A fence is not a natural place to sit, whether chain link or picket. The metaphor of “fence-sitting” has long connoted something improper, or at least unfitting.
At times, the phrase has implied opportunism — sitting on the fence until you see which side will win, like Aaron Burr’s depiction in Hamilton. In the 21st century, fence-sitting invokes Prince Hamlet more than Burr. It’s about unending indecision and oscillation.
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