CMU Common Lisp has had an innovative, high-performance compiler called Python since before van Rossum invented the scripting language. A Common Lisp compiler and a programming language are, seems to me, very much in the same market space; I do not think the PSF could successfully argue in court that they do not overlap -- certainly not at the same time they were arguing that a cloud service does overlap a scripting language.
I'm sure van Rossum was unaware of CMUCL's Python when he named his language. But that doesn't matter in trademark law; you don't get to claim a trademark someone else is already using just because you didn't know about them.
And I believe that using a mark that was already in use gives you a very weak claim, if any, to your trademark.
CMUCL is, by the way, still in use.