Abstract This article explores a pair of powerful but competing symbols in the Chilean human transitional justice process: ‘pobres viejitos’ (poor little old men) and country club prisons. The symbol of the ‘pobres viejitos’ is used very effectively by conservative elements of Chilean society to argue the futility or even inhumanity of punishing perpetrators of human right violations so long after the commission of their crimes. In turn, to victims and more liberal segments of society, the country club or ‘five star’ prison for human rights violators stands as a symbol of impunity and the failure of the Chilean state to do justice for the crimes of the dictatorship. This article examines the power of these symbols in undermining support for transitional justice efforts, as well as the externalities of the debate. The fate of the ‘pobres viejitos’ and whether to release the from even their relatively comfortable places of confinement has bled into debates on penal reform for other elderly prisoners. This mostly negative externality suggests the need for international and regional courts (or countries not in the throes of transitional justice processes, particularly delayed ones) to lead the way on the articulation of human rights norms related to the trial and punishment of elderly prisoners.