Some crew members believe they see Moby Dick spouting, but it is only one unrepeated spout, and the mates warn that Moby Dick will spout regularly, if it is truly the White Whale. Finally, the call is raised aboard the decks—many crew-members at once—that Moby Dick is straight ahead, and Starbuck is once again left in command of the Pequod, as Ahab, Stubb, and Flask lower into their boats. The three boats chase Moby Dick, with Ahab attempting to meet the fish “head-to-head,” and each boat gets a harpoon into the whale’s skin. But Moby Dick begins spinning round and round, tangling the boats in their own harpoon-lines.
Ahab and his men pierce Moby Dick's skin with their harpoons, but Moby Dick uses those lines against the men (recalling Ishmael's descriptions earlier in the novel of the strength and dangers posed by lines
Ahab cuts his boat free with his much-loved harpoon, fashioned by Perth, but the other two boats are not so lucky, and are smashed against Moby Dick’s side—their crews get drenched and must swim to safety, clinging to bits of the broken vessels. Ahab, however, stays in his boat, only to find that Moby Dick is coming up from below, and he “smashes his forehead against the bottom” of Ahab’s boat, causing that crew to spill once more into the ocean, and Ahab to cling to one half of the broken vessel and to lose his harpoon.
Ahab must abandon his harpoon, the one he believed to be powerful enough to kill Moby Dick. This, again, is a bad omen, making it seem that Moby Dick will not be killed after all, but that the whale instead will be the master of Ahab and the rest of the crew. Ahab has now survived two different falls out of his boat, despite his false leg.
The Pequod manages to scoop up all the sailors, mates, and Ahab, who are swimming in the nearby waters, as Moby Dick glides quickly away. But Ahab realizes that Fedallah is missing—that he was trapped under Moby Dick when the whaleboats were jammed against the whale’s body by their harpoon-lines.
Ahab is horrified by the news that Fedallah has been lost. Ahab sees Fedallah is central to his efforts to kill the whale.
Ahab mourns his friend and comrade in battle, and wonders if this doesn’t spell doom for his mission. Starbuck, once Ahab is back on board, pleads with his captain to abandon the chase, saying that his boat has now been destroyed twice, and that Moby Dick will kill him and perhaps the rest of the crew. Ahab also shows that his new-made ivory leg has been broken, “once again,” by the whale—this is more evidence, to Starbuck, that Ahab’s mission is an impossible one. But Ahab says that he and Starbuck were always meant to have this philosophical battle, that “’twas rehearsed by thee and me a billion years before this ocean rolled.” Ahab also announces that, like any drowning person, Moby Dick will surface one more time, only to be slain after his third and final surfacing. The crew sleeps for the night, and Ahab dozes with his face eastward, awaiting morning and the final day of the chase.
With Fedallah dead, Ahab's harpoon lost, his boat twice broken, his leg cracked one more by Moby Dick, it seems obvious to all reasonable people that to go out and face Moby Dick for a third time would be to invite death for himself and perhaps everyone. And Ahab himself wonders now if he will lose this battle. But Ahab also is not a reasonable person. Unlike Starbuck, he is on a quest to which he has given himself completely. Theirs is a philosophical disagreement that has no solution, between those counseling reason and those who don't see reason as a primary concern. Ahab seems genuinely to believe that his struggle with the White Whale is a version of man’s same struggle that has been playing out since the dawn of time; man’s fight with nature, with God, with his own terrible fate, which attempts at every moment to destroy man. Although the crew, at this juncture in the novel, is exhausted by a two-day-long whale-hunt, Ahab seems only to have grown more vigorous during this long struggle; he cannot sleep, but can only wait as the whale comes back for a third and final day. Meanwhile, the number three has long been significant in biblical and other stories, with the most notable antecedent being Biblical—Jesus died and took three days before he rose again.