Bitter End
Which end is the bitter end?
It turns out that the “bitter end” of a rope is the end you secure or bend to the bitts of a ship, while the other end secures the anchor. If you are hoping to anchor in very deep water, you pay out more and more line and hope that the anchor will hit the sea floor. Instead, your line runs out all the way to the bitter end, and then you are up a creek without a paddle. Thanks, W.H. Smyth, The Sailor’s Word Book, 1867.