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I agree with your assessment... the dating of such a hill figure is nigh impossible, as scouring and natural hillside erosion may have actually deepened the figure over time. From a purely stylistic standpoint, there is nothing about the figure which links the giant to either the 17th century or to Oliver Cromwell specifically. Everything about the 'feel' of the giant points to a more ancient, and primal origin. If it had been meant as a work of 17th century political satire, then there almost certainly would have been explicit visual clues directly linking the giant to Cromwell -- if for nothing else, then so that the average contemporary viewer at the time could understand the figure for what it was.
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