E-Sir: A Simulation of Destiny, Things Death Stole from Us

By Silas Nyanchwani

Published on 17/03/2023

There are two types of Kenyan musical fans: those who believe that E-Sir is the greatest Kenyan rapper ever and those with bad musical taste.

Those with bad musical taste insist that E-Sir is overrated and is only glorified because he died young. This is a totally unfair assessment of his short-lived career. Yet, within the two or so years he happened in our music scene, he left us with an album of 13 songs. That is prodigious.

Those who lived in the era of music albums know the pain that came with buying an album of your favourite artist, only for the album to have one or two songs, and the other 12 tracks being totally unlistenable. Yet, all of E-Sir’s tracks, from Boomba Train to Moss moss to Kamata, to Hamunitishi, to Saree, to Lyrical Tongue Twister are totally enjoyable, each with a unique beat, versatile flow, and unique message.

E-Sir’s greatest gift was his voice, that distinct, most Kenyan tenor, and the gift of the language. His Swahili and sheng were impeccable. Whereas the Ogopa stable was more Bad Boy than Death Row, one can detect E-Sir wanted to have the flow of Notorious B.I.G, but his flow was more poetic like Tupac’s. But really, he sounded like E-Sir, in a way that nobody could duplicate.

It is wrong to judge him by his album when he was barely 21. All his songs, like any songs of a rookie, revolved around partying, his growing up in South C, odes to friends, and the Ogopa DJ stable. He was barely starting, and when starting, you have to dispense with such from the word jump. E-Sir was like a student who joins Form 1, becomes the best in his class in the first term, and then dies. Everyone can guess that had he lived, he would have gone to pass his KCSE, or in this case, he would have still remained one of the best rappers in East Africa.

What you detect in that first and only album is a kid immensely talented in composing, writing, and delivering good music. His vocal authority was precocious. His rhymes and wordplay were not yet sharp, but you could sense and predict how he was likely to grow to be a monster rapper out of the Ogopa DJs. He was still experimenting, and he had struck gold. All he needed to do was make more music and he would have been the ultimate G.O.A.T.

From where I sit, he was likely to be the undisputed rapper of the 2000s. Jua Cali went on to rule the 2000s with his own blend of Eastlands rap, and did put up a good shift but E-Sir would have been the King.

So, how would have E-Sir’s career panned out?

The best way to predict his career is to look at the careers of his contemporaries. Most rappers of his generation have faded from our collective conscience, but his biggest side-kick, Nameless, is still around, churning a song or two every two to three years. Could E-Sir have possessed similar longevity? Would he have faded off, becoming a washed-up, disrespected rapper? The answer lies in the fact that E-Sir was talented. And talent with discipline, with a bit of hard work, can take a young man places. Importantly, E-Sir’s Muslim background would have played a role in his success or failure.


In 2002/3, Kenya was still in a celebratory mood, having kicked President Moi out of power after 24 years of misrule. Moi suppressed all manner of expressions, and Kenyans were deeply depressed and repressed. Our country was prudish because we had a praying president who out of the church did the opposite. Thus kicking him out called for long celebrations. All the music from Ogopa DJ, R Kay, Calif, and other record labels was interested in riding on that celebratory wave.

E-Sir’s Album, Nimefika

E-Sir died in March 2003, when President Kibaki had been in power for barely three months. So, I predict that in 2003, E-Sir was most likely to release more club bangers, and do more collaborations with artists at Ogopa and he was likely to be their biggest ambassador.

Two things were likely to improve E-Sir’s music. In 2003, Calif records happened in the scene with an aim to end Ogopa DJs’ dominance. Ogopa DJs with their South B address were middle-class and had birthed a new Kenyan sound called Kapuka. Calif on the other hand, with their California address in Eastlands was about to give us Genge, a similar sound to Kapuka, but lyrically the two stables couldn’t be more different. Clemo of Calif, favoured a laid-back, narrative rap, as Nonini explained in one of the episodes of CTA. Their conversational rap laced with tales of the ghetto was an instant hit with Kenyans. Their lyrics laced with humour, profanity, and relatable tales from the hood gave Ogopa a run for their money. Ogopa was good at beats and videos, and Calif was better at writing good music, and run-of-the-mill videos, due to budgetary problems.

Lyrically in terms of storytelling, Ogopa only had E-Sir who could write songs in Swahili and sheng, but was he good enough to match the Calif stable? The answer is an empathic yes.

But the beauty of Ogopa and Calif was that, like Chinua Achebe once said, “where one thing stands, another one can”, thus we embraced both. At the time, the FM radio was volatile; each evening we tuned in to the countdown of the Top 7 songs at Kiss 100. Eve D’Souza with her Hits Not Homework would also go ahead to develop a healthy hip-hop culture in Nairobi.

My guess is that competition from Calif would have sharpened E-Sir, bringing the best out of him. I doubt if he would have loved to be drawn into beefs between fellow rappers or stables since his talent was outstanding and barely needed any side shows to survive. It is interesting how he would have handled the K-South crew who took a dig at Ogopa DJs.

His sophomore album would have either been similar to his first, an improved version and or average, given he had come in with so much energy. There is what I call ‘early burnout’ where you work hard in your early years that your first one or two albums become the only ones. Only the good one (s). Lauryn Hill, anyone? But this was unlikely to be the case, given the versatility of the songs in the first album.

His third album which was likely to come out sometime in 2006, would have been his most seminal. With his first album, he had set a trend of releasing albums and would have been inclined to keep up with the trend. This set him apart from other artists who opted for singles and collaborations in order to stay in the market.

I suspect around the third album, E-Sir would most likely have broken up with Ogopa and would have gone to other producers. His heart was in hip-hop, and he would have ended up with a stable that was more inclined towards hip-hop, as he followed what was in his heart. K-South? Who else? R Kay’s productions were more soulful, a bit too soft for hard hip-hop. Musyoka would have done a few songs for E-Sir in the freelancing period from around 2007-09. Or E-Sir, if he had business acumen, would have come up with his own production company.

The post-election violence would have shaped his career. There was a serious artist in him committed to activism, and the violence would have called on him to channel his inner Muslim, his inner artist, to run away from the music of partying, and drop a more conscious album. That would have been around 2010, just in time to hand over the baton to Juliani, who to me was his heir in terms of vocal delivery, though more conscious, lyrically.

In the world of music, most artists fade off within a decade. Indeed, that Ogopa DJ class of 2000 did fade off by 2010 and was reduced to a few hits each passing year.

But I suspect up to around 2015, E-Sir would have added another album and featured in collaborations with upcoming artists. Had he remained with Ogopa, or gone to set up his own stable, he would have mentored a whole generation of young rappers. And if he took the backseat to write songs for young people, he would have worked in the background, only insiders knowing what he is up to.

My hunch is that his Muslim faith would have shielded him from scandals, and he would have married the hottest Muslim celebrity or non-celebrity of his generation and settled into marriage. I can’t rule out a celebrity divorce along the way. But that will be over-speculation.

Thus my guess is that he would have remained relevant up until 2015, before going to influence music from behind the scene, but his legendary status would have been established. And he would be highly respected, though in Kenya, as Nyashnski said, we don’t respect our legends.

His career would be comparable to that of Nameless, Nyash and Nonini. His later songs may not have struck a good nerve like his earlier ones, but so what.

I suspect because of his clean boy image, he would have made money from endorsements like Jua Cali, and with good management, he would be wealthy enough. Wyre comes to mind.

But we will never know. All this is speculation, of a man who deeply loved his music. Time to bump to Nimefika Jo. Thanks to Nons for pointing out that the song was a sample of Black Rob’s Whoa. And listening to the album, I notice that E-Sir did borrow a tune from B.I.G and Jay Z. His preferences were very East Coast. And if he was born American, he would have fit into that New York rap craze.

Keep resting easy, Champ.

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