There is no adequate survey of ancient writing on chance, much less of its possible influences on writers in the last few centuries, and I am not the scholar to make good the deficiency. But it occurred to me that in the playful, albeit serious, spirit of Renyi's Letters, I could try to show some parallels between ideas central to my own recent work with probability models and discussions I've happened across in my recreational reading of the classics. I will refer particularly to Plutarch, who lived about A.D. 40-120 and whose surviving work is voluminous by comparison with that of almost any other ancient writer with equally broad interests. First, I note a number of general and recurring themes in Plutarch's Moralia and Lives (the two large collections of essays and biographies comprising his oeuvre) that seem to anticipate some of the topics dealt with by writers on probability in the scientific age; and then I mention in detail some specific passages in Plutarch that could be used in a didactic presentation of the probabilistic Rasch measurement model, on which my own research has been focused for the last several years. Allow me to follow Plutarch's own practice of quoting extensively from the sources.