
Success stories often proclaim the popular ‘grass to grace’ mantra to depict how individuals transition from humble beginnings to riches and success. However, what most people forget is that the path can easily be reversed. This piece spotlights five Kenyan celebrities who embarked on success but, somewhere along their journeys, endured dramatic reversals.
Dennis Oliech
While a striker for Harambee Stars, Oliech set a record by scoring 34 international goals. Often referred to as ‘The Menace’ of Kenya’s football, Oliech was one of the first Kenyans to play in European leagues. A few years after retiring from his career in Europe and Qatar, Oliech began struggling financially.
Though he was adamant about admitting it, close allies revealed how Oliech’s extravagant lifestyle, including extended club partying, was rapidly draining his finances. To defend his position, Oliech attributed his thinning wealth to the heavy financial cost of catering to his mother’s cancer treatment.
Conjestina Achieng
During her prime, Conjestina was the undisputed queen of the ring across the region. Besides being Kenya’s first female boxer to gain global recognition, local fans always praised her ‘Iron Fist’ for knocking out opponents in the ring.
While at her pinnacle, Conjestina suddenly succumbed to alcoholism, which kept her in and out of rehabilitation centres. Later, official reports cited mental health issues as the root of her struggles.
Magix Enga
In the mid to the late 2010s, Magix Enga was among the crème de la crème of music production in Kenya. As a singer-producer, he dominated the industry with several hit songs until his trajectory began to decline in 2023. His sudden rise to fame and eventual fall caught Kenyans off guard, revealing the often-overlooked vulnerability of creative success.

Although Magix Enga lived in hardship for a while, he recently revived his music career and has released some new songs.
Colonel Mustafa
As a pioneer in his field, Mustafa is one of the most popular names in Kenya’s music industry. His hit song “Monalisa” endeared him to Kenyans long before the era of YouTube.
Despite his fame, Mustafa has become a pale shadow of his former self. Recently, even after receiving over 1 million in donations from his fans, Mustafa continues to struggle.
Omosh
As one of the most relatable characters in the Tahidi High drama series, Omosh earned a name in the industry, especially with his street slang and swagger that resonated with high school students and youths in general.
However, he began experiencing issues with alcoholism, which jeopardized both his marriage and career.







