With 14 candidates on the ballot for the city’s Feb. 26 mayoral election, it can feel tempting to turn an apathetic eye on the whole race. There’s too much information to sift through, and politics in Chicago are hopelessly corrupt anyway, right?
Sean Raju disagrees. He’s determined to show other Chicagoans why the election matters.
He’s the filmmaker behind the web series “Chicago’s New Boss“, which sets out to demystify the snaking trail and loaded history of Chicago politics in order to prep voters for the upcoming election. His videos call out issues that the typical voter may not understand or have time to unpack—like the implications of a candidate not disclosing his or her tax returns.
“There’s such a huge history associated with Chicago politics,” Raju said. “If you try to jump into it, it can get really overwhelming really quick.” His videos are especially designed for young people who may be tackling the city’s politics for the first time, though they also have appeal for the masses.
Through humor and robust reporting, Raju both clarifies political complexities and debunks longstanding conventions. One of his videos demanded tax return transparency from the candidates, some of whom have yet to release their tax returns. He has talked about the rigged voting system and those working to break it.
He has also profiled frontrunners Toni Preckwinkle and Susana Mendoza to break down their extensive political careers and plans on future videos to feature lesser known but fully capable candidates, such Logan Square resident Lori Lightfoot, who we profiled last year. Another video will target the aldermanic elections.
Raju’s personal political views are progressive, which he freely admits to his viewers. He encourages his audience to decide for themselves where they fall on different issues, and to question his facts if they see any inaccuracies. “Hold me accountable!” he proclaims at the beginning of his Susana Mendoza video.
He previously served as a video producer on the campaigns of progressive politicians Daniel Biss, who made an unsuccessful run for Illinois governor last year, and Senator Elizabeth Warren, the Massachusetts Democrat who recently entered the 2020 presidential race.
“I was lucky enough to work with two people who are honest, good and fight for the regular people,” he said. “In a world where we’re so disenchanted with politicians, I saw there are people who are doing good and that gave me hope.”
Throughout his time filming Warren’s campaign videos in Boston, he was keeping an eye on the Chicago mayoral landscape. When Rahm Emanuel announced in September that he wouldn’t seek reelection, Raju knew he wanted to come back to create “Chicago’s New Boss.”
“I think this is a watershed moment for Chicago,” he said, noting that this is only the third Chicago mayoral election in 80 years without an incumbent on the ballot. “If there’s any way I can tell the story and make average people more aware of what’s going on, I think that would be a really incredible experience.”
Politics for the Not-So Political Person
Raised in California’s Bay Area, Raju first came to Chicago to study film at the University of Chicago. Back then, he wasn’t anticipating delving into politics.
“I viewed politics as a sport—I definitely paid attention to presidential races, but not in a way that I really thought it was going to impact regular peoples’ lives,” he explained. “I think it was easy to be lulled into this false belief that politics isn’t something a regular person can engage with.”
But after the 2016 presidential election, Raju decided he wanted to use filmmaking to tell stories that “inform, educate and uplift” the public as a way to give back. He thinks the city’s corruption can silence the public and wants to show ordinary people that they have a voice—and a stake—in local politics.
“[Machine politics] want you to feel like you can’t make a difference. And if you become jaded, they’ve won,” he said.
He’s now targeting the audience that he used to belong to, which makes it easier for him to both sympathize with and call them to action.
“I think a benefit of being someone who hasn’t been political his entire life is that I know what it’s like to feel disenchanted, to feel like my voice doesn’t matter. That is a very recent feeling for me,” Raju said.
While Raju films and edits his videos all on his own, he calls on friends to help him fact-check and give their perspectives. Former Logan Square resident Hussien Salama, who worked with Raju on the Biss campaign and has since produced videos for the Democratic Congressional Campaign Committee, advises him on audience development.
“Sean is not trying to divorce his own personal political interests from the series,” Salama said. “He’s trying to be a person talking about things.”
Raju’s “normal person” image also helps him strike a lighthearted and relatable note throughout the series, as evidenced in an outtake where he takes a magnificent tumble during a poignant lakefront scene.
“Things in Chicago sometimes feel so backwards that the best way to have people sympathize with what’s going on is to realize this is ridiculous. And it’s so ridiculous it’s kind of funny,” Raju said. “I don’t want to ever make light of serious issues. I want to call out the absurdity that is Chicago politics.”
“Chicago’s New Boss” is an entirely independent venture, for which Raju is not getting paid.
“He’s literally a lone guy trying to make content that he cares about and actually inform people. It’s a task,” Salama said. “And what he’s been able to do so far in just a couple months is astounding.”
While Raju’s early videos received about one thousand views each, his sixth video, entitled “Release the TAX RETURNS!” been viewed 12,000 times. His tenacity is a reflection of Chicago itself, which he said has given him a sense of community that other cities haven’t.
“There’s a resilience in the Chicago character. No matter how cold the winters get, no matter how corrupt our politicians are, no matter how bad our sports teams are, no matter how bad life can get, we’re still hopeful,” Raju said. “We’re still fighters.”
Featured photo: Sean Raju creates new Chicago’s New Boss videos about once or twice to tackle different aspects of the upcoming mayoral election. Photo courtesy of Sean Raju.