It's from the early days of Greatest Gen, and references Captain DeSoto of the USS Hood (NCC-1703). DeSoto and the Hood made several appearances in TNG, and Ben and Adam leaned into his chill vibes, theorizing that the Hood would be a great place to work.
It's also an allusion to the phrase Friend of Dorothy, an older euphemism for LGBT people.
I think it was originally jokingly conceived as a sort of passphrase or shibboleth for fans of the pod to identify each other without revealing their embarrassing enthusiasm to outsiders, e.g.
Q: "Are you a friend of DeSoto?"
A: "Best boss I ever had!"
Excellent documentary about the legacy of violence in Indonesia https://www.imdb.com/title/tt2375605/?ref_=ext_shr