After living and working abroad, Brennan returned to South Africa to commence articles at a Sandton based boutique law firm specialising in mining and maritime law. Brennan ceded articles to a Port Elizabeth based full service law firm where he completed his articles. Upon completion, Brennan was retained as an associate and appointed to specialise in and manage the firm’s banking litigation department where he became responsible for serving various major credit providers nationally. Throughout this appointment, Brennan gained specialised experience in large scale securitization and foreclosure type matters, secured asset recoveries, general debt recoveries and debt review related matters.