The phrase "leather boat" is an idiomatic expression that means to fail or come up short in a task, challenge, or opportunity. The origin of this phrase comes from the game of baseball where if a batter strikes out (i.e., fails to hit the ball) three times in one game, they are said to have "gone down swinging" - which is another way of saying that they tried their best but still failed. In some regions, particularly in North America, this phrase has been extended metaphorically to refer to any situation where someone tries hard and fails, or misses out on an opportunity despite their efforts.