JONATHAN KAY is planning his attack on German forces in Meximieux, France, as his opponent, a talkative Bay Street accountant named John McDiarmid, describes the many intricacies of Advanced Squad Leader (ASL), perhaps the nerdiest board game ever invented. On the boardroom table is an old Harvey’s mug (their makeshift dice tower, to eliminate all odds of cheating) and a tiny spool of pink thread used for tracing soldiers’ lines of sight. Had Walrus staffers not already left for the weekend, they would sneer as he stops, mid-argument, to retrieve the ASL rulebook — a 600-page biblical tome — from his office. Kay competes in international ASL tournaments a few times a year. In October, upon his return from an ASL tournament in Cleveland, he bragged about having played for 14 hours in one day “with barely a nod to even the most rudimentary aspects of nutrition and hygiene.” The 48-year-old thinks of nothing else when he plays: “I don’t have this constant static of family, tennis, work, writing, social media, email, my boss.”

Kay is an eminently distracted, nicer-than-most contrarian-turned-public-intellectual. He started the top editorial job at The Walrus in December 2014 and promptly transformed its digital presence, making it more relevant to the daily news cycle. He’s infused its pages with opinions diverse and, at times, offbeat. He’s fought to make the magazine less cautious, and has nurtured an office culture where disagreement is common. “I wanted ordinary, intellectually curious, educated people to open my magazine and go to my website and find all sorts of things that surprised them, and sometimes shocked them,” he says. “When The Walrus first came out, I felt like it was talking to intelligent people, but it wasn’t talking to intelligent people like me.”

Kay was recruited from the comment pages of the National Post because The Walrus needed someone different, someone digitally savvy, to shepherd its operations onto tiny screens and infinite scrolls, and because it wanted to appeal to ordinary and opinionated readers like Kay. He was a far-from-obvious candidate, but also one determined to transform The Walrus into a clearing house for the most pressing and provocative ideas. It’s been over two years since he took over. There have been some successes, but hardly the revolutionary change he keeps talking about.

BETWEEN QUESTIONS, Kay sips his coffee and averts his eyes. Sitting at the Patrician Grill on King Street East in Toronto, where he eats breakfast three or four times a week, he’s wearing his usual grey, slightly wrinkled suit. Without warning, he lifts his empty plate over our booth and onto an adjacent table. Once outside, he tells me why he enjoys this quiet 1950s-style diner: “I’m a little bit anti-social.” Normally, he arrives around 8:30 a.m., orders eggs and toast with bacon or sausage, and grabs a booth near the windows. If he’s meeting someone, he’ll pay the tab before either has asked for the cheque. His first time at the restaurant, Terry Papas, one of the owners, recognized him as “that guy on CBC.” Intrigue turned into anger when Papas caught him cutting up what he thought was one of the restaurant’s complimentary newspapers with an X-Acto knife. It turned out that Kay had brought his own copy of The New York Times. During his first years at the Post, he constantly cited the Times during editorial meetings; to this day, he will circle, in black or red pen, “fantastic” or “useful” paragraphs from Times articles and tweet pictures of them to his more than 17,900 followers.

Kay generally keeps to himself, but Papas can draw you a sketch: “He doesn’t like fancy.” In fact, he’s “like your grandfather.” Easily satisfied. Very utilitarian. He’s a Sears suits type of guy, the kind that devours power bars — not because he likes them, but because they’re the most efficient way of re-energizing. On ASL night at the Walrus office, Kay offers to order pizza, even though he doesn’t know of any nearby pizzerias. “You’re the one who works here!” McDiarmid says. “But I’m a member of the elite,” Kay quips. “I don’t eat mere pizza.” They eventually send a friend, who has arrived to watch them play, to fetch a few slices. When he asks if Kay prefers a fancy option, like three-cheese, he replies, “Look, if there’s an 11-cheese option and a seven-cheese option, go with the seven.”

Once, Papas heard Kay mumble he prefers work over weekends. Those who know Kay personally wouldn’t be surprised. On the day of his ASL match against McDiarmid, the editor attended Google Canada’s Go North event in Toronto and filed a 1,200-word piece on Shopify. At some point, he bungled sipping coffee — a rubbed-out stain extended down his blue-striped shirt. After taking a seven-day, all-expenses-paid trip to Taiwan at the invitation of its Ministry of Foreign Affairs (with the intention of writing about it someday), Kay spent the following week attending the Giller Prize Gala, composing an election-themed limerick for the Washington Post, penning columns for The Walrus and the National Post, flying to Ottawa to interview Governor General David Johnston, appearing on The National’s “Sunday Talk” with Wendy Mesley, emceeing a charity event at the Metro Toronto Convention Centre, hosting a book club talk on Justin Trudeau’s memoir, Common Ground, at Soho House Toronto, and leading a conversation on the dangers of prescription drug abuse at a Walrus Health Leadership Dinner.

Wherever he goes, he brings his sales pitch: subscribe to our magazine and visit our website. “Editors never used to be so visible to their audience or intimately engaged with them,” says senior editor Jessica Johnson. “I don’t know who Jon’s equivalent would be.” She says The New Yorker’s David Remnick is of a different generation. “You know he’s there, but he’s not, like, tweeting about what he ate for dinner.”

Jeffrey Goldberg, editor-in-chief of The Atlantic, is Kay’s closest equivalent. A divisive figure in his own right, Goldberg writes as much for The Atlantic — if not more — than Kay does for The Walrus. More importantly, their successes reflect the changing role of magazine editors. When David Bradley, owner of Atlantic Media, announced his decision to hire Goldberg in a memo to staff, he wrote: “The editor-in-chief of a great publication is asked to be a public figure, a live performer, a leader of talent, a driving news force, a culture commentator, a long-form editor, a cover story genius, a packaging genius, a digital strategist, a social media practitioner, a video producer, a new product creator.” In the end, “The selection of an editor becomes a question of which virtue to privilege.”

When John Macfarlane announced his retirement from The Walrus in August 2014, he had spent six years as its editor-in-chief. During his reign, the magazine’s stories began appearing on platforms beyond print. His replacement, according to publisher Shelley Ambrose, had to be “an editor of all things Walrus.” She hired Searchlight Recruitment, a head-hunting agency, and told them a digital mindset was imperative. “I got a call. Someone bought me lunch, told me to show up to an interview,” Kay recalls. “I was flattered, so I showed up.” He had never previously considered working for The Walrus.

KAY SHOWED PROMISE AS A WRITER in his early teens. When Barbara Kay, his mother and a columnist at the National Post, helped launch an annual contest called First Fruits at the Jewish Public Library, she encouraged “Jonny” to submit a piece; his essay on World War II earned first place. He spent his first four years of elementary school at Solomon Schechter Academy, a Jewish parochial school, before transferring to Selwyn House, an all-boys private school in Westmount, Montreal. At home, he was encouraged to engage in intellectual discourse. While young Kay’s thinking was more aligned with his mother’s, the more confident he became, the more they disagreed. “My family’s an acquired taste,” Kay says, noting that his father, Ronny, aspiring to casual dinner talk, bought an official three-fight boxing bell in New York to mediate their conversations.

“This was like running away to join the circus.”

After studying commerce at Marianopolis College, he decided to pursue degrees in metallurgical engineering from McGill University, followed by a law degree from Yale University. With friends from Marianopolis, he took road trips (or “dude trips”) that gave the bourgeoning intellectuals a chance to debate current affairs. These trips “were so formative in his development as a free thinker,” his friend Paris Valaskakis says. “He had an audience, and he could take risks with his positions.” At the time, Kay thought little about his future. He says he was lucky that his parents made a good living and paid for part of his education: “I had the privilege of being casual about this.”

That word — privilege — has clung to him and become injurious, even though, according to Ronny, his son’s “sense of entitlement is overwhelmed by his sense of responsibility.” In a 2015 interview with Canadaland’s Jesse Brown, in which he and Kay discussed the whiteness of voices in The Walrus, the editor argued that high-minded attempts to be inclusive by giving unqualified people a place in the industry “usually end up looking like ham-fisted experiments in affirmative action.” During his time at Yale, he made the same observation about efforts to address the racial imbalance on the Yale Law Journal’s editorial board. Kay once noted his fascination with “the way that public discussions of white privilege themselves become Exhibit A in how white privilege works.” His critics will point to his own comments about white privilege as exhibits A through Z. Even Johnson, who admires his kindness and open-mindedness, says, “My efforts to make Jon understand the plight of the disenfranchised have been very — not unsuccessful — but just not worth my time.”

As a writer, he will pitch some stories, such as a profile of Kevin O’Leary, based on conversations with upper-middle-class friends and interactions at the Toronto Lawn Tennis Club, a private tennis club in a tony Toronto neighbourhood, where he’s a member of the board. His non-journalist friends, however, defend his social awareness. Jennifer Bishop is the president of the board at the club and Kay’s tennis partner; she won a provincial championship with him in 2014. On more than one occasion, she has threatened to email Jennifer Good, his wife and a lawyer he met at McGill, asking her not to let him wear certain clothes on the court. One shirt with an eight-inch alligator on its breast was particularly bothersome, but as a matter of principle — it was a gift from his Filipino nanny — he insisted on wearing it.

KAY’S FIRST JOURNALISTIC BIG BREAK, a review of the movie Independence Day, was published in Saturday Night magazine in November 1996 while he was working as a tax lawyer at Goodman Phillips & Vineberg in New York. When Ken Whyte, editor of Saturday Night at the time, became founding editor of the National Post, Kay’s name resurfaced as a candidate for its new editorial board. The interview was like nothing he’d ever experienced. After asking him about his journalistic ambitions, Whyte began reading the newspaper, presumably to see if Kay could comment on the daily news. “I came out of the interview thinking, ‘Not only did I not get the job, but the guy clearly regretted me even being in the same room as him.’” Shocked as he was to be offered the position, Kay said goodbye to his legal career and moved to Toronto.

His father, a metallurgical engineer working in finance, worried. He penned a 10-page letter to his son, warning him of the risks. Law had the promise of money and stability, his mother says. “To Ronald, this was like running away to join the circus.” Kay says his father’s concerns stemmed from his immigrant anxieties — an interpretation that has led Jon to believe that job insecurity is responsible for the lack of diversity in Canadian media. Jon’s grandfather moved from Siberia to China, where Ronny was born; having moved to Canada, Ronny feared his son would be downwardly mobile. “I read his letter with interest, but it didn’t shake my conviction,” Jon says. Thirty years old and looking to settle down, he was running out of time for risky career moves.

He arrived at the Post with no journalism experience, matching the make up of his colleagues. “The bosses actively wanted non-journalists,” says Alexander Rose, a founding editorial board member. “Not having a journalism degree was a feather in your cap.” Later, when Kay became comment section editor, he hired in much the same way. “He was not looking for the newest group of j-school graduates,” says Matt Gurney, who studied military history at grad school and freelanced for Kay before being hired full-time. Like Kay, Gurney would eventually climb the ranks and become comment section editor at the Post.

“People who are dogmatic leftists will see me as a despicable right-wing zealot, and those on the right will see me as a left-wing Trudeau apologist.”

Kay was the moderate voice on the board, especially after the arrival of Ezra Levant, whom he describes as “the guy you hate, but you come to respect in some weird way, and then you hate again.” Frustrated by Levant’s presence, Kay complained to Whyte, who responded with three words: “Ezra’s good coffee.” The sentiment has stuck with Kay, who believes that “every newspaper needs people who are good coffee. The Walrus needs people who are good coffee.” He doesn’t like Levant’s brand, but “there were some people who would have criticized The Walrus in the distant past for not having enough good coffee.”

His ambivalence toward perhaps the most controversial voice in Canadian media bespeaks his general two-mindedness. Kay worked as an editorial assistant on Levant’s 2009 book, Shakedown. Five years later, Kay helped Prime Minister Justin Trudeau write his memoir, Common Ground. A framed and signed portrait of Kay and the prime minister hangs conspicuously in his bare-bones Walrus office. “People who are dogmatic leftists will see me as a despicable right-wing zealot,” he says, “and those on the right will see me as a left-wing Trudeau apologist.”

In his own words, Kay is a “lapsed conservative.” He arrived at the Post an ardent believer in capitalism, and after the planes hit the World Trade Center in 2001, he wrote in his parting column that he had found his Spanish Civil War: “The fate of Western civilization was at stake. I was doing my best to save it, 750 words at a time.” But the failure of the Iraq War forced him to re-examine his cherished truth. In 2006, he penned “Confessions of a Misguided Hawk,” in which he renounced the “Bush- administration cheerleading” he had done over the years. He says, “That was the column that made me safe for left-wing dinner party society in Toronto.” It was the column that started getting him appearances on TV and radio. “I was seen as the guy who could give the conservative position, but to a certain extent in air quotes.”

Rather than fasten himself to any one dogma, the former columnist says he renounces the dangerous “habit of mind” that leads people to ignore the facts that confront them. It’s a habit he saw play out at the Post; again, while researching Among the Truthers (his 2011 book on the 9/11 Truther conspiracy movement); and again, every time a reader writes him a disparaging rebuke — to say nothing of the recent U.S. presidential election. Today, as though caught in ideological tug-of-war, Kay occasionally finds himself on Team Progressive, writing about the virtues of Nordic socialism and sharing his work on Facebook as his “latest left-wing propaganda for Walrus.

After years of being called a shill, he has cocooned himself in disregard for his critics. As editor-in-chief, he believes that he must juggle recognizing his audience — latte-sipping urbanites who care about the environment, travelling, and the arts — with creating a balanced, “wingless” magazine — and he doesn’t care who disagrees. He wants to “have a lot of different voices represented in my magazine,” he says, “not just the voices of Queen Street West bien pensants who all subscribe to the same email groups and Facebook pages and Twitter accounts and produce an echo chamber around much of Canadian journalism.” Sometimes, this means publishing rebuttals to pieces that appeared in The Walrus days earlier, or direct challenges to his own views. After making controversial comments on The National about Trudeau’s gender-balanced cabinet — turns out, he favours merit over quotas — he published Karen Ho’s “Meritocracy Is a Lie.” A day later, Kay noted in his response to the piece that both his Walrus colleagues and Twitter had disagreed with his position. “It was good old-fashioned ideological beat down,” he wrote. “But that’s life as a public quasi-intellectual.”

ON NOVEMBER 8, 2016, the night of the U.S. federal election, Kay was distraught and unable to sleep. He says he and Ambrose had been “crying on each other’s shoulders electronically,” and he was determined to file something — anything — on Trump’s once-unthinkable victory, even though it was two or three in the morning. “I was horrified that Trump won,” he says. “But I was also horrified by the prospect of people coming to the Walrus website and not seeing something about Trump.” The editor’s column, “The Trumpocalypse That Destroyed Conservatism,” did exceedingly well online, but it would be eclipsed later that day when The Walrus published Stephen Marche’s “Canada in the Age of Donald Trump.” At over 210,000 online views, the latter ranks among the magazine’s most-read stories. Ambrose must have felt vindicated. She had hired Kay believing that it would be easier to teach him about magazines than to teach an old-school magazine editor about the necessity of filing within hours of a presidential election. “The kind of news gene, that current gene, about what’s happening,” she says, “that’s where a newspaper background really comes in handy.”

A trained newspaperman, Kay arrived at The Walrus believing it had to live in the moment; making a “fetish of planning” would only get in the way. The idea soon crumbled under the realities of magazine publishing. In November 2015, Canadaland published a story containing a leaked email from Ambrose to Kay, dated September 10, 2015: “Dear Jon — I hate to do this by email instead of in person but we are in a bit of a melt down here … we have never been this disorganized and late shipping.” Further down: “I understand you are trying to build in flexibility and also to be as current as possible … but we seem to have thrown out the baby with the bath water.” In the same article, then-managing editor Kyle Wyatt claimed that Kay had killed more stories in 10 months’ time than Macfarlane had in four years. “I was embarrassed,” Kay says, “but it’s not like it was untrue.” Over a year later, he continues to be “ruthless” about killing stories in the name of protecting the Walrus brand. He doesn’t want editors “doing five drafts to save a shitty piece and turn it into a mediocre piece. I’d rather you do three drafts and turn a good piece into a great piece,” he says. “Editors are sometimes too hard-working.”

When word of the incoming bombshell got out, eyes rolled and staff members grumbled, but no one would, or could, do anything about it.

In journalism circles, there’s chatter of his unorthodox editing style. At the Post, he would routinely rip into columns written by unintelligible talking heads who were fine with the heavy-handed editing. But with polished magazine writers, he says, “They’re like, ‘I spent three months on this article and you just took a day and rewrote 5,000 words. Fuck you.’” Early disagreements made him realize he shouldn’t be a handling editor, so he relies on the “green light/red line” approach. At weekly editorial meetings, where, according to deputy editor Carmine Starnino, he is a “rogue element,” he sits at the head of a long boardroom table — the one used for ASL on Friday nights — green-lighting story ideas. On occasion, he’s invited outsiders, such as Amanda Lang, to attend and pitch. Handling editors are responsible for shaping stories without him “looking over their shoulder,” Kay says. To the annoyance of both writers and editors, his last-minute “red lining” sometimes involves inserting his own editorial voice.

He doesn’t always get away with it. “I’m not afraid to tell Jon that I think this is a dumb idea or that this is wrong,” says Johnson. “Anyone at the magazine will tell you that I do that on a daily basis — like, an hourly basis.” The senior editor says disagreeing with Kay is tiring, but, “If I can teach Jon, then we’ve gotten somewhere.” At other times, Kay pulls rank. On the day his now-infamous “Show Us the Suicide Note” piece was published, only Kay and maybe two other editors knew what was coming. In response to the Toronto Star’s decision to withhold publishing reporter Raveena Aulakh’s suicide note — a desire she had made explicit — Kay wrote that journalists should refuse to let suicide victims “impose control on the narrative of their broken life.” When word of the incoming bombshell got out, eyes rolled and staff members grumbled, but no one would, or could, do anything about it.

The incident, and others like it, have led to questions about Kay’s influence on the magazine’s editorial direction. In a series of Twitter essays, author and journalist Jeet Heer captured the mixed feelings many have about his sway. “Well, there goes The Walrus,” he remarked on the day it was announced that Kay would be editor, adding that the former Post columnist was an “anti-anti-racist” who would have fit well at a far-right magazine like The American Spectator or National Review. Four days later, Heer was again tweeting — only, this time, he argued that Kay “could be a great, game-changing editor” for The Walrus. In the past, the magazine had been “so quintessentially middle-of-the-road Canadian centrist,” he wrote, that someone like Kay (“brash, not afraid of an ideological fight”) was “a necessary corrective.” Kay’s strength lies in his ability to spark conversations that Canadians may be otherwise too afraid to have. Often, he plays the role of a contrarian — a game that comes with win-big, lose-big results. “If a piece hasn’t upended some pre-established notion, then the piece is a failure,” Starnino says of the editor’s style. “Each issue now has at least one or two stories intended to enter the reader’s bloodstream right away.”

Kay says his green-lighting of “The Highest Bidder” epitomizes the reason he was brought on. The May 2016 investigative feature identified the root cause of Vancouver’s soaring real estate prices: money was pouring into the market from China. Most Walrus editors at the table that day argued the piece would be perceived as racist. Kay didn’t care. He told The Globe and Mail’s Kerry Gold that he insists Walrus articles be “written in a candid style, without no-go zones.” She had to identify where the money was coming from. “My value,” says Kay, “is to be the guy who sits in this chair and says, ‘I don’t care who you’re afraid will be offended by that article, we’re running it because it’s a good article.’” Gold’s story was widely circulated online and is thought to have incited real change, with the British Columbia government having since introduced a one percent vacancy tax and a 15 percent foreign-buyer tax.

Despite its success stories, an onslaught of negative coverage has plagued The Walrus since Kay’s arrival — allegations of a “toxic work environment,” of editorial theft, of a push for “family-friendly” stories, and, most recently, of inflated circulation numbers. Canadaland reported in December that The Walrus’s paid readership has declined to below 40,000 — much lower than the 60,000 the magazine reported in two government grant applications filed in 2016. (According to Ambrose, the Canadian Circulation Audit Bureau’s report did not account for “additional non-traditional circulation,” such as sponsored-paid copies distributed at Walrus events.) Nevertheless, online page views are up 170 percent under Kay, and he and Ambrose are eyeing opportunities for growth as Rogers Media rolls back its print operations. “Our web traffic is a reflection of the fact that a lot of people aren’t just reading us, but hate reading us,” Starnino says. “We want to be relevant. And there’s no other way to be relevant.” Even Heer, in a rare instance of support for Kay, has tweeted, “The undeniable fact is the Walrus is now much more a part of the conversation than it was, say, 5 years ago.”

THERE WAS A TIME when Kay could have a beer with friends, watch TV, read a novel. But now he is in the Walrus office on a Friday night, confined to his self-made prison of perpetual productivity. He realizes ASL is the antithesis of productivity, but it “feels productive because it’s so intellectually engaging.” He sits on the edge of his swivel chair, the pink thread always within reach, discussing the upcoming ASL tournament in Albany, New York, until McDiarmid calls it quits, their scenario unfinished. During these bouts of intense game play, “My phone is beeping and buzzing and I don’t even notice it. I’m hungry, I don’t notice it. I’m thirsty, I don’t notice it,” he later tells me. In his writing, his choice of reading, his intellectual banter with colleagues, Kay is a man of ineffable intensity. “I always have to have my brain turned on 100 percent,” he says. “That has become my baseline for how I engage with life.”

Editor’s Note: On May 14, 2017, Kay announced his decision to step down as editor of The Walrus.

Correction: A previous version of this story incorrectly stated that Ronny Kay fled from Russia to China. It was not Ronny, but his father who moved from Siberia to China. We regret the error.

Justin Dallaire is the editor-in-chief of the RRJ’s spring 2017 issue. Follow him @JusDallaire.

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