Michael Bailey

Michael began his career as a Candidate Attorney at Cliffe Dekker Hofmeyr in 2021. He was appointed as an Associate in 2022. Prior to joining Cliffe Dekker Hofmeyr, he worked in-house at a commodity brokerage. 

Michael was promoted to Senior Associate in April 2025.

• Advising major lending institutions and borrowers on equity funding (including preference share funding), project finance and debt finance.
• Drafting and reviewing various finance documents including facility agreements and the appropriate security documents.
• Conducting due diligence investigations and drafting due diligence reports.
• Public Investment Corporation SOC Limited in relation to the subscription of shares in the Africa Finance Corporation amounting to ZAR 1,7 billion.
• Old Mutual Limited on an amendment and restatement facilities agreement to purchase additional residential properties for a deal value of R500 million.
• Grindrod Bank Limited in relation to: two facility agreements to finance a rooftop solar system at a commercial building; and funding to FEC Prop Proprietary Limited to purchase listed shares for a deal value of R129 million.
• Grand Casino Investments Proprietary Limited on the subscription of preference shares in the amount of R100 million.
• Development Bank of Southern Africa on its facility funding to a state-owned enterprise for a deal value of R500 million.
• Taquanta Asset Managers Proprietary Limited on its financing for the purchase of a 49% undivided share in a shopping mall valued at R242 million.
• Futuregrowth Asset Management Proprietary Limited on its term loan facility to a listed property developer valued at R272 million.
• Food Lovers Holdings on its extension of its revolving credit facility for a deal value of R600 million.
• Aleyo Growth Fund 1 Partnership on its subscription of debentures for a deal value of BWP100 million.
• Vukile Property Fund Limited on its vendor loan finance for a deal value of R24 million.

• The Legal 500 EMEA 2024 - 2025 recommended Michael in banking and finance.
• IFLR1000 2025 recognised Michael as a 'rising star' in Banking and Finance.