As Uganda’s presidential nominations come closer, Kyadondo East member of Parliament Robert Kyagulanyi Ssentamu has vowed to run for the top job. Best known as Bobi wine, Kyagulanyi describes President Museveni’s 36 years in power as a dictatorship. Bobi wine, a ugandan musician – turned politician was once known as the “ghetto president” but 2019 became the year he announced a bid to challenge Museveni for presidency. Museveni, who has been Uganda’s president since 1986 termed Mr. Bobi wine an enemy of Uganda’s progress because he asks foreigners not to invest in Uganda until there is a change in leadership. Museveni is also trying to connect with young people and slum dwellers who are believed to have support for Bobi wine. Mr. Museveni has also resorted to recruiting musicians which critics see as fighting Bobi wine’s rise. It was in 2017 that Mr. wine came into the ears of Ugandans who believe in politics after winning the hotly contested Kyadondo East parliamentary seat with over 77% of the votes casted. Bobi wine became more famous, when the Ruling NRM party introduced the controversial Amendment Bill of Article 102(b) which sought for the changing of presidential Age limit. Bobi wine together with other opposition politicians fought against the amendment but at last NRM took the biggest share due to the fact that it has the biggest number of parliamentarians. The introduction of the social media tax (OTT) also made Mr. Bobi wine famous and eventually he launched his People Power Movement. During recent by elections that saw Bobi wine involved, were all won by candidates he campaigned for until the controversial election of Arua Municipality when he was arrested by security operatives saying that he(wine) and his group had disturbed and disorganised the arrangement of Mr. Museveni’s convoy hence hitting of his cars. Bobi wine was highly tortured and detained and this was seen catching the minds of the International community hence demanding for his immediate release. Analysts say Bobi wine’s quick rise in politics is because of young people tired of false promises. As bobi wine is ready to contest against Uganda’s longest serving leader Mr. Museveni, analysts say that he sured be more ready and prepared because Museveni being an incumbent is very strategic when it comes to politics but again Mr Museveni should also watch-out for Bobi wine. 2021 will decide it All.