In the United States, "good ol' boy" actually has a complicated cultural meaning. Here's Wikipedia's article about it:
https://en.wikipedia.org/wiki/Good_ol'_boy
From the article I find, rather to my surprise, that the American Heritage dictionary actually has a definition:
"A man having qualities held to be characteristic of certain Southern white males, such as a relaxed or informal manner, strong loyalty to family and friends, and often an anti-intellectual bias and intolerant point of view."
To me--again, in the United States--it suggests someone who lives in one of the southern states or in the "sunbelt," is white, has a position in the local power structure and a degree of local influence, may not be extremely wealthy but is probably well off, is probably not especially well educated (with the possible exception of lawyers), possibly belongs to a golf club, service club, or lodge, and is generally respected by other good 'ol boys. He is probably not a "southern aristocrat." He might own a car dealership. He might be a real estate developer. He is almost certainly a Protestant.
Good ol' boys are "cronies" and look out for each others' interests.
It has both positive and negative aspects. It isn't necessarily negative, it depends on the context.
I need to warn you, though--my personal knowledge of good ol' boys comes mostly from novels: John D. MacDonald's wonderful Travis McGee novels, from Carl Hiassen's comic novels, Elmore Leonard... and come to think of it, most of them are set in Florida.
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