A person who leads an effort doomed by its own stupidity and innability.
Some failboat captains and an honorable mention.
Arthur Anderson was the biggest failboat captain of modern times.
Many of the Roman Emperors. (Think: instead of, I will not negotiate with terrorists, think: Non spectabo cum tribus, or I will not meet with tribes.)
Adolf Hittler. (He was high too, maybe that got him promoted from ensign.)
George Bush narrowly avoid the title because America somehow survived.