Johannesburg Family Fears for Winston Cliff, 65, Held in Djibouti Prison Without Answers

Johannesburg Family Fears for Winston Cliff, 65, Held in Djibouti Prison Without Answers

  • Winston Cliff, a 65-year-old Johannesburg businessman, was arrested in Djibouti in August 2026 under unclear circumstances
  • His family has received conflicting explanations for his detention and has been approached by individuals demanding money
  • South Africa's DIRCO acknowledged the family's frustration but said it cannot intervene in Djibouti's legal processes
A post.
A woman is emotional while sitting in a church pew. Images: SOPA Images / Contributor/Getty
Source: Getty Images

The family of a Johannesburg businessman is living in fear after he was detained in a Djibouti prison following a trip to the East African nation to explore infrastructure opportunities.

According to TimesLive, Winston Cliff, 65, first travelled to Djibouti in March 2026 to pursue prospects in mining and construction. He was arrested on or around 24 August 2026, together with his local business partner, Madina Auuled Robleh. Robleh was released on the same day. Cliff remains held at Gabode prison.

Contradictory reasons for detention

What has alarmed his family most is the string of conflicting explanations they have received for why he is being held. One account attributed his arrest to an unpaid hotel bill. The most recent allegation is far more serious: that Cliff forged the signature of a government minister.

Read also

North West police identify suspects in Donovan Marx farm attack

PAY ATTENTION: You can now search for all your favourite news and topics on Briefly News.

His daughter Kim and son-in-law Xolani Khuzwayo have since been contacted by unknown individuals requesting money. A lawyer based in Djibouti, whose legitimacy the family doubts, told them that two men had orchestrated Cliff's arrest to access his finances. That lawyer then demanded a legal fee of $2,500, roughly R42,000.

Family turns to DIRCO for help

The family has lodged a formal complaint with South Africa's Department of International Relations and Cooperation. DIRCO spokesperson Clayson Monyela acknowledged how distressing the situation has been for the family but was clear that the South African government has no authority to interfere in Djibouti's judicial proceedings.

The suspected lawyer has since arranged a video call between Cliff and his family, offering them brief visual confirmation that he is alive. However, his legal position remains deeply uncertain, and the family has no clear path forward.

A post.
A man in handcuffs. Images: picture alliance / Contributor/Getty
Source: Getty Images

More on crime and justice in South Africa

Read also

Pinetown viral hijacking case: Man faces 10 charges as court keeps him behind bars

Source: Briefly News

Authors:
Nerissa Naidoo avatar

Nerissa Naidoo (Human Interest Editor) Nerissa Naidoo is a journalist and editor with seven years of publishing experience, specialising in human-interest features, societal developments, and breaking crime updates for Briefly News. Having worked as a copy editor and content accuracy specialist for international publications like National Today and Entail.ai, Nerissa applies rigorous fact-checking and ethical standards to sensitive news stories, including police updates, community affairs, and public safety reporting.  Contact: nerissa.naidoo@briefly.co.za