This was a lot of fun -- start to finish. I understand and appreciate your idea of influence, heft, legacy, etc, which is a completely fine standard for a Mt. Rushmore.
However, the ancient candidates, versus the "Moderns," got a 2,000-year head start! I think about how many students read, discussed and wrote about Plato and Aristotle before Descartes was out of his diapers. How might the Moderns compare 2,000 years from now?
Looking at philosophy's edifice now, so much was Plato's and Aristotle's work, but if the edifice had to be recreated from scratch, might the components of the Moderns, although small, be harder to reproduce?