The jeans were a mistake,” says Lawrence Lessig, the superstar Harvard Law professor. The jeans were a mistake because it’s pouring rain and freezing cold, and despite the best efforts of a billowing green parka his legs are now encased in wet black denim, with another few hours of slogging ahead of him. “I had snow pants,” he says. “I should have just worn them.”

It’s not like Lessig to go unprepared. As an early and fierce advocate of Internet freedoms, he gave TED talks before TED talks were a thing; his deployment of PowerPoint was so slick that an official Microsoft tutorial refers to “Lessig-style” presentations. But in his new incarnation as a champion of campaign-finance reform, the 52-year-old finds himself increasingly removed from his native, rarefied habitat. His latest gambit, and the reason he’s navigating an icy road in the wrong trousers, is the New Hampshire Rebellion, a 185-mile group walk that aims to make the issue the defining topic of the 2016 election.

Illustration by Simón Prades

During the run-up, Lessig promoted the Rebellion with a barrage of tweets, Tumblr posts, and old-fashioned mass e-mails. “I gather he’s doing some kind of march across New Hampshire,” the legal scholar and jurist Richard Posner told me when I called to talk about his former protégé. “So that sounds strenuous and time-consuming, right?” The whole journey will last two weeks and take Lessig and his compatriots across the state the long way. All of 50 hardy souls have joined him for the first leg.

When we set out from a park-n-ride just outside Dixville Notch, where the first ballots of the first primary are famously cast, the road conditions are terrifying enough that organizers hand out strap-on cleats and encourage us to pair up with walking buddies. (At a bar the night before, a man touted as the “leading logger in all the North Country” told us we were all “fucked.”) Our destination is a town called Errol, ten miles down the road. After we get there, the buddy system will remain in effect: At the motel, everyone but Lessig gets a roommate.

As we make our way down state Route 26, Lessig, the group’s nerd Pied Piper, sticks near the head of the pack, splitting off occasionally to walk alone. “People outside the system like us, we don’t have the resources or the power,” he had told the group during a morning pep talk, but to the extent that he is an outsider, he is a self-made one. After studying philosophy at Cambridge, Lessig pursued a career in legal academia that began with the clerkship with Posner and another with Justice Antonin Scalia. As a professor, he bounced from the University of Chicago Law School to Harvard to Stanford then back to Harvard. On the side, he led the movement to liberalize intellectual property online, co-founding the alternative copyright system Creative Commons. It made him a kind of Internet messiah.

“I’ve never been able to have a job that I feel I can do just that one job,” Lessig says. In his current crusade, that magpie nature has become a full-blown case of tactical ADD. Lessig believes that the corrupting influence of big money is the root cause of political stagnation, the “general problem” that thwarts progress on specific ones. But to him, it’s even direr than that: For the past year, he has been convinced that the existing system has blood on its hands. Lessig dedicated himself to campaign-finance reform at the behest of the late programming prodigy and Internet activist Aaron Swartz, who committed suicide while facing federal prosecution for liberating journal articles from an academic database—a prosecution that in Lessig’s view traces back to a “dumb law” that wouldn’t exist but for its deep-pocketed patrons.

And so, while the New Hampshire Rebellion is patterned after the exploits of “Granny D,” the octogenarian campaign-finance-reform activist who walked the length of country in 1999, Swartz is its real inspiration. Lessig sometimes calls the march “Aaron’s walk” and timed it to begin on the one-year anniversary of Swartz’s death. “That event radicalized me,” Lessig tells me. “It’s pushed me over an edge, a certain kind of edge.” One can’t help but worry what will happen should his efforts fail. For the sake of the country, OK, sure—but more urgently, for Lawrence Lessig himself.

Lessig helped make Swartz a weblegend by tapping the teenager to write Creative Commons’s code and touting his genius at every chance. But as he likes to tell it, it was Swartz who was his “mentor.” In 2006, while both were attending a conference in Berlin, Swartz convinced Lessig to switch fields over the course of a single conversation. “This Cato guy tweeted today that there’s no connection between Aaron and this issue, and that it was terrible that I was trying to link them,” Lessig tells me as we trudge along. “And I said, ‘It wasn’t my issue—it’s his issue! He’s the one who made me do it!’ ” At the end of the first leg, Lessig had planned to show the marchers a documentary about Swartz. Alas, he left the projector behind.

In 2008, Lessig created a nonprofit called Change Congress with the political consultant Joe Trippi. He began calling for a second constitutional convention and flirted with a congressional run. By 2012, he had perfected another PowerPoint presentation and published two books on the topic. Finally, disillusioned with his old U. of Chicago colleague Barack Obama, Lessig became an adviser to former Republican governor and 2012 presidential candidate Buddy Roemer, who was funding his campaign exclusively through small donations. “I just don’t think [Obama] has the strong character to push something like this,” he says.

Certainly, Lessig has broadened the campaign-finance-reform movement’s tent. The marchers I meet on the first weekend of the walk are largely of the liberaltarian variety, equal parts Reddit and “Portlandia.” A jewelry designer from Vermont called Bill Butler gives me a jar of his campaign-finance-reform fudge sauce, “Amendmint.” My bunkmate is a retired ophthalmologist from Alaska called Robert who has affixed to his backpack a poster of Swartz’s face transposed over the image of a Q.R. code. Another, even more fervent Swartz acolyte has a habit of wandering into the middle of the road to wave at oncoming cars. One confused driver stops to ask whether we need assistance.

For the duration of the four-hour trek, we progress more or less single file down the left shoulder of the highway, scurrying out of danger whenever a plow truck materializes. Lessig passes some of the time collecting beer and soda cans that litter the roadside. Under his coat, he has on a black t-shirt bearing Swartz’s name in lowercase white letters. “I’ve never known a loss remotely close to that,” he’d told the group during breakfast, choking up. “Not just because I loved him, but because I feel like we could have done more. As I love my country, [I] don’t want to feel like we could have done more. So we start today, remembering those people we’ve let down.”

At the end of the day, the group stops for dinner at a restaurant called Northern Exposure, where on the menu an illustrated moose flashes diners as they contemplate their orders. Rick Hubbard, an older marcher who once pursued a long-shot U.S. Senate bid in Vermont, asks Lessig how his Harvard Law colleagues feel about his activism. “I don’t know,” Lessig responds. “You don’t ask?” Rick says. Lessig shakes his head. Earlier, he had told me, “I don’t have a lot of friends in my field.” Instead, he has aligned himself with the likes of Roemer and Congressman John Sarbanes and the media personality Cenk Uygur, all of whom are scheduled to join the march’s final stages.

Meanwhile, a French reporter who has embedded with the rebellion for a few days will bring its message to Le Monde. A pair of videographers on the trip have been discussing the possibility of a documentary with An Inconvenient Truth director Davis Guggenheim. There is another march planned for next year and yet another for 2016. Momentum, of a sort. And yet, Lessig is not quite ready to give up his establishment perch entirely. Our conversation turns to Bill McKibben, the New Yorker writer-turned-environmentalist, and Lessig’s mood flattens. “He’s braver,” he says. “He gave it up.” Lessig, for his part, was still teaching Contracts last semester.

In 2007, when Lessig formally announced his new cause to a room full of surprised tech acolytes at something called the iCommons iSummit, he called it a ten-year project, just as his copyright fight had been. As we approach our stopping point in Errol, New Hampshire, I ask Lessig what he’ll do if, by the end of that timetable, he hasn’t managed to change campaign finance at all.

“It’s the most obvious, likely outcome,” he says, after a few seconds. “And I’ve literally never thought of that.”

Simon van Zuylen-Wood is a staff writer at Philadelphia Magazine.

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