@lordbowlich Chesterton is a British writer of the early 20th C. I think the poor here refers to the proletariat. In Great Britain, land had been enclosed as capital and agricultural work formalized on contractual terms by this point, so to some degree proletarianized, I think.

You might make a similar critique with respect to the frontier farmer in the US, Jefferson's yeoman independent smallhold. They could be quite poor! I just don't think these are the classes Chesterton is referring to.