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trailer couplings need to exert some downward force on the towball, if there is no downward force or worse still an upward force you will experience severe trailer sway. if the second trailer exerts downward force on it's towball it might negate the downward force of the first trailers coupling, causing swaying. in both truck pictures you posted all trailers were supported front and rear by wheel sets, simple box trailers only have supporting wheel sets (1 or 2) near the middle, allowing them to pivot, when they pivot the coupling up, things can go pear shaped very quickly.
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