This article argues that the rigidity of the rule on ‘financial assistance’ in India must be relaxed to foster leveraged buy-outs. Section 2 traces the development of the provisions of the Indian Companies Act, 2013 concerning ‘financial assistance’, locating its roots in the House of Lords’ decision in Trevor v. Whitworth, and subsequently the UK’s Greene Committee Report. Section 3 analyses the dilution of the capital maintenance rule, a pillar of Trevor v. Whitworth by the UK in her Companies Act, 1981 and 1985, and by South Africa in her Companies Act, 2008. Based on the findings in section 3, that stakeholder interests can be preserved without prohibiting ‘financial assistance’, this section hopes for its transplantation into the Indian legal framework.