The aim of this paper is to discuss the impact that the “second wave” of technological unemployment may have on economic theorizing. According to a number of recent contributions (e.g. Brynjolfsson and McAfee 2011, Freeman 2015, Ford 2016) the new wave of technological unemployment, i.e. that affecting economy in the beginning of 21^st century, is radically different from the old one. While the old one mainly lowered wages for unskilled workers without a relevant impact on unemployment, the new, based on artificial intelligence, is hitting both skilled and unskilled workers, lowering wages and virtually reducing to zero human employment in (almost) all industries. The resulting mass unemployment will require special redistributive policies, typically in the form of taxing robots and subsidizing unemployed humans. It is worth noticing that in the great majority of countries this phenomenon has not yet started, so that empirical studies have scarce relevance for assessing the theme (an exception being Acemoglu and Restrepo 2017 contribution). Nonetheless, few doubts exist on the future empirical relevance of the phenomenon, so that economists should begin asking themselves whether mainstream theoretical tools can successfully handle such radical changes. In particular, it appears rather difficult for the standard approach (i.e. for Economics) to deal with a reality in which social classes and class struggle (few robots’ owners vs. many unemployed humans) regain a role, labor productivity is insignificant and uncorrelated with the (subsistence) wage/subside received, price signals loose importance, redistributive policies gain relevance with respect to the optimal allocation of scarce means, and so on. These characteristics may bring back economic theorization to the years of classical Political Economy. Indeed, the main focus of Political Economy was on social classes and redistribution of surplus. Similar themes will be on the stage in the near future, when the problem will be extracting surplus from robots and redistributing it to unemployed so as to guarantee subsistence for humans and demand for commodities produced by robots. The paper first sketches the history of technological unemployment and compensation theory from the luddites till today. Then, it describes the main characteristics of technological unemployment 2.0 and its possible solutions, focusing mainly on the key policy of taxing robots to subsidize unemployed humans. Finally it discusses the comparative capability of Economics and Political Economy to theoretically systematize this new framework, showing that when distributive questions are on the stage the latter appears more effective than the former.