Because a Python sysadmin has been through all the transitions of packaging systems, all the nasty corners of "backwards compatible" changes, and knows how underlying changes to the operating system will affect your code, what the storage behaves like under load, and why one tech is not "better" than another. If you really hired an admin (cough, "reliability engineer") for a Python codebase that doesn't know Python, well, that's a different question altogether.
> I have regression tests to catch if an upgrade breaks anyyhing
You don't know what you don't know.
When you can reason about the multiple ways the above statement can fail, congratulations! You are now a seasoned sysadmin, the scorn of junior developers who just want to get things done (who incidentally read a great blog post the other day about a new packaging system that we should immediately transition to and by the way it's all backwards compatible).