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Trump and Tekashi: The Art of the Troll

How two New York provocateurs have broken our spirit with awful behavior

Getty Images/Ringer illustration

The crazy hair. The continual clickbait. The undeniable yet befuddling relevance. In the ongoing convergence between politics and popular culture, strange bedfellows continue to emerge. Though few are quite like this. Donald Trump, the first celebrity president, and Tekashi69 (a.k.a. 6ix9ine), the first mainstream troll rap star, have used a strikingly similar playbook to scale contemporary culture. They upend traditional news cycles, bend the media into stenographers of their exploits, and leave the masses — even when they know they’re being trolled — unable to look away.

Tekashi is difficult to describe in a single sentence, but here’s an attempt: He’s a troll, a trendsetter, a flash in the pan, largely unknown to anybody over the age of 35, and a felon whose music has been streamed billions of times in the past year. With 15 million followers on Instagram, he’s a nationally known local artist. But most importantly, he’s unpredictable. In March, The Ringer’s Donnie Kwak summarized his improbable rise as “an outrage magnet for our outrage culture.” In the ensuing months, that has only become more true.

While it’s almost a certainty that Donald Trump has never heard of Tekashi and Tekashi almost certainly has no idea who Mike Pence is, the parallels in their recent ascendancies are meaningful. Success in 2018 America has become increasingly defined by easily manipulated metrics. Instagram likes and view counts, while a bleak way to judge humanity, are a useful barometer for societal relevance. Content has, for better or worse, become more of a horse race, and this has seeped into our institutional infrastructure faster than anybody expected. One of the ironies of the coverage of both Tekashi and Trump is that the gatekeepers, who in the past may have attempted to block their gatecrashing, misjudged and ultimately underestimated the impact of their attention blitzes. They dismissed them for so long that by the time they finally realized what the numbers were telling them, it was too late. What we know now, and should have known three years ago, is that the more people talk about Trump and Tekashi, the more they win.

Here are just a few of the similarities that define them, and explain their bizarre rise.

New York

Both Trump and Tekashi are unabashed outer-borough New Yorkers, Trump from Queens, Tekashi from Bushwick, Brooklyn. Their geographical distance from the center of their industry universes — Trump the Manhattan real estate crowd, Tekashi the record label and entertainment PR machines — carved foot-long chips for each of their shoulders.

New York is important because a central feature in both Tekashi’s and Trump’s successes is talking shit. They are masters of the form. Nicknames, fake stories, an incredible ability to always have a response no matter how wrong they may be. This bravado is a New York City trademark, as old as St. Paul’s Chapel. That neither Trump nor Tekashi are actually popular with New Yorkers is meaningless. The two have been able to transfer the ethos — or the imagined attitude — of the city to the masses around the country.

President Trump Departs The White House En Route To Florida
President Donald Trump
Photo by Mark Wilson/Getty Images


When Trump announced his run for president in 2015, he was mocked by the political and media elite. He was given zero thought as a substantial candidate in 2016, and many think his initial desire to run was spawned from the humiliation of being the butt of many of President Obama’s jokes at the 2011 White House Correspondents’ Association dinner.

This anger at a perceived lack of respect for his accomplishments has persisted throughout his presidency. Everything from his inauguration-crowd size to Roseanne’s television ratings have been markers that he’s used to try to garner attention from the same media members and “elites” that he consistently bashes yet obsessively tracks.

When Tekashi first started releasing music in 2014, he was such a nonfactor with record labels that most of his early music was released by FCK THEM, a label in Slovakia. He made a calculated effort early in his career to lean into this so-called lack of respect from the music industry. If you can’t join them, piss them off enough until you beat them. He described this strategy — to become rap’s villain — to Mass Appeal: “’cause villains never die.”

Though his social following dwarfs much of the industry at this point, and his streaming numbers in 2018 (he’s released six straight top-100 hits this year) put him closer to Drake than Nicki Minaj, Tekashi has never performed any of his music on television. You won’t see him at award shows or other mainstream industry events. He’s rarely heard on radio and most of his press has been with outlets outside the mainstream. He craves respect, but not at the expense of attention.

Sexual Assault Charges

More than 22 women have described incidents of sexual misconduct by Donald Trump, dating back to the 1970s. The leaked Access Hollywood tape released just before the election in 2016, in which he boasted about “grabbing women by the pussy,” was a political shock but hardly surprising when you consider his history.

Unlike Trump, Tekashi didn’t escape criminal prosecution for his misconduct. He pleaded guilty to use of a child in a sexual performance after a 2015 incident in which he filmed and posted a video of himself and a friend assaulting an underage girl. He was sentenced to probation for the charge last month.


Dating back to his days as a showy real estate tycoon/media personality in the ’80s, Trump has always been the king of the stunt. He has called up newspapers pretending to be his own publicist, brought Bill Clinton’s assault accusers to a debate with Clinton’s wife, and most recently, sent thousands of troops to the U.S.-Mexico border for no reason right before the 2018 midterm elections to draw support from his base. He’s a master of cracked optics. Though he’s been president for nearly two years, he still holds rallies around the country on a weekly basis, usually at a private airplane hangar where he can fly in, use Air Force One as a backdrop for his speech, and fly right back out.

Tekashi’s tactics have been no less effective. When threatened by Chicago rappers Chief Keef and Lil Reese, Tekashi flew to Chicago and walked across the South Side while live-streaming on Instagram, daring anybody in the city to take a shot at him. He has pulled similar stunts in Los Angeles and Houston. In 2017, he faked his own death, uploading a video of himself to Instagram in a hospital bed covered by a white sheet. His tactics are at best obnoxious and at worst dangerous. But they consistently accomplish his ultimate goal, which is to get attention.

Photo by Bob Levey/Getty Images


One of Trump’s most undeniable characteristics is his willingness and seeming desire to fight with anybody who disagrees with him. An incomplete list of his recent feuds includes LeBron James, Jeff Sessions, Beyoncé, Stormy Daniels, the NFL, a union leader in Indiana, Ted Cruz and his wife, California firefighters, anybody who has ever worked for or watched CNN, Rosie O’Donnell, and hundreds of others. No matter the opponent, Trump’s fighting style remains the same. He always goes low once the fight starts, he will never admit defeat or apologize, and he uses these fights to distract from news that he doesn’t want to discuss.

While he’s operated this way dating back to his earliest public business feuds — his 1980s battles with the NFL, the mayor of New York, and the tenants in his buildings are among countless examples — this attacking posture has proved to be an effective strategy with his base. (Whether it’s effective with the overall public is very much up for debate.) A Gallup poll taken over the summer showed that Trump was the second most popular U.S. president ever among his own supporters, many of whom have been effusive about his willingness to take on these fights. While it may seem unpresidential to call a woman with whom you allegedly had an affair “horseface” on Twitter, the constant barrage of aggression has proved to be, at least in part, a savvy strategy. Trump’s base has said again and again that his untraditional political forcefulness is why they love him. Studies commissioned since the 2016 election have concluded that Trump’s support has increased in certain circles as a “cultural revolt against perceived communication restriction”; in other words, his popularity has grown as a revolt against political correctness. While undoubtedly true in certain cases, in others it’s simpler. His rude and vicious trolling is entertaining. If every figure in both parties operates with a certain sense of decorum, except for the one guy who decides to trash everything in his way, there will always be a group that sides with the latter. Trump’s shock value is a feature, not a bug. The angrier the rest of society gets about his antics, the more this group embraces them.

Tekashi has taken a similar napalm approach, with one significant difference: His fights get physical. Starting with Trippie Redd, the artist who gave him his start in the industry, Tekashi has squabbled with producers, gangbangers, radio hosts, and just about anybody else who gets in his path. He showed up at the Super Bowl, the most vanilla event on the planet, and became involved in a shoot-out with Minneapolis locals. He’s been in skirmishes in five-star hotels, at airports, in some of the fanciest restaurants in New York, while at a mall, at an $80 million mansion in Beverly Hills with Kanye West and many, many more. Many of these incidents have ended in gunfire.

Like Trump pettily exchanging barbs with Elizabeth Warren, Tekashi is strengthened by these feuds. Every step he walks in Los Angeles without YG or the Game stopping him is a net win for the people cheering him on from behind their keyboards. Speaking of keyboards …

The Internet

For a guy who has publicly admitted to never using a computer, there may be no politician who has ever been more effective at the internet than Trump. The power of his Twitter feed is self-explanatory: His unfiltered, often grammatically and factually incorrect thoughts are blasted to 56 million people in seconds, and the rest of the world soon after. While he hasn’t made significant inroads on any other social platforms, Trump understands and has said that he has the power to change international conversation with a 100-character blast. The other way that Trump has mastered the internet — in a way that’s harder to quantify but obvious to the millions who spend hours a day analyzing his every move — is by being incredibly effective at monopolizing the conversation. There’s really never been anything like it. The reach/stench of Trump has crept into our daily life. Internet media companies have been built over the last two years solely to cover, and in some cases to oppose, him. The media feeds itself on Trump content. He is, for better or worse — and it’s almost always worse — the most relevant person on the web.

While Tekashi’s reach is more limited, he is hurtling toward a similar level of influence there. Longstanding mainstream artists like 50 Cent and Kanye have realized the pop they get from being affiliated with him. Since he broke onto the scene, Tekashi has fully embraced his legion of die-hard followers as the only thing that matters, largely by way of the internet. He has broadcast most of his life on Instagram, which has helped him build an unrivaled following. By comparison, he has more followers on Instagram than J. Cole, Pusha-T, and Kendrick Lamar combined. His antics, as off-putting as they may be, are clinically designed for this moment. Is the average kid sitting at home more interested in reading about Kendrick’s writing process or Tekashi prancing through the streets of Chicago daring Gangster Disciples to shoot at him?

Besides his music videos, which routinely clock in at hundreds of millions of views on YouTube, Tekashi’s most viewed video on the platform is his infamous interview on The Breakfast Club. Before he joined the show, one that’s had no shortage of controversial guests, Tekashi boasted that he would be its most popular guest. Nine months and 16 million views later, he appears prophetic. Rewatching the interview now gives you a full view of both Tekashi’s many troubling flaws and his skill at confrontation. Going toe-to-toe with Charlamagne tha God, one of media’s most gifted interviewers, Tekashi bobs and weaves, answering nothing yet keeping the energy of the conversation up while simultaneously going on the offensive. It’s reminiscent of how Trump handles most of his non–Fox News interviews. He never stops moving, distracting, confusing.

Why do working-class voters support a president who has a golden throne in his mansion? Why is one of the most popular rappers way more interested in fighting other artists than writing or producing music? Both Tekashi and Trump, in their own ways, have figured out that chaos begets loyalty. The more intense the criticism, the more their fans surround and support them. Trump infamously but astutely said in 2016 that he could shoot somebody in the middle of Fifth Avenue and his fans would still support him. As we’ve seen from recent history, Tekashi and his friends have already tested this theory and gotten away with it.

On Monday, November 19, Tekashi was arrested with three of his associates on federal racketeering and firearms charges. The fallout from his arrest is unclear, but many legal experts have predicted jail time for the rapper. Tekashi would be far from the first major artist to serve time, but this predicament does offer one stark contrast between his antics and Trump’s. If Trump — like his former campaign manager, national security adviser, and lawyer — were to be indicted, legal scholars predict that he would be able to appeal the indictment all the way to the Supreme Court, where it would eventually get tossed. There is no precedent for a sitting president to be indicted, and that’s unlikely to change now. So for the time being, while Tekashi is facing legal consequences for his actions, his presidential counterpart is not. In America, not even all trolls are created equal.