dilemma, says Niederman pulls off the feat with aplomb, walking a fine line to satisfy the mathematically inclined and disinclined alike.

“The depth of understanding he brings to his subject matter sets him apart from the pack,” Lizzi says. “He has a great deal of enthusiasm for the material, which comes through in his conversational writing style, so that the reader feels almost like Derrick is explaining the material one-on-one.

“Editing Derrick’s books has opened my eyes to many surprising connections and hidden patterns all around us,” she continues. “The experience has also reminded me of how impactful it is to write with passion. There’s no substitute for an author’s enthusiasm when it comes to grasping new ideas and truly absorbing them.”


Niederman and Malaspina moved to Charleston on a whim. Tired of miserable March weather in New England, the couple made a brief escape to Charleston in 2010, renting an apartment in the historic Joseph Aiken Carriage House on Charlotte Street. In the course of a month, they fell head over heels for the Holy City and, in August 2011, they made a permanent move into another downtown home. Unwilling to meet people “by walking the dog,” Niederman offered his expertise to the College and was hired as an adjunct professor for the 2011–12 academic year.

“The fit has been terrific,” Niederman gushes. “My colleagues in the math department have been so helpful, both personally and professionally.”

But more important than the social opportunities provided by the College’s faculty community was the chance to teach mathematics – and communicate his passion for the subject – to students.

“As you get older,” Niederman says, “you get more conscious of what you can do for the younger generation.”

Just like his book audiences, Niederman’s mathematics classes are filled with both those with strong aptitudes for mathematics and those for whom numbers can cause nightmares. He sympathizes with students’ fear of mathematics, and regrets that a poor introduction to the subject can often permanently poison the numbers department in young minds. What’s lost, he believes, is a student’s ability to gain and maintain the confidence, resiliency and innovative habits necessary to tackle so many things in their professional and personal lives.

“Life is a succession of problems to be solved without being encumbered by the succession of problems,” Niederman says. “Mathematics offers students an opportunity to enhance their question-and-answer skills for any subject. An inadequate foundation in mathematics results in students never living up to their actual problem-solving potential.”

College students are receptive to these philosophies. Remy Teicher, a rising junior and theatre major from Bernardsville, N.J., credits Niederman for making mathematics interesting and practical, but also challenging.

“I really lucked out with him. His teaching methods are definitely geared for people not into math,” says Teicher, who counts herself among that population (or at least she used to). “He’s just a cool dude, and you want to listen to him.”

Niederman peppers his classes with jokes and asides that distract from the drier aspects of lessons. Teicher says these diversions are appreciated, and she is grateful for his patience and calm, casual teaching style.

“It’s more motivating. I feel like I’m doing the work for myself,” Teicher says. “I feel like he’s on our side.”

Niederman, of course, is unable to prevent his puzzle-making tendencies from creeping into his teaching, even if the effect is subtle. Reviewing answers to a quiz with his class this past spring semester, Niederman confessed that in labeling the vertices, or corners, of a polygon with consecutive letters from A to G, he was unable to resist skipping the letter F as “a lame attempt to create some kind of obstacle.”

“Oh, so you did that on purpose?” one student replied, apparently unfazed.

“Yes, it was on purpose,” said Niederman, with a twinkle in his eye. “Did you wonder about that?”


So, back to our question: Who is this man, and is he the most interesting man in the world?

For Niederman to lay claim to that title, would it help if he had cut his own umbilical cord at birth? That he can divide by zero? That Bigfoot has a blurry picture of him, or that he has never lost a thumb war?

No, that kind of hyperbole is better suited for people devoid of true merit, such as make-believe adventurers in beer ads. Real men of interest don’t have to exaggerate their accomplishments. Indeed, if their accomplishments are sufficiently impressive, embellishment only results in farce. Though you may not see Niederman in a beer commercial anytime soon, you could sit beside him on an airplane. If you do, ask to make his acquaintance, and don’t confuse him with another puzzle maker. For he is Derrick Niederman. And that should be enough.