Uganda’s Reggae Star Turned Politician Bobi Wine Puts His Future on the Line for a Shot at the Presidency

To find the most famous musician in Uganda, simply punch his name into uber.

If you follow directions to Bobi Wine Residence or Bobi Wine Road, you’ll eventually find yourself on a rutted mud track that winds through the remnants of an old banana plantation on the fringes of the Ugandan capital, Kampala. When TIME visits in September 2019, the man himself greets us at his front door. He is wearing boxing gloves.

Out of breath and sweating, Uganda’s most unlikely presidential candidate proffers a fist bump and apologizes for a training session gone long. “I’m getting ready for Museveni,” Wine jokes, referring to the country’s current President. A onetime guerrilla leader, Yoweri Museveni has ruled the nation for more than three decades through a combination of deft politicking, questionable election practices and a ruthless use of force. Having done away with constitutionally mandated term limits and presidential age caps, the 76-year-old could conceivably rule for the rest of his life in a country where the vast majority of the population has known no other leader.

Now 38, Wine, an up-from-the-slums reggae sensation and political newcomer, is taking him on in the presidential election due to take place on Jan. 14. “The old man has been in power long enough,” says Wine, who blames the President for the fact that more than 80% of Ugandans between 15 and 29 work informally, with little to no income, and no job security. “We are the generation that was created by Museveni’s failures,” says Wine, who was 3 years old when his rival first took power. “Poverty, no chance for a good education, growing up in the ghettos with no opportunities–this is all due to the lack of leadership and investment in our youth. Museveni’s corruption is destroying our country’s future.”

Yet no matter how accurate the diagnosis, or how well received his message, Wine’s quixotic campaign for the presidency of Uganda is a long shot, says Aili Mari Tripp, a professor of political science at the University of Wisconsin and author of Museveni’s Uganda: Paradoxes of Power in a Hybrid Regime. “The playing field is not level, making it nearly impossible for any other candidate to win, no matter how popular.” If anything, the upcoming election is a test of the limits of populism when stacked against the entrenched powers of dictatorship, cloaked in a facade of democracy.

As a musician, Wine can and does boast a massive following–calling him Uganda’s answer to Jay-Z, he says rakishly, “is maybe understating it”–but as he attempts to translate that pop stardom into political power, he is putting himself in the ring with one of Africa’s most wily leaders, in a nation where opposition politicians routinely risk jail, beatings and the occasional sudden and mysterious death. Even if Wine succeeds with his goal of creating a popular movement strong enough to unseat Museveni, he himself may not survive the process. “Museveni isn’t going to hand over power on a silver platter to anyone,” warns Helen Epstein, a professor of human rights at Bard College and the author of Another Fine Mess: America, Uganda and the War on Terror. “Uganda really is one of the most repressive countries in the world.”

Which is why Wine is subjecting himself to a punishing bout of training with one of the nation’s best boxers. As Wine ducks and jabs on the driveway of his stately colonnaded home, the coach urges him through “one more round” six more times. Finally, Wine–wiry, heavily tattooed, and clad in black tracksuit pants and a sweat-drenched T-shirt–collapses to the curb. “I don’t intend to beat nobody,” he says. “I’m making my body resistant to beating, to make sure I don’t get so bruised when I take the blows.”

It is wisdom born from experience. In August 2018, Wine was at a parliamentary campaign rally that turned violent. People started throwing stones, and government security forces opened fire, killing his driver. Wine was imprisoned, badly beaten and charged with treason. When TIME met him, Wine predicted things would get worse as the elections drew near: “The more scared the old man gets, the more he will lash out. People are going to be hurt, supporters will be targeted, people will be killed.”

His words began to sound less like paranoia than like prophecy, on Nov. 18. After he was arrested by police for the second time in a month, his supporters set up a blockade and confronted police on the streets of Kampala. In the ensuing clashes, at least three people were killed and 38 injured. As TIME went to press, Wine was still in detention, leaving only a message to followers on his Twitter feed: “The price of freedom is high but we shall certainly overcome.”

Born Robert Kyagulanyi Ssentamu to a onetime political family driven to penury for backing the wrong candidate, Wine was raised to avoid politics. He gravitated to music from a young age and began recording and performing sold-out concerts while an arts student at Kampala’s prestigious Makerere University. His stage name is an homage to two of his musical idols, Bob Marley and Bobby Brown, and he chose Wine, he says, because “I realized I was only getting better with age.” He was 22 at the time.

While his early works were influenced by the weed and so-called ghetto-life swagger of late-’90s hip-hop (including virulently homophobic refrains that reflect widespread Ugandan prejudices), by 2010, he had started infusing his rollicking reggae beats with socially conscious messaging. In 2014, he was invited to tour in the U.K., but his visa was denied after human-rights groups protested his earlier homophobic lyrics. It was, he says, “a humbling moment. I realize now I should have been more tolerant and respectful to people that are different from me.” Wine retracted his statements and apologized to Uganda’s LGBT community, many of whom now back him. “He really has transformed,” says Ambrose Barigye, an LGBT activist who fled Uganda in 2018 but who still follows the movement closely from exile. “Now the government is using it against him as propaganda, saying he is funded by the gay West,” says Barigye.

In 2017, a parliamentarian in Wine’s district stood down, and Wine saw an opportunity to amplify his call for social change by running for the seat. He won the election with 78% of the vote, despite the fact that he had no party and knew nothing about campaigning. He has since successfully campaigned for several other opposition candidates, subbing in star power where the substantial funds normally needed to win elections did not suffice. But his fame, onstage charisma and infectious songs laced with antigovernment slogans proved too threatening to the country’s leadership. The government has banned his performances onstage and on air since 2018, depriving him of both a platform and an income. Figuring he had nothing left to lose, Wine decided to run against Museveni. “They weren’t letting me be a musician, so I thought I might as well become a President,” he says.

If elections in Uganda were based purely on popularity, he could yet succeed. Wine’s campaign channels the frustration of the country’s youth–78% of citizens are under the age of 30–and of Uganda’s impoverished classes, who make up more than one-third of the population. The COVID-19 pandemic has only exacerbated the nation’s economic inequalities, with 2020’s GDP growth projected between 0.4% and 1.7%, compared with 5.6% in 2019. When Wine first started using his music to call for social justice, Museveni disparaged him as a “ghetto President.” The name stuck. Supporters already address the singer as President, and ghetto has become a badge of pride not just for those who emerged from the same urban slum as Wine, but also for the underserved and ignored in a country where political power is more likely to enrich the powerful than improve the lives of anyone else. Vanity plates on Wine’s Cadillac Escalade read ghetto. Now that the sobriquet has expanded to include most Ugandans, the joke is on Museveni, says Atusingwize Jonan, a young presenter for the privately owned digital-media company Ghetto TV. “This is a guy who came from us, so he speaks for us. He knows what we all go through.”

You only need to accompany Wine on a drive through the streets of Kampala to see how fervent his supporters are. Local residents holler his name. Old ladies on the back of motorcycle taxis cheer and wave. Shopkeepers raise clenched fists in solidarity. “People power!” Wine shouts. “Our power,” they respond, completing his movement’s name and slogan. Supporters drop 10,000- or 50,000-shilling ($3 or $15) notes through his open window, symbolic sums in a country where politicians often pay that much to get citizens to attend their rallies or, in some cases, vote for them.

Wine’s face is instantly recognizable; so too is his movement’s trademark red beret, with its logo of a raised black fist. He favors the slim black trousers, batik shirts and dark-framed glasses of the international revolutionary intellectual. His bookshelves are lined with the biographies and manifestos of the world’s liberation leaders, from Malcolm X to Che Guevara, Nelson Mandela and Martin Luther King Jr. When he speaks, it’s clear he has digested them all, unconsciously regurgitating quotes from Bishop Desmond Tutu, Barack Obama or Malcolm X, sometimes in the same sentence.

The revolutionary rhetoric and pageantry appeal to a nation desperate for change, but they mask his campaign’s hollow core. Wine is pushing for transformation, yet he has no platform, and bristles when asked about his policy plans. What he offers instead, he says, is a vision of what Uganda should be: “A country where there is no impunity. Where we are all equal before the law. Where everybody has opportunity regardless of their tribe or sect or background. Where institutions are supreme and respected.”

The point is not that Wine wants to be President–he says he doesn’t–but that the current President needs to go, and so far, no one else has been able to unseat him. “I look at myself as the most unqualified person for the role of President,” Wine tells TIME over a lunch of tripe stew at a Kampala restaurant popular with government officials. “But God does not take the qualified; he qualifies the chosen one. What God has graced me with is the ability to rally Ugandans to own their own country. If we can do that, all I will need to do is be a good manager.”

There are a few major obstacles to overcome first. Wine still faces charges of treason dating to the violent rally in August 2018, when his supporters allegedly threw stones at a government convoy, and he could be called to court at any time. (He denies the charge and says it is politically motivated.) Last year, the government banned civilian use of the red beret worn by members of Wine’s People Power movement. In July, Uganda’s Electoral Commission, while officially independent, refused to register Wine’s movement as a political party–an essential designation for contesting elections.

Wine circumvented the ruling by aligning with a small established party that had already registered. Then the party voted to change its name, and elected him as leader. “As soon as the President learned I had managed to register a political party despite his best efforts, he fired the top officials of the Electoral Commission,” Wine cackles over the telephone in early October. “I ducked his punch, and punched back harder.” Museveni said on Twitter that the officials were fired because of “corruption.” (Despite several requests, Museveni’s office declined to speak with TIME on the issue of Wine’s campaign or the upcoming elections.)

And as elections approach, there are signs that Museveni may be preparing for further crackdowns. Citing the risk of COVID-19, the Electoral Commission has prohibited public rallies in favor of TV and radio campaigning. Yet few TV and radio stations will host Wine, for fear of contravening a long-standing ban. When he does manage to make an appearance, the broadcasting station is usually raided within moments.

Wine’s biggest fear, however, is an assassination attempt. In order to make sure his meal of tripe stew would not be poisoned, Wine had sent a couple of staffers to the restaurant to order, while he idled in his car around the corner. As soon as the food arrived, the staffers called him, and only then did he and his entourage come in to take their places around the table. “Museveni will use every trick in the book to make sure I am not a threat during the elections,” says Wine. So why does he risk eating in a pro-government venue? Wine grins mischievously and jerks his chin at a nearby table, where a couple of government officials are hastily abandoning a half-completed meal in an effort to avoid being seen in the same restaurant as Museveni’s rival. Everyone else clamors for selfies. Wine takes his victories where he can find them.

Many Ugandans expect that the election will be rigged, but even without interference, Museveni would be tough to beat. After helping oust the military despot Idi Amin and overthrowing his successor, Museveni came to power in 1986 promising democracy, the elimination of corruption and an end to inequality. At the time, he was celebrated by the West as part of a new generation of African leaders, and he still enjoys significant popular support despite his antidemocratic tendencies. He belongs to the more modern iteration of strongman, keeping himself in power (and compensated well for it) while also bringing in just enough reforms and investment to ensure a placid population. Though most Ugandans agree that it is time for a change in leadership, the urban elite who have managed to build a stable life despite, or even because of, the ruling party’s deeply entrenched patronage networks fear disruption. “Museveni is a dictator, and it’s not right how he is staying in power. But I would rather have Museveni and be safe and stable than risk the chaos of Bobi Wine,” says 26-year-old interior designer Patricia. (Like most Ugandans fearful of speaking against the President, she asked to use only her first name.)

And while corruption is rampant, it has trickled down so far that no one entity can be punished at the polls for the country’s dysfunction. Few politicians are trusted, whether in government or the opposition. The cynicism is fed by a wildly partisan press that only gets called to account when it impugns government officials. As a result, most Ugandans have given up any expectation of good leadership, says Simon Osborn, a consultant formerly of the National Democratic Institute (NDI), a Washington, D.C.–based NGO.

Largely because of the efforts of organizations like the NDI, some tactics of electoral manipulation have ended, says Osborn, who is now a technical adviser to the E.U. delegation in Uganda. That doesn’t mean the vote reflects the true will of the people, he cautions. “The days of ballot-box stuffing and violence at the polls are largely over. The alternative is money. And so far, that seems to work.”

Ugandans call it the commercialization of politics, where voting is a transaction, not a choice. “Increasingly more and more people are expecting to be paid to go to rallies, to vote, and to vote accordingly,” says Osborn. “And Bobi doesn’t have the money to do that.”

Not all of Uganda’s young voters are convinced that Wine is up to the challenge of leading the country in a new direction. Samantha, a 22-year-old university student, acknowledges that Wine is a powerful voice for Uganda’s disadvantaged youth, “but not all of us are in that category.” Just because Wine’s music was the soundtrack to her childhood doesn’t mean he would be a good President, she says. “He shaved his dreadlocks, but we still know him as the reggae musician, the weed smoker. Can we trust him?”

Wine dismisses the criticism as government propaganda designed to discredit his campaign among the nation’s elite and conservative classes. He is fighting for accountable leadership to benefit all Ugandans, he says. “This is about all of us, the young, the professionals, the lawyers, the doctors, my auntie who lives in the village, the young man that drives a boda boda [motorcycle taxi]. If we unite to save the country, it will be for all of us.” And despite the throngs of supporters who descend upon his car at intersections, the proliferation of T-shirts proclaiming In Bobi We Trust and the ecstatic crowds at his political rallies, Wine wants it known that the campaign is not about him; it is about change. “If we make it about me, Museveni would only have to eliminate me, imprison me, to bring the revolution to an end.”

Wine has everything he ever dreamed of as a kid growing up in the slums of Kampala: a brilliant wife who is a celebrity in her own right, four kids, riches from his career in music, fame, respect and the adulation of the entire country. Why is he risking it all on a quixotic campaign that already nearly took his life? “You mean, why don’t I just let the voiceless Ugandans die, why don’t I just let them suffer?” he volleys back, waving his boxing-gloved fist to take in the manicured lawn, the Escalade parked behind him, his new Nikes. “Look at the car I drive, look at the glamour I live in. I am all this and more because Uganda loved me. So I can’t let Ugandans down now. I can’t let them suffer in silence when I have the loudest voice.” He jumps to his feet and launches into full campaign mode. “This is a campaign to put an end to dictatorship, and we are either going to succeed or die trying.” Pacing and speechifying before an audience of one, Wine sounds like he’s issuing less a prediction than a dare. He pulls off his gloves and goes inside to freshen up for the battle to come.

–With reporting by MADELINE ROACHE/LONDON