I think you misunderstand my motivations for putting the two of them in the same room. If there's one thing that I've learned over my years in this world, it's that the magic happens between people, not within any one person's mind. There are three "people" in my scenario - Guido, Jerry, and the audience. Somewhere in that conversation, an idea might be sparked.
If you put Isaac Newton in the same room as George Washington, it'd be two brilliant people, but I'm not sure they'd have much to talk about. They think about different problems.
What might be interesting, come to think of it, would be a Chat Roulette, but populated with these sorts of folks.
In practice I find this rarely to be the case unless you as the facilitator are also commensurately cognitively capable (say that three times fast), otherwise you're sort of placing an excessively undue amount of pressure on them.
If you wanted to talk about robust programming, quantum gravity, differential geometry, education, or a slew of other topics....
As a footnote, I love Python, but someone like Jerry outclasses Guido intellectually. Guido really only did one thing, which is Python. Jerry has done dozens of things.