The Necessity of Filling Certain Boxes

by Ross Trudeau

           The pain usually starts in my lower back and flashes down the sides of my legs, and when it gets really bad, Jessie asks me if I want her to get her chainsaw. I always smile; it’s a funny bit. It started years ago when she deadpanned the question and offered to perform an amateur living room amputation of my legs. Now, as then, I smile-grimace and nod, and she sighs and feigns weariness and rises from our bed to retrieve the hardware. 
           As she leaves the room, I think of the phrase “gallows humor.” I think of “palliative care,” and a Mary Oliver poem I haven’t read since college. What’s it called? “Death Comes?, I think. Maybe “Death Arrives”? 
Jessie returns with a glass of wine and sets it on my nightstand. “Do you want to solve the crossword?” 
           I’m staring into the middle ground, mouth slightly open, shaking my head slowly. The pain is still deep and sharp but now somewhat blurrier around the edges. Is it “When Death Arrives”? Jessie kisses me on the forehead and smiles. She learned to recognize this expression of slack intensity years ago, and slides back into bed beside me. 
           I sit up and reach for my laptop at the foot of the bed, and wince as the change in position draws my attention back to the pain. Jessie, lying next to me again, asks, “Got a crossword idea?”
           “Got a crossword idea,” I say, opening a blank document and typing out a line:



           My diagnosis came in November of 2001, when my classmates and I were still walking around our Manhattan prep school in a persistent post-9/11 miasma. It was nearly Thanksgiving, after the smell had lifted and President Bush had reopened Yankee Stadium with a ceremonial first pitch, when an MRI revealed a benign olive-sized tumor in my spine. I was initially diagnosed with Schwannomatosis, a genetic disorder involving an inactivated tumor suppressing gene. But when I started developing dozens and then hundreds more angiolipomas scattered all around my body just beneath the skin—a symptom not commonly associated with Schwannomatosis—my diagnosis became hazy. A specialist at NYU Medical Center told me that he’d never met anyone like me. 


           It’s definitely called “When Death Comes,” I tell myself, and I count the letters in the title. W-H-E-N-D-E-A-T-H-C-O-M-E-S. 14 letters. The idea that’s burbling up is too macabre for a mainstream crossword, but even that awareness doesn’t interrupt the internal mechanism playing out irresistibly in my head. When. When suggests temporality, chronology. Year, day, time, hour, second. I reach for the wine and sip. Death. Synonyms for death. Euphemisms for death. Rest, eternal rest, expiration, departure, passing.
           WHEN DEATH COMES. I stare at the phrase. Rest, expiration, departure, passing. Year, day, time, hour, second. And then I’m typing the phrase EXPIRATION DATE—yes, also 14 letters long!—the same moment it comes to mind. The cursor blinks. A moment later I’m typing DEPARTURE TIME. 13 letters. 
           I’m still in pain, but I’m not looking at it, inside. The pattern resolving in front of me arrests my attention. I just need one more answer, a second 13-letter answer, because like the mind, crosswords demand symmetry above all. And then the phrase PASSING MOMENT snaps into focus, and I count the keystrokes as I type: P-A-S-S-I-N-G-M-O-M-E-N-T. 13! A wave of abiding satisfaction suffuses me down to my toes as I consider the words in front of me. 



           I went in for my first surgery a week before Thanksgiving, 2001. The surgeon promised me that removing the tumor from my spine would relieve some of the pain immediately; the specialists were quick to point out that I might develop new ones at any time. When they rolled me for the first time to the operating room, my mom walked calmly next to the gurney, holding my hand. When I came to a stop under the clinical glare of the discs of OR lighting, a blue-clad female anesthesiologist materialized above me. I’m told that I, already drugged, blurted out, “Mom! Smurf!”
           “No, sweetie,” she’d said. “That’s Smurfette.”
           Smurfette asked me to count backwards from ten as my vision went black. 
           I can’t trace my waking memories post-surgery to any fixed point. I’m told I was awake within a couple hours of the conclusion of the six-hour procedure, but what I can remember are more like feelings or impressions than actual memories. At some point it registered that I’d had surgery. Post-op treatment details cohered: I’d been given multiple antibiotics since waking, morphine for the pain, Benadryl for the itching caused by the morphine, Zofran for the nausea caused by the Benadryl. But my central nervous system couldn’t support anything like a fixed train of thought, and I remember at one point settling on the terrifying notion that I’d gone insane, and my disordered, half-waking, half-sleeping reality would persist forever. 
           But the world reordered itself, slowly, by degrees. And within ten days, once the jagged, nine-inch incision on my lower back had closed, once I’d regained feeling in my lower body, I was ready to leave the hospital. The morning of my discharge, with my parents at the bedside holding my arm, the surgeons told me that while the surgery had been successful, they’d also found another tumor—too small to operate on—and that I may need to start thinking about chronic pain care.  


           “Oh, that’s good.” Jessie is looking at my screen. “The first three are phrases that can be reinterpreted as when death comes.” 
“You should reorder them. If it goes DATE, then TIME, then MOMENT, it’s like you’re zooming in to, like, the very last second.”
           I look at Jessie, who’s wearing a small closed mouth smile. She’s an autodidact who started making her own crosswords some months after we began dating. I lean to kiss her on the forehead, and the pain hardly registers. “You just wrote all the clues,” I say, and I start typing again.  

           EXPIRATION DATE (14)              [Last day?]
           DEPARTURE TIME (13)               [Last minute?]
           PASSING MOMENT (13)             [Last second?]
           WHEN DEATH COMES (14)      

           “There it is, baby,” she says. “A tight, consistent, utterly morose set of theme answers for your depressing crossword puzzle.”
           I smile, and open my crossword software, and place the answers in the grid, each pair of equal length occupying symmetrical slots: a standard crossword has 180-degree rotational symmetry, which means it’d look just the same if you turned it upside down.


           Over the years I experimented with a variety of pain management strategies. Yoga routines seemed to work for a while, until they didn’t. Neurological pain drugs weren’t effective, and left me in a dense cognitive fog. Meditation practices felt like they only made things worse.  
           The low emotional ebb came when I was teaching high school English in San Francisco in 2011, when I uncapped a sharpie in front of my bathroom mirror and began circling each of the subtle bumps that dotted my torso, arms, and legs. I remember feeling defiance, maybe anger, as I started in on my left arm: seven circles, ranging from pea-sized to larger than an olive. The five circles on my right arm, drawn with my left hand, were sloppy and irregular, especially the one delineating a tiny new lipoma I found on the triceps above my elbow. My torso took only a matter of seconds, since I was keenly aware of the location of each of the fourteen bumps that, more often than any of the others, I unconsciously prodded and rolled in the minutes before sleep or between sets at the gym. Here I paused to look at my naked reflection in the mirror and began to cry. In retrospect, I knew from the outset that I’d weep, that this was no exercise in empowerment or control. It was an expression of self-pity, a giving up. The first disgorged sob of a long, surrendering cry that persisted as I continued circling the largest bumps (lower back), the most emasculating (inner thighs), the most noticeable (above the knee). 
           By the time I’d finished I was sitting on the floor, hidden from the mirror but not the fluorescent ceiling bulbs, the ink on my back imprinting faint purple circles on the side of the tub. I spat on my left forearm and started rubbing at one of the circles near my wrist. Pressing down on my lipomas like this didn’t exactly hurt, but evoked a nails-on-chalkboard discomfort. The lesion that I imagined that caused the real, unignorable pain was the small one in my spine, clinging to the angel hair pasta of woven nerves at my L4 vertebra. Sitting on the bathroom floor as I did sent a synesthetic lightning bolt down the outside of my right leg, a unique sensation at the intersection of an overdeep stretch and a broad, achy bruise. 


          Jessie has by this point nodded off. Even more than when I’m developing a theme for a crossword, building and filling the grid sinks me into a fugue state in which the pain recedes to some more distant quarter of my awareness. Time has dropped away too: I don’t know how long I’ve been at it, or how long Jessie’s been asleep.  
           I tab unconsciously between rows and columns, adding black squares, scanning for constrained crossings. The grid begins to take shape: not too many closed-off sections, some long entry slots for fun non-thematic answers. I add FLOPPY DISK, and PRO-GAMERS. A whole corner falls easily, with fun entries like IRON MAN and RASTA. I wonder if the “R” where the proper nouns DREXEL and ARLO cross will be a challenging square for solvers. I come to a complete halt in a section that seems unfillable with valid entries, until the name RIRI bails me out.

           I yawn and look at my watch. It’s 2:00am, and the pain has subsided to the point where I slide my laptop to the floor, put my head on the pillow, and am asleep next to Jessie within a minute or two.


           When I started making crosswords as a hobby in the summer of 2015, it was largely because of how pleasurable it was to develop lists of words that expressed an interesting linguistic pattern. I’d been an inveterate word nerd from a young age, favoring Scrabble over Monopoly, causing my father to wince with bad puns, and anagramming every collection of words that entered my field of vision. On our first date, I pointed to a NO PARKING sign and suggested to Jessie that the words could be scrambled into the phrase A PORN KING, in which she delighted, to my great relief. 
           The pattern-seeking became habitual. On a dinner date with Jessie in Mission Hill, I wondered how many places have names that comprise a religious facility and a topographical rise. Boston’s MISSION HILL, Jerusalem’s TEMPLE MOUNT, Gettysburg’s SEMINARY RIDGE, Yosemite’s CATHEDRAL PEAK. And as a kicker, I hit upon a phrase that can be reparsed as a cutesy descriptor of this pattern: MORAL HIGH GROUND. 
           On that same evening, Jessie exhorted me to one more drink, doing a quick sidewalk arabesque and singing, “The night is young!” 
           My face slackened. The night is young. THE NIGHT IS YOUNG.
           “Oh no. What is it?”
           “CHILD STAR!”
           “The night! It’s young! Get it? CHILD STAR! And … BABYMOON! And, uh … oh! MINOR PLANET! There’s a crossword theme here!”
           It was only after I’d begun selling crosswords to newspapers that I began to reflect on why I’d thrown myself so completely into the avocation. Yes, I found it rewarding and fun, but much of the time, I realized, it was a coping mechanism. When I found myself in pain, standard distractions like watching television didn’t tend to help: sitting and watching was too passive, and my attention would inexorably return to the hurt. On the other hand, more demanding tasks—grading my students’ papers, reading a novel—asked too much of me. I couldn’t devote the critical focus to the task. 
           But making crosswords, I came to realize, occupied some sublime cognitive space at the intersection of entertainment and rigor. My attention could share a space with my pain. I couldn’t ask it to leave, but rather to sit next to me, tracing its bony finger down the length of my sciatic nerve, and looking at my computer screen, rather than directly at me. 


            It’s morning, and I’m pouring coffee while “Windows” plays over the radio. An NPR host is saying that Chick Corea has passed as I review last night’s grid on my laptop, shaking my head. I know it doesn’t stand a chance of seeing daylight in a mainstream crossword venue. When you open The New York Times, the puzzle makes two implicit promises to you: first, that unlike the other problems and headaches you’ll face today, this problem has a solution—perhaps an elegant and satisfying one. And second, that when you enter the little compartmentalized reality of the crossword, you won’t have to be on guard against the stressors, triggers, and anxieties of life outside the grid. You won’t see SPINAL TUMOR or UNTREATABLE PAIN as an answer word. You won’t have to dwell on Chick Corea’s passing by filling in WHEN DEATH COMES. Relax, the puzzle says. You’re safe in here
           Jessie appears over my shoulder, kissing my ear.
           “You’re never going to sell this one.”
           “I know,” I say, setting the coffee pot down and exhaling. “It hurts again this morning.”
           Jessie grunts her sympathy and hugs my shoulders. “Let’s make another one,” she says, squeezing tighter. A jazz piano riff fills the silence. 
           After a while, I say, “How many famous people besides Chick Corea have a young animal in their name?”
           Jessie snorts a small laugh. “RYAN GOSLING. Hottie.”
           “JOEY RAMONE.”
           “Don’t forget KIT HARINGTON,” she says. 
           “This isn’t a bad theme idea. It needs a title.”
           We stand there, thinking, with little curls of steam rising from our mugs. After a few moments Jessie smiles and looks at me. “Men,” she says, kissing me gently on the forehead, “can be such babies.”

77 thoughts on “The Necessity of Filling Certain Boxes

  1. Fantastic essay Ross, and best of luck with your surgery tomorrow. Your puzzles have always stood out to me for their levity, so it’s surprising to learn about the pain behind them.

    I realize it’s not the same as your physical pain, but I took up crossword constructing as a hobby around the same time that my wife suffered a miscarriage. A lot of what you wrote really resonated with me. I don’t think I had the self-awareness to understand how much crossword construction helped me cope with the emotional pain, but reflecting on your words has given me a better appreciation for that, so thank you.

    • It sounds like we’ve got this in common, D. It was really Jessie who prompted me to consider what was going on around the house. I hope the puzzling helped; I can’t imagine what that was like. My parents miscarried themselves before my twin sister and I appeared on the scene. Best wishes.

  2. I can understand why Wordplay picked the quote they picked, it’s really just the perfect description of what constructing does in one’s brain. Glad to have read this. Best of luck with the surgery. Looking forward to solving your next beer can someday soon!

  3. Ross – hilarious, inspiring, insightful and devastating. I hope tomorrow goes well and that you’re back home soon, to further baffle and amuse us. Warm wishes for a joyous holiday with Jessie and your family, and for strength and good health in the New Year.

    Best from South Florida!

    • So glad to hear from the Florida contingent — thanks for dropping a line, Alan! Presumably next week’s puzzle will veer hard in either the baffling or amusing direction… TBD. Happy holidays to you!

  4. I never have had occasion to look at your blog other than on Sunday mornings when the new-puzzle emails prompt me to. It was only a fat-finger on a browser button that caused me to open it today and read your essay, learn about your condition, and hear of your upcoming procedure. I hope it all goes well and that you have a speedy recovery. You seem to be in a pretty good mental place.



    • Thank heaven for those fat fingers! I debated sending this out as an email, but I’m wary of spamming loyal solvers such as yourself, Rich. Tomorrow should be a piece of cake. I’ve got Jessie and Ruby and the Daily Crossword roundup email. What more does a man need? (Oh, more theme material! Thanks!)

  5. Your essay is brilliant and your openness a gift. Thank you for revealing your story to your devoted followers! Wishing you all the best, as always.

    • Thank you, Nancy, and wonderful to hear from you. Openness around these issues was a hard-won thing for me; it means a lot to get this sort of feedback. My best wishes to you as well.

  6. Great essay! I discovered you on Twitter early in the pandemic when solving more crossword puzzles than I normally would took my mind off Covid. Thanks for sharing this with us. Good luck with the surgery. ❤️

    • Thank you, Rachel, that means a lot. I think crosswords experienced a little golden age there when so many of us were casting about for order and distraction. I hope they brought you some.

  7. I’m part of your dad’s cohort. (A girlfriend transferred to be part of the first coed class at Yale in ’69 and introduced me to College Paper Doonesbury.) So I have the additional resonance of imagining my son going through this pain. I wish you all the best, and thanks for all the puzzles.

  8. Thanks for sharing this piece, Ross. It was beautiful to read. Sending kind thoughts your way. I started watching Cursewords last fall and it brought me so much joy during what were pretty dark times for me. I hope these messages from your readers/solvers provide you even a bit of the comfort you’ve so generously shared with so many of us.

  9. Thanks for sharing so much of yourself in this beautiful essay. Putting the words in the box is quite different from assembling them artfully into sentences and paragraphs. But in both ways, you are quite gifted. I hope tomorrow’s surgery brings you some measure of respite.

  10. Nicely written. I suffer from chronic (24/7) pain from a broken neck. My experience is a bit different — when my pain is low, creative pursuits and intense work like writing code will sometimes take my apparent pain down a notch, sometimes allowing me to forget the pain for a while … until I pause. Like you, passive activities never do that for me. But, when I’m going through an episode of greater pain, nothing really helps. I hate those times. People sometimes ask me “if you’re hurting all the time, why are you working so hard?” I guess the situation seems backwards to most people.

    • Roy, great to hear from you. I’m a personal fan. I’m sorry to hear of your troubles. And, yes, I can relate. Sometimes there’s just nothing for it. Except, perhaps, for being in conversation with other folks who can relate. Thanks for dropping by, and all my best wishes.

  11. I had a tumor growing rapidly in my uterus during my first pregnancy. When it outran its blood supply and sort of died back, it was really painful. Unwilling to take medication, I learned self-hypnosis, which works well if you can get ahead of the strong pain. Once you achieve it, you still have the pain, but in the state of altered consciousness, you sort of do not care. I am impressed that you discovered this on your own, plus you create puzzles–cool! Pulling for you!

      • A psychologist from the Children’s Hospital who worked with young cancer patients using self-hypnosis coached me in the technique, which he also called ‘deep relaxation.’ Sometimes you have to hunt, but other times serendipity drops just the right practitioner in your lap. That ‘baby’ is now 41, so those months are long past–just not forgotten. I will say that in old age, something is hurting all the time, so just ignoring it and delving into my hobbies helps. Hope your are healing well.

  12. Would have been a better boss had I read this in 2011. Great writer. Great teacher of writing.

    How about that Giant baby? Colt McCoy.

    • Jason, you were a remarkable boss, and (if you’ve forgotten) you always supported me without even asking why I needed this or that accommodation. It’s wonderful to hear from you. All my best wishes to your family!

      Colt McCoy. Amazing. Add it to the list.

  13. You are one of my favorite puzzle constructors. Thanks for sharing your story.

    We have been binge-watching Dickinson recently, and I think Emily would appreciate the gallows humor of your puzzle. (If you haven’t seen the series, Wiz Khalifa as Death in a ghostly carriage is simply brilliant.)

    Wishing you all the best on your surgery today.

  14. Thoughts are with you today, Ross. All best for the procedure and recovery.

    By the way, STEPHEN FRY, or is that a little fishy?

  15. As someone who is still struggling to have my first puzzle published (so many rejections!), I’ve always envied your puzzles, especially your grid work. And as a former newspaper editor and someone who really appreciates good writing, I admire your ability to put one sentence after another and craft a very compelling (if heart-wrenching) essay. Best wishes to you, and thanks for sharing yourself with us.

    • Thank you for your kinds words. And as for the rejections, I amassed a couple dozen before ever selling anything to a newspaper. My email is in the sidebar; I’d be happy to consult if you ever want a fresh pair of eyes on your grids.

  16. Best wishes. Thanks for writing this.

    I’ve enjoyed your puzzles and the Zoom presentations you’ve given on crossword construction.

    • It’s entirely my pleasure, Eric. Those pandemic puzzle zooms have been an absolutely essential way to connect with the outside world for me in the last couple of years. I’m glad you found them useful.

  17. We can’t know someone else’s pain. But once we’ve seen the bravery and endurance of the people we love who suffer from it, we know them, respect them, love and cherish them in a way we couldn’t possibly feel for anyone else.

    • Too true. I count my blessings every day, as many of the sufferers of what I have are young children whose paths are much rockier than mine has been. Those little guys are the ones I’ve long looked to for lessons in bravery and endurance.

  18. “Making crosswords…occupied some sublime cognitive space between entertainment and rigor.”
    You write such an elegant essay, fully rounded and deeply truthful. Thank you for revealing so much about yourself and your relationship with Jessie and with words. You brought this insomniac relief and pleasure.
    Good luck with this operation, I wish you peace and surcease from pain.

    • I’m doing really well, Tamara; thanks for your kind words. It took me a long time to get comfortable talking about this stuff. I always felt like I was going to risk overburdening the people around me. But the puzzling community (and Jessie, of course, among many others) has really shown me the real capacity for care and empathy out there. We should have to be afraid of being vulnerable, and that’s a piece of wisdom I cherish. Thank you stopping by.

  19. our paths are not similar at all, but your description of the state of focus that pushes back the day’s worries and pain really resonates today. my wife and best friend passed away a little over a month ago. the moments (like your 12/13 NYT puzzle) each day that establish sharp contrast with the blur and haze of much of the rest of my day are regular, welcome moments of clarity. thank you sincerely, and I wish you well.

    • I’m sorry for you loss, Matt. It’s striking how many people come to puzzles in moments of hardship or loss, and equally encouraging how many of those people find community in the puzzling world. Many of my closest friends these days are people I found through crosswords. Thanks for saying hi.

  20. What a gift to discover this essay today, Ross. Your words resonated very strongly with me. I began solving the NYT puzzle every day day five years ago during a very rough period, and I started constructing last year. Doing so has helped me work through midlife anxieties and survive the Trump presidency – nothing like a practice of creating some order in the midst of chaos each day!

    My wife has become very familiar with my need to unscramble the world into clever phrases of 15 letters or less, and I love knowing that there is another couple out there having similar conversations. Best wishes on your journey!

    • Thank you, Jeff–it’s nice to hear from you here. I think the “creating order from chaos” appeal is the most universally attractive element of puzzling, and boy howdy, the last couple of years probably turbocharged that appeal for a lot of us. Thanks for dropping in!

  21. For what it’s worth, I love your puzzles, and now have a greater appreciation of the inspirations behind them Hope your surgery goes well, and that we can all look forward to the continued enjoyment of this hobby that we love.

  22. Beautiful writing – it is a gift.
    As a Cambridge resident, I also love your local references.
    To you and Jessie – as you recuperate (and any time) please don’t hesitate to reach out if there is anything I can do – I make great soup!!

  23. Thank you, Ross. You are inspiring. I knew that before, but now I know it better. Your essay helped me in more ways that you can ever know. Thank you. And thank you, Jessie.

  24. Good luck my new friend. You understand the true nature of acceptance. That there can be pain without suffering. It is work and work and work, but it is good work.

  25. Ross,
    This heartfelt essay is as engaging and well crafted as your puzzles. Thank you for sharing so many intertwined parts of your life in one read. Thank you too for the encouraging and helpful advice you’ve given me as a new constructor.
    So glad to hear the surgery went well.

  26. Thank you Ross, for sharing your story, your puzzles, and your pain. Our hearts are with you, and with Jessie.

  27. I always enjoy doing your puzzles! A while back one of your clues was “538 host” and I was so pleased that I knew the answer to be Galen Druke. I live in Cazenovia, NY and my son graduated from Cazenovia HS with Galen. I also know his father, John from my involvement with progressive politics. I was sure you must know Galen. I emailed his dad and told him it was so cool that Galen was in your puzzle. Imagine my surprise when I found out that neither John nor Galen knew about the clue and that Galen hadn’t ever met you! His Dad was unfamiliar with you at all & had to google your name. You put smiles on all of our faces. I hope you’re doing well. Thanks for the puzzles.
    Martha Moore

  28. Hi Ross, my wife and I have been enjoying your crossword puzzles for the past few years and it somehow seemed incongruous that we didn’t know this about you. That is, of course, absurd. We don’t know you and have never met but since we’ve started solving we’ve developed a sense of the person behind the puzzle and there’s never been a hint pointing to what you outlined above. We’re both sorry that you’ve had to spend time traveling such a challenging and painful path. Thankfully you are not traveling alone. I just wanted to write to let you know that Beth and I have made a lunchtime habit of filling in squares during the work week and after Sunday’s regularly scheduled French toast breakfast. Throughout the pandemic we’ve enjoyed your individual and collaborative work and the sense of bringing order to chaos that solving them provides. Thank you.

    P.S. I think our dog Ollie enjoys solving too but his contributions are few and far between :/

  29. Like many, I suppose, I stumbled into crossword solving during the pandemic and the NYT version has become a daily habit bordering on obsession to solve without the use of Google. I have to say I enjoy whenever I see your name on the byline, Ross, as I know it will be a satisfying solve with usually a few laughs along the way. Thanks for sharing your personal story and all the best in the road ahead. I do wish, however, that the NYT would publish puzzles with darker themes, this would would have been great fun to unpick!

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