I think that there might be some marginal gain on truck/trailers if a large amount of air were allowed to enter the front of the trailer and flow through the internal trailer load and be blead into the rear dead air area. But as Hucho pointed out, it isn't simple. The internal resistance of the trailer now comes into consideration, and they are usually very full and well blocked.
Of course, this would only work with covered trailers, and then only when the weather was dry.
As others have said, there are probably more productive tractor/trailer approaches which have greater gain. Full skirting around all the wheels, well radiused corners, and boattails come to mind.
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