A failed orginization or group of idiots. Doomed to failure and full of ineptitude, they still contiune to sail away on the sea of stupidity.
In extreme circumstances, one man can be catergorized as a failboat in and of his/her self.
Pictures of capsized or rolled boats usually shown as an example of what happens when the crew does something.
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.