By Jack Crosbie

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President Donald Trump has, in the past three years, retweeted white nationalists, British Islamophobes, American Islamophobes, QAnon conspiracy theorists, Pizzagate conspiracy theorists, and, on Aug. 13, a man named Shashank Tripathi, who does not fall into any of the prior categories but is still a weird dude for the president to toss an RT to.

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Tripathi is not particularly well-known by his real name. But online, he’s a legendary figure in the annals of trolling: A Twitter power-user who goes by @ComfortablySmug.

Tripathi has had many lives: In the mid-2000s, he described himself as a “hedge funder,” and honed his talents of online shit-stirring in the comments section of New York magazine’s website and a little-known insiders’ financial blog.

For years, Smug was a largely benign function of the burgeoning Twitterverse, one of several anonymous, media-friendly, vaguely political posters who would spar and snark with members of the New York and D.C. press online.

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But like many obscure characters of the internet, the high drama of the always-online 2016 election cycle catapulted users like Smug back into political relevance, and he quickly reinvented himself as a scion of the Trump-friendly mainstream web.

In recent years, Tripathi has embedded himself at the center of a swampy posting nexus that exists to create a steady stream of shitposts that prop up the Republican party line—basically, ground zero for all the memes that end up on Boomer Facebook a month later.

ATTENTION MINIONS:



Joe Biden is a moron.



He held up signs the other night.



Enjoy pic.twitter.com/ZU0uFavviI — Comfortably Smug (@ComfortablySmug) April 22, 2020

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In the Trump era, this strategy has paid off.

Tripathi has always been a troll; but now he’s an incredibly influential one, often popping up in Donald Trump Jr.’s feed, occasionally getting play on Fox News, and watched closely by Trump insiders like Dan Scaviano.

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But his status as an original denizen of the blogosphere and early Web 2.0 means that he’s also still friendly with a cadre of longtime Democratic politicos and a decent amount of the D.C. and New York press corps. These are not, typically, the kind of people who would necessarily like to be associated with a person who sells Christmas sweaters that say “Own the Libs,” shirts that say “Beto is a furry,” and coffee mugs that dream about Ruth Bader Ginsburg passing in his Teespring store.

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And yet—here’s Lis Smith, the mastermind of Pete Buttigieg’s insurgent campaign for president, palling around with Smug over cat pictures on the internet.

Ok this was your best Christmas tweet — Lis Smith (@Lis_Smith) December 26, 2018

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What makes Tripathi’s brand relatively unique is that “owning the libs” is about as controversial as he gets.

His Twitter bio claims that he is “#altcenter,” and though his posts are openly conservative, they rarely plumb the depths of the reactionary denizens of the online alt-right, the loose collection of conservatives that harbor white nationalists. In other words, Smug has apparently realized that as long as he strays away from the more distasteful parts of the alt-right’s platform (open racism) he can keep advancing conservative ideas without alienating D.C.’s ideologically vacant middle ground.

On the greater web spectrum, he’s slightly to the right of Barstool Sports, and marginally better behaved. His intended audience is roughly the same—young men who work office jobs and lean conservative, but who haven’t spent quite enough time on 4chan to go full reactionary.

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Smug’s posts toe the line between laughing at Trump’s excesses while venerating his actual policies.

Walking that line has helped make him tremendously influential.

The tweet that caught Trump’s eye wasn’t exactly a masterpiece— it was just a passing quip that most power-users make multiple times a day. Tripathi replied “Ok Fredo” to a Tweet by CNN anchor Chris Cuomo, who was apologizing for losing his cool on video to a man he accused of being racist toward Italians. Trump, no fan of Cuomo’s, hit the RT button, probably thinking little of it.

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For Tripathi, it was a massive feather in his cap. He posted a screenshot of it to Instagram, a platform he only sporadically uses, where it got 650 likes.

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For someone with a true poster’s heart, like Tripathi or the president, clout is everything.

Politics and posting have always connected: In the early 2010s, his Twitter bio included a link to donate to Mitt Romney’s 2012 campaign. Federal Election Commission (FEC) records show that he donated a total of $541.99 to Romney throughout the 2012 election cycle. (In the 2020 cycle, his only contribution has been $1 to Mike Gravel’s campaign, another masterclass in posting.)

In 2012, Tripathi also made his only real attempt to get involved under his own name: He got a job as the campaign manager for Christopher Wight, a financier who challenged Rep. Carolyn Maloney (D-N.Y.) for New York’s 12th House District. Wight’s campaign was a long shot, which is often how up-and-coming operatives cut their teeth: If they get a contender to outperform the spread in a losing district, their next job might be in a more competitive race or staff position in the future.

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That job was derailed, however, by the biggest moment in Tripathi-as-Smug’s posting career.

In the early 2010s, Smug had a few thousand followers on Twitter, including some of New York City media’s elite, which was then an even more insular and less-widespread bubble than it is now.

But even then, the platform’s ability to quickly disseminate news made it stand out among slower services like Facebook and Tumblr. When Hurricane Sandy hit the city in October 2012, news about the city spread like wildfire on Twitter, with personal users and official accounts all publishing minute-by-minute information to scared residents looking for news. Behind the Smug account, Tripathi saw a chance to cash in on his favorite currency: attention.

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Throughout the night, Tripathi tweeted several false rumors, including that Con Edison was shutting down all power in lower Manhattan, that Gov. Andrew Cuomo was trapped on the island and being taken to a secure shelter, and, most notably, that the floor of the New York Stock Exchange was under water.

The last one in particular spread widely, eventually ending up on CNN and the Weather Channel and sparking several beats of on-air commentary before it was debunked.

Unrecorded

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Smug was admonished but didn’t face any real consequences for the stunt until he was exposed a day later by Jack Stuef, a contributor at BuzzFeed, who linked pictures posted to Smug’s social media accounts to accounts under Tripathi’s real name.

This was before “doxing” was in widespread parlance, but Tripathi’s name was certainly newsworthy, as he’d just attempted to spread disinformation during a natural disaster for clout. At the time, Stuef told the Daily Dot, this was before Twitter’s verification system was widespread. Having a lot of followers and palling around with journalists and media types on Twitter conveyed a sense of authority to an account like Smug’s.

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“I think he was kind of in a weird space. He had been seen as an authority on what was going on, and [people] trusted what was coming from him in the same way that they would have from a reporter,” Stuef said. “But there was no transparency there, he could always hide behind the anonymity. There was no sense of responsibility to the people he was tweeting to.”

After the Sandy tweets, that trust was clearly broken. “I didn’t think he deserved that anonymity,” Stuef said.

Tripathi resigned from Wight’s campaign immediately. Wight lost to Maloney in the general election and declined to comment for this story. Tripathi, after being called out by multiple national news outlets, went into a self-imposed Twitter hiatus until March 2013, at which point he popped back up to stay.

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He was welcomed back by his online crew, a collection of pseudonymous finance bro accounts, many of whom contribute to a niche finance blog called Stone Street Advisors. (The blog has been shuttered for years and did not pay contributors; its founder now runs an independent consulting firm under the same name, which is not affiliated with Tripathi.)

Tripathi may have flamed out of politics under his own name, but the Smug persona came away mostly unscathed.

After all, it’s not like any of what he did was out of character: The Smug persona has, above all, always been willing to post anything for a reaction.

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Tripathi’s first foray into internet notoriety was as a prolific commenter on New York magazine’s website, which cultivated an online community around its blog posts and articles in the early 2000s. Tripathi, as Comfortably Smug, was heavily involved, commenting several times a day—1,449 times, as of an interview with him on the site in 2009, and was one of the most prominent voices in a certain crowd of young wannabe alpha-males who stood out in the site’s online ecosystem.

“There was this sort of posse of finance guys who, I don’t know what they did during the day, but they clearly weren’t doing much, because they had time to comment on New York mag websites and send emails or private messages to 20-something N.Y. mag editors,” Arianne Cohen, a former freelance editor who worked for the magazine at the time, told the Daily Dot. “What they all seemed to have in common was they were very interested in themselves and wanted the spotlight, but due to their job could not publicly identify themselves.”

This was around 2008-2009, a mostly lawless time online when Facebook was expanding beyond college campuses. Tripathi and his cohort had a private Facebook group, which he moderated from a profile under his pen name. New York editors called him Smugs or Smuggles in private conversations, as he quickly became one of the more recognizable voices on the site.

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Tripathi did not respond to a request for comment from the Daily Dot.

The messages and emails Cohen mentioned were just the start: At one point, she said, he sent another editor a gift basket. He frequently offered to meet up with young female editors in person, and seemed bent on initiating personal relationships with the people who wrote and produced the content he interacted with online—emailing editors personally to ask for favors, offering to show up at book signings, sending notes on personal Facebook pages.

In other words, he and many of his peers had “serious boundary problems,” as Cohen put it. “He could be equally insightful and emotionally brutal,” she said, two traits he leaned into while seeking engagement online.

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For years, New York gave him what he wanted, including his crown jewel, an entry into the magazine’s Sex Diaries, a popular still-running column where New Yorkers wrote a week-long candid account of their sex life. Tripathi’s column—which Cohen edited—is one for the ages: A tale so filled with stimulants and emotional abuse that it makes you worried for everyone involved.

11am: I’m completely worthless — I can’t find the napkin with the lesbian’s number on it. Plus I ended up getting dragged to some diner when I was drunk. I’m going to have to take more Adderall to curb my appetite so I don’t eat today to make up for it.

3pm: I’m on the Facebook profile of the Only One That Mattered, my most pathetic habit. I’ve been prescribed Wellbutrin pretty much since we broke up. I hate days when my thoughts turn to her—it hurts but fits in with my many masochistic tendencies.

The Sex Diary eventually led to an interview and photoshoot, which Cohen says she was not in the office for. She avoided ever meeting Smug in person.

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Over the years, Smug’s online circle grew, and strangely, his notoriety faded. The man who once tried to sow additional chaos to the city’s worst disaster in over a decade assumed his place as a playful trickster in political and media circles, regularly interacting with a cadre of New York media types like Yashar Ali, and D.C. politicos—the aforementioned Lis Smith, for instance, has tweeted at Smug nearly 200 times since 2014, including many times during Buttigieg’s run.

White chocolate isn't chocolate it's total bullshit . cc: @ComfortablySmug — Yashar Ali 🐘 (@yashar) August 23, 2017

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You really love me, don't you. Thank you. @andylassner just yells at me all day. I don't know what love is as a result. — Yashar Ali 🐘 (@yashar) May 6, 2019

@ComfortablySmug don’t worry, I got you covered on sweet eclipse photos pic.twitter.com/A8jvTzDZ3j — Lis Smith (@Lis_Smith) January 21, 2019

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The fact that Smith’s interactions with Smug have gone unnoticed are a testament to how well he’s ingratiated himself into the political elite, considering the inevitable outrage that would erupt if, say, Sen. Bernie Sanders’ national press secretary Brianha Joy Gray was palling around with Carpe Donktum.

Smith did not respond to questions about Smug.

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Tripathi has always leaned conservative, and his irreverent, post-first-and-often style made him the perfect internet citizen to benefit from Trump’s presidency. But rather than go full-MAGA, Smug’s brand online focuses mainly on “owning the libs,” making him amenable to both the Federalist-loving super-conservatives and more moderate D.C.-types. His profile now includes a disclaimer, in the form of a pinned tweet from 2017: “This is a joke you fucking morons.”

His co-conspirator in all of this is Matthew Foldi, a 23-year-old University of Chicago graduate who was elected as the Republican committeeman for Chicago’s Fifth Ward (which largely covers the university) at age 19. Foldi parlayed his teen-elected official status into a succession of non-profit and PAC jobs, most recently as the rapid response director for the Congressional Leadership Fund. Foldi did not respond to a request for comment. The CLF declined to comment on the record but denied that Tripathi was employed by or associated with the organization in any way.

Online, however, Foldi functions largely as Tripathi’s handler, the bridge between his still-“guarded” real identity and the legion of “minions” who follow Smug online. Foldi organizes and helps run events with Tripathi, like D.C. trivia nights and other meetups, which attendees are allowed to publicize on social media as long as they do not photograph Tripathi.

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Since widespread lockdowns went into place across the U.S., Tripathi’s community has shut down IRL events but is still flourishing online, hosting online movie nights and trivia competitions.

Most of this activity is innocuous—a misfit gang of conservatives enjoying the company of other people with account names like “Mr. Nuclear Cocaine.”

But Sen. Ted Cruz (R-Texas) is now a fan, recently challenging both Foldi and Tripathi to the #CombatCOVID19Challenge on Twitter and retweeting Smug several times.

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Cruz’s office did not respond to a request for comment on the senator’s relationship with Tripathi.

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By now, you’ve most likely noticed that “No comment” is a common response when you ask people about Tripathi. Smug has influence online, at least insofar as the micro-community of hardcore “minions” is concerned, but also because he now rubs shoulders online with people who have real-world power.

The GOP knows that people respond well to irony and jokes, particularly those that target an easily identifiable group. Tripathi is more than happy to play along: Recently, his hobby horse has been the Chinese government’s role in spreading the coronavirus pandemic, which is Trump’s new scapegoat for the U.S. response.

Tripathi’s new audience, the movers and shakers of the conservative digital web, are far more receptive to his advances than the 20-something magazine editors at New York were. They’re willing to use him for what he offers: A platform still watched by the media and political elite, that’s fluent in the language of the internet used by the GOP’s most lackluster demographic (young people).

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Yet like the editors who dodged him in the early aughts, nobody wants to go on the record about Smug and call Shashank Tripathi a friend.

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