This essay engages with Amin Samman's incisive 2019 text, History in Financial Times, which unfolds a philosophy of history for contemporary “financial times.” I turn first to Samman's concept of the strange loops of financial history, and so to the historical turn initiated by the subprime crisis of 2008. Then, I add the concept of strange portraiture to Samman's idea of strange history. Borrowing a metaphor from Oscar Wilde's The Picture of Dorian Gray, I trace the oscillating appearance of the linked faces of homo historia and homo economicus, which each offer distinct explanatory frameworks “under the sign of finance.” In this way, I suggest that we can also observe how capitalism transformed the meaning and possible trajectories of something like fate from invented origins to imagined destinies. In that frame, I explore how the loops that Samman underscores are also bound to the ways in which history and economics have competed and continue to compete for ascendency as modern sense-making epistemes with different time-binding effects.