The effect of sound change and analogy upon inflectional paradigms has been traditionally described through Sturtevant’s Paradox, which states that sound change is regular but generates irregularity, whereas analogy is irregular but generates regularity. While past work has explored trends in sound change and analogy qualitatively, quantitative investigation with large data sets remains underexploited. We tackle this by exploring the effects of sound change and analogy from Latin to French in large etymologically paired inflected lexicons containing the complete paradigms of 310 verbs with 11,593 total forms. We employ a novel method combining the automated application of historical sound changes and entropy-based quantitative analysis to examine separately the effects of sound change and analogy. The results confirm the role of some oft-cited predictors of analogy like token frequency and morphological regularity, but offer no support for others like markedness. Results also confirm the complexifying role of sound change, and the simplifying role of analogy, on aspects of morphological complexity like the number of inflection classes and the amount of allomorphy, but suggest that these forces have no comparable effect on more modern measures of complexity like average conditional entropies between inflected forms.