[Curulin]

Interesting thought!
I think that maggot was just one of Tom's informers, and perhaps he also had ways of gathering information from Men and Elves. He certainly knows Gandalf, who goes to have a long talk with him at the end of RoTK, and he probably got information from him about the goings on in the wider world.
Perhaps he esteemed Maggot so highly because of Maggot's willingness to speak with Tom, something which would be quite rare. Maggot probably became more wise the more he met with Bombadil.
I do know, if you are interested, that there is more on the relationship between these two in a poem entitled "Bombadil Goes Boating" by Tolkien (In which Tom calls Maggot an "old friend" and they go drinking together), so if you wanted to try and find more clues you could go and read between the lines there! The poem also mentions Maggot's sons, so perhaps the connection was hereditory!
I'd be interested in what conclusions you came up with!
Curulin