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29. John Henry

The 2011 blunders were countless for Red Sox owner John Henry. A momentous September skid was lowlighted by his confounding decision to reward his employees for their ineptitude, buying each of them a $300 pair of headphones and inviting them to party on his yacht. Then there were the nasty rumors regarding Terry Francona and prescription meds leaked from within his organization, with limited damage control to refute them. And that's merely scratching the spineless surface. Not a coincidence that he resembles Darth Sidious.
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