While the grand narratives of political leaders and leadership in parliamentary democracies tend to centre on victorious campaigners, prime ministers ‘inheriting’ the office from their predecessor between two parliamentary elections are a widespread occurrence in constitutional practice. Focusing on four Westminster democracies (Britain, Canada, Australia and New Zealand), this article inquires how such heirs apparent have fared in terms of prime ministerial performance. Although in light of their experience, expertise and public recognition, heir apparent prime ministers can be, and have been, considered to be particularly well placed to succeed, when eventually securing the most powerful political office, most of them have actually been conspicuous under-performers. The single most important and strongly counter-intuitive finding of an empirical investigation of different prime ministers is that extensive experience in government, both in terms of duration and diversity of ministerial offices held, seems to correlate more with failed rather than particularly successful premierships.