One night last summer, Luis Calderin, a nightclub DJ and one-time lifestyle branding guy for a snowboarding company, found himself across the table from Senator Bernie Sanders chatting about various hip-hop artists.
The pair were dining at a farm-to-table restaurant in Portland, Maine called Local 181, which Calderin remembered thinking the senator picked "because it sounded like a local union chapter."
They were tossing around ideas about Calderin's future role as the presidential candidate's arts, culture and youth vote manager, when the subject of Michael Render, known by his stage name Killer Mike, came up. Seven days earlier, Render had independently tweeted his support for Sanders based on his call to restore the Voting Rights Act, and the senator wasn't sure whether to reach out or let the endorsement slide.
"Is this Killer Mike good?" Sanders asked.
"Yeah," Calderin replied. "That's a very strong endorsement."
So began the conversation that would lead to one of the oddest political pairings — outwardly at least — of this election cycle; and one that would significantly jack up Sanders's street cred with young voters. At Calderin's initial urging, the campaign set up a meeting with Render, who later went on to stump for the senator in states across the US, including the rapper's home town of Atlanta, Georgia, where the men were famously photographed lunching at the Busy Bee Cafe. Calderin would later introduce Sanders to some 300 more celebrity surrogates, including the likes of Diplo and Aoki (whom he labelled the DJ versions of "this generation's Rolling Stones"), the Red Hot Chili Peppers, Lil B, and comedians like Seth McFarland and Sarah Silverman.
Calderin, a youthful 41-year-old who often sports a wide-brim fedora and black wayfarers on the campaign trail, is the man who now wrangles their schedules. He is one part of a campaign that has looked to move away from a typical establishment-type operation and hire a diverse crew that now includes Mel Sandico, the campaign's in-house DJ who spins tracks at official events; Arun Chaudhary, Sanders' digital creative director and formerly the White House's first official videographer; and Marcus Ferrell, the campaign's director of African American outreach and a self-identified hip-hop enthusiast who engaged in a freestyle battle with surrogates in a campaign hotel suite on the night of the Iowa caucuses.
"The people that we have on board are not traditional political folks," Calderin said. "[As] I learn more about their personal stories, it makes sense that a guy like myself — who came in as a hip-hop DJ and worked at a snowboard company — would be the right guy for [this] political movement."
Having never worked on a political campaign, Calderin seemingly walked into one of the toughest gigs in marketing: cultivating youth excitement for a 74-year-old senator, who barks repetitively and almost exclusively about economic and social policy. Last year millennials surpassed baby boomers to become America's largest voting bloc, but they are also one of most notoriously unreliable and apathetic voting demographics in the country. Yet, the campaign has found its biggest successes with 18-34-year-olds, who have become transfixed by the senator's unlikely appeal. After all, Sanders, a grandfather of seven whose hair was already graying before millennials were born, recently asked a crowd in Nevada whether the word "hip" was still in use.
"It doesn't make any sense from a traditional marketing strategy or standpoint," said Calderin. "But I think we are doing things differently and that is what is needed. I think that's the whole point of this campaign — not to follow the status quo."
Before Sanders became his boss, Calderin knew him as the mayor of Burlington and step-dad to his best friend, Dave Driscoll. Calderin, the son of Cuban immigrants and now father of two, moved from Florida to the Vermont city of roughly 42,000 people in the mid-80s, when he was a teen and still heavily influenced by hip-hop groups like Public Enemy, De La Soul, and Boogie Down Productions. He grew up skateboarding with Driscoll and regularly saw Sanders and his wife, Jane, in the neighborhood grocery store and driving their Chevy Volt around town.
Despite his familiarity with the family, Calderin still calls Sanders "senator." It's one measure of the way in which the Sanders team is still flavored by the convention and formality of Washington DC politics. But the campaign has also sought to abandon convention, especially in actively seeking fresh blood, like Calderin, a prolific Instagrammer who says he spent his childhood and early teens as a b-boy in Miami.
Before he signed onto the campaign eight months ago, Calderin was a brand manager at Burton Snowboards, where he worked alongside Driscoll. At the same time, Calderin also moonlighted as a DJ in bistros and nightclubs, playing wildly eclectic sets that included anything from trap remixes to Top 40 tracks and deep house club anthems.
One lunchtime, Driscoll and Calderin talked about potential songs for the campaign's official playlist. Weeks later, Calderin was having dinner with Sanders in Portland, Maine, following one of the biggest presidential candidate rallies the town had hosted in 25 years. Nearly 9,000 of Portland's 66,000 residents packed the concert venue that night.
Calderin hadn't yet officially joined the campaign. He wanted to see what was happening on the ground and "get a feel for what a rally was even about" before he signed on.
"When we got down [to the rally], we were both kind of wide-eyed," Calderin recalled. "There were so many people lined up, and guys selling buttons and t-shirts, and it sort of instantly reminded me of a concert for a band."
But unlike a band, "there weren't any bells or whistles, no laser shows, no choreographed anything, just a man on the stage talking the truth," he added.
"I turned to Dave and said 'I think your dad is blowing up. This is really happening right now.'"
From there the senator's following grew rapidly. Within a matter of weeks, hundreds of memes on the man and message spread online, while small donations to the campaign — which are now close to reaching a record 5 million — poured in. Results soon showed the candidate had gained the support of more than 80 percent of voters under 30 in early states like Iowa, New Hampshire, and Nevada, where tens of thousands of people filled rally venues, where they screamed out lines from Sanders's well-worn stump speech.
Despite the campaign's rapid growth, Calderin describes it as "still very much a grassroots organization."
When he started with the campaign eight months ago, Calderin's job was to help Sanders court the youth vote, but his unscripted role has been rewritten, largely by himself, and now he's actively pursuing cultural leaders across all ages and demographics. That kind of shifting of roles and adaptation of staff, especially those from outside the political sphere, has allowed Sanders' team to adjust to his rapidly expanding campaign over the last year.
Now Director of Arts and Culture, Calderin has helped hook the campaign up with the likes of entertainer Harry Belafonte, activist and author Dr. Cornel West and actress Susan Sarandon, who have been let loose to stump solo and do press junkets for Sanders. Trusted surrogates like Sarandon help spread the senator's message across the country, especially when multiple primaries are crammed within hours of each other and Sanders can't physically appear in each state that is voting. After every win or loss, the campaign has to recalibrate and "identify which markets we're going to activate again," Calderin said, meaning the states they plan to send surrogates to next.
Words like "activate," "targeted" and "key markets" sometimes pop out of Calderin's mouth – evidence of his job in marketing and branding for Burton Snowboards. But from the onset, Sanders had instructed Calderin to sweep branding tactics aside, and stick to the issues.
"He said 'Look, I want to be very clear — I don't need any marketing, don't market me or brand me as anything. This isn't about me, this is about the movement'," Calderin recalled the senator telling him over dinner. "That's been the campaign's guiding mandate the whole time, and that is really what young people have gravitated towards. I think they sense his honesty and they are passionate about these issues."
Some surrogates have shared a similar sentiment. Actor Josh Hutcherson, 23, who is best known for his role as Peeta Mellark in The Hunger Games and campaigned for Sanders in Iowa, believes "there is a misconception [in the media] with the youth vote."
"Many people are attributing their vote to wanting free college or jumping on the young band wagon or something, but it's not that," Hutcherson said. "They have a candidate that is finally talking straight. ... He doesn't dance around issues or try to muddy things up with political rhetoric."
Hutcherson became involved with the campaign through his friend Mark Foster, the frontman for the indie pop band Foster the People. Both stumped at massive rallies for Sanders in Iowa last month.
For some surrogates, 2016 was the first time they'd heard about Sanders. But for others, the senator is a well-known figure who has been pushing the same ideals for decades. Every celebrity has had "different points of entry," Calderin said.
"If you are politically aware and a progressive and you live on the East Coast, you know who Bernie Sanders is because he has been saying the exact same thing since the 60's," said actress Gaby Hoffman, who has been on the campaign trail in between shoots for the Amazon series Transparent and looking after her 15-month-old daughter.
Hoffman became emotional to the point of tears as she described landing in Iowa for the first time and meeting supporters who were talking about the issues that kept her up late at night and that she talks about at home with her boyfriend.
"It was honestly like a real balm from my soul it was a huge release," Hoffman said.
This election cycle, the campaign has also mounted a social media operation this that has built on Barack Obama's use of Facebook to mobilize voters in 2008. Twitter especially has been a hub where the campaign has been successful in connecting with artists to bring them on board. Killer Mike, who first came across Sanders while "smoking a joint and reading his tweets," was among dozens whose first contact with the campaign was made in 140 characters or less.
"We obviously monitor anytime anyone says anything about the senator on social media," Calderin said. "So we've had a number of people come in that way, on their own organically; either retweeting us or making statements, or coming out with endorsements of their own and we just follow up from there."
Of the hundreds of celebrity surrogates Calderin has managed for Sanders, he's lost just one. Calderin said he had no idea why on the morning of the Nevada caucuses comedian Will Ferrell abruptly cut off his months-long support for Sanders and switched to field for Hillary Clinton. The defection surprised a lot of people and made national news, but Calderin didn't seem fazed, spinning it as an effective development for democracy.
"For us, as long as people are engaged in the political process in any way, that's a win. We want people to be involved. Americans for so long have just tuned it all out," Calderin said. "So even that [incident] turned into a positive, where people became conscious of one of their favorite comedians and actors making a move like that, which created a conversation about the caucuses."
Follow Liz Fields on Twitter: @lianzifields