When Robert Kyagulanyi Ssentamu released Akagoma, a song that thrust him into music stardom, very few people knew that the self-styled "Ghetto President" harboured political ambitions.

Yet a close look at the musical foundation that the man, who is best known by his music stage name, Bobi Wine, had built, political undertones were written all over for anyone who cared to study the character of the Makerere University diploma graduate of Music, Dance and Drama, to notice.



For instance, as his colleagues within the same music ilk of the time, Bebe Cool and Jose Chameleone, rushed to Kenya to find a footing under the guidance of the Ogopa Deejays crew, Kyagulanyi decided to stay in Uganda.

Ghetto days

He formed the Fire Base Crew in Kamwokya, an area he named Uganja land. It is through these ghetto hallmarks of the Kamwokya territory that Bobi Wine honed his musical skills to perfection and later named himself the president of the lowly area that was largely dominated by destitute and impoverished youth, who saw him as a symbol of hope.

Indeed, for the past half-decade, he has been one of the most consequential people in the country's musical world. However, it was not enough for him to just bask in the glory of a towering musical career. He saw something great emerging in the country- the youthful population that needed a voice.

"This is not a political game; this is a leadership game, a war between the people of Kyadondo and ignorance, poverty and disease. This is not a contest of personalities, today is the first step in getting all of us together to address our challenges," he said shortly after he was nominated to contest as MP for the Kyadondo East parliamentary byelection in 2017.

Tight rope

To him, the goal was to figure out how to tap into this wave of determined and no-holds-barred crop of youth, who, according to the recent population figures, constitute 73% of the country's 38 million people.

However, like a person travelling on dangerous slope, Kyagulanyi's venture into politics was as slow as a snail, and could easily go unnoticed by someone, who is not a keen observer of the political landscape.

Punctuating his songs with lines scripted to shine a torch on the social malaise afflicting people in the country was one of the strategies he employed. The ghetto president's other strategy was to build close ties with Mengo, the seat of Buganda government and also work closely with opposition political heavyweights, especially Forum for Democratic Change party kingpin Dr Kizza Besigye.

Besigye-Mengo links

To showcase his unwavering loyalty to Mengo and Kabaka Ronald Muwenda Mutebi, he coined another name for himself, Omubanda Wa Kabaka.

Poverty, poor living conditions, social injustice, Police brutality and other social problems were some of the issues that the man, who until recently used to have trademark dreadlocks, used to tackle in his music, especially songs, such as Kiwani and Ekikomando.

Tackling politics, especially by speaking truth to power in songs, such as Situka, Dembe and Akalulu, challenging the status quo, participating in fundraising drives and donating to society, were some of the other activities that Bobi Wine undertook, especially in the post-2011 general elections, perhaps in preparation for his grand entry into politics.

"From now on, I will be a man of immense responsibility. After marriage, I will not be involved in childish things," Bobi Wine said, shortly after wedding his longtime friend, Barbra Itungo, in 2011.

In fact, Itungo told supporters during one of the rallies that Bobi Wine has always been a leader, who balances entertainment with several activities - sometimes venturing into commercial projects, farming. property development, among other things.

A family man, who is largely respected for managing well the transition from a typical raga-muffin, who at one time confessed that he smoked weed, to a leader positioning himself to uplift his community to emulate his story of from rags to riches, Bobi Wine's political life has surprised many.

For example, during the final lap of Kyadondo East byelection campaigns, social media commentators said the political novice had pulled off one of the largest rallies of the day. despite the fact that he was campaigning in Besigye's home area. Besigye campaigned for FDC candidate Apollo Kantinti, while President Yoweri Museveni combed Kyadondo East for NRM's Sitenda Ssebalu.

People's voice

To some observers, by pulling off such huge rallies, Bobi Wine showed that he had pumped into the old-style political jostle characterised by the NRM-FDC battle, fresh air.

At 43 years, Bobi Wine represents a new crop of leaders who not only resonate with the challenges of the day, but also fall under the youthful populace that wants to take charge of their affairs.

To many observers, Bobi Wine's shrewdness was had exhibited when he bruising run-ins with the establishment and Mengo relationship with the Besigye- FDC camp, two crucial movers that Bobi Wine had built his political career on.

In 2017, Bobi Wine was publicly involved in a public feud with Nkuluze Trust (Mengo's Royal Treasury) over land. Nkuluze demolished a parking facility and road leading to his One Love Beach in Busaabala, Wakiso district, claiming that the musician turned politician had illegally occupied the land. Despite the public feud, Bobi Wine was careful not to attack Mengo head-on, instead choosing to pinpoint a few self-seekers in Mengo.

When Besigye opted to comply with the FDC party and decided not to support him, Bobi Wine did not take offence. One of Kyagulanyi's campaign messages was, "despite the fact that Besigye is a friendly force, he cannot be here with us because of party principles, but he has said publicly that he will be happy if 'Bobi Wine' wins".

A son of a DP stalwart, Jackson Wellington Ssentamu (RIP) of Kanoni Gomba, and young brother of Eddie Yawe, who unsuccessfully contested on a DP ticket, Bobi Wine is not entirely new to politics. At a 2017 political rally in Gayaza, Bobi Wine said his family has been largely political.

Tugambire ku Jennifer

Yet, despite the historical political roots in his family, Bobi Wine's political muscle came to the forefront when he boldly came out to musically speak out against the excesses of the Kampala Capital City Authority (KCCA), especially the massive evictions of vendors, traders and other city dwellers, who authorities under the leadership of KCCA executive director Jennifer Musisi, said were operating illegally.

Titled, Tugambire ku Jennifer, Bobi Wine poignantly fought what he described as inhumane evictions, a move that endeared him to many city residents, especially the downtrodden, who praised his courage at a time when many politicians and leaders were shying away from speaking out on the matter.

Although, it was not easy to clearly predict Bobi Wine's next move, the political questions that he raised in the song paved the political way for the youthful musician.

When a group of top musicians in the country sided with President Yoweri Museveni during the 2016 general election by composing the all-star Tubonga Nawe song, Bobi Wine took a lonely path into the Opposition territory, openly siding with Besigye.

"We cannot keep quiet when injustice is going on in our country," he said, shortly after paying a courtesy call to Besigye's home in Kasangati.

At the time, Besigye was under preventive arrest at his home. following the 2016 general election. After visiting Besigye, Bobi Wine released a song, Situka, where he challenged Ugandans to fight corruption and injustice.

Family life

At one time, his wife, Barbie said there were times when they were poor and Bobi Wine used to walk from Kampala to Kamwokya so as to have more money to pay for recording studio.

Bobi and Barbie, as they are popularly known, met at the National Theatre in 2001.

Barbie was in her S6 vacation and Bobi was in his last year at Makerere University. They were both actors in the play Lady Will You Marry Me?

Bobi gave Barbie grapes and asked her if they could be friends but she was uncomfortable with him at first because she saw him as a 'bad boy' with dreadlocks. With time, they became close and developed a relationship.

On May, 12, 2007, Barbie introduced Bobi to her parents, Gershom and Joy Kagaaso in Ntugamo district. They have four children, but Bobi has a child with another woman who lives abroad. The couple lives in their mansion at Magere, in Wakiso district which sits on 17 acres.

The ghetto president has won over five music awards and released over 10 album songs. It is not clear that he will be able to balance music and political representation, but what is clear is that story of a Kamwokya ghetto boy, who has taken the political scene by storm, is just starting to blossom.

Time in Parliament

Bobi Wine emerged victorious in the Kyadondo East Parliament seat byelection in 2017 and served till 2020 when he upgraded his ambition to presidency.

During his time in Parliament, he formed the People Power movement and later became a presidential candidate for the 2021 elections under the NUP party fag. This was after the National Unity Reconciliation and Development Party (NURP) was renamed NUP. 

Presidential ambitions fail at first attempt

However, his first attempt at wrestling the reins of power from President Museveni proved futile as Museveni won the January 14, presidential elections with 6,042,898 votes (58.38%) against Kyagulanyi’s 3,631,437 votes (35.08%).  

Kyagulanyi, however, contested the results and, through his lawyers, filed an election petition on February 1, seeking the Supreme Court to overturn President Museveni’ victory over alleged election fraud and non-compliance with the electoral laws. 

Bobi Wine later withdrew the petition from the court, citing bias on the part of the judges. The withdrawal came a day after President Museveni, the Electoral Commission, and Attorney General filed their 185 affidavits.

Bobi Wine's timeline

2025

Declares intention to stand against President Yoweri Museveni in the 2026 general election

2024

Earned a law degree from the International University of East Africa while maintaining a music career

2021

• Lost presidential election to Museveni (35.08% vs. Museveni's 58.38%)
  
  
• Filed a Supreme Court petition challenging the election results on February 1
  
  
• Withdrew petition citing judicial bias after Museveni's camp filed 185 affidavits
  
  

2020

• Upgraded political ambition to the presidency, leaving Parliament after serving the Kyadondo East constituency
  
  
• Officially launched presidential campaign under the National Unity Platform (NUP)
  
  

2017-2020

• Served as Member of Parliament for Kyadondo East after winning the 2017 byelection
  
  
• Formed the People Power movement, galvanising youth support nationwide
  
  

2017

• Won the Kyadondo East parliamentary byelection in a surprising victory
  
  

2016

• Released "Situka" song challenging corruption after visiting Besigye under house arrest
  
  
• Defied musician peers by rejecting Museveni's "Tubonga Nawe" campaign song
  
  

Post-2011 

• Began speaking truth to power through politically charged songs, including "Dembe" and "Akalulu"
  
  
• Released "Tugambire ku Jennifer" criticising KCCA evictions under Executive Director Jennifer Musisi
  
  

2011

• Married longtime partner Barbra Itungo (Barbie), declaring: "From now on, I will be a man of immense responsibility"
  
  

2007

• Officially introduced to Barbie's parents in Ntungamo district
  
  

2001

• Met Barbra Itungo at the National Theatre during the play: Lady Will You Marry Me?
  
  
• Was in final year at Makerere University while Barbie was in S6 vacation
  
  

1998

• Completed Senior Six after attending nine different secondary schools due to financial constraints
  
  

Late 1990s

• Enrolled for Diploma in Music, Dance and Drama at Makerere University
  
  
• Began musical career while working as backup singer and fetching water in Kamwokya to afford school fees
  
  

Early Career

• Formed Fire Base Crew in Kamwokya, establishing himself as "Ghetto President" of Uganja land
  
  
• Released breakthrough song "Akagoma" that launched his music stardom