After becoming a sailor to escape mounting debts and disfavor within his family, David Cheap is desperate to prove himself, craving the opportunities for heroism and glory that he believes only a captainship can provide. However, he is also egotistical and inflexible, and lacks many of the qualities that make a good leader, particularly under dire circumstances. The Wager, having been repurposed from a merchant vessel, is an especially difficult ship to navigate through the perilous waters it encounters on its voyage. From the beginning, Cheap faces difficult circumstances that bring out the worst in him. In this way, Cheap’s downfall over the course of The Wager is self-perpetuating: the more pressure there is on him as conditions deteriorate, the more uncooperative he becomes, lashing out at his officers rather than accepting their help, which contributes to their distrust in his leadership. Over time, this pattern creates a rift between Cheap and his crew that steadily widens until the crew feels its best course of action is mutiny.

During the castaways’ time on Wager Island, Cheap prioritizes concerns about his own authority over the wellbeing of his crew, which ironically leads the crew to mutiny. Not only do Cheap’s paranoia and insecurity degrade his own leadership, but his retreat into seclusion opens the door for others to emerge as stronger leaders in his stead. While Cheap fixates on the dream of completing his original mission to meet up with Anson in Chile, John Bulkeley builds sturdy cabins for the men and John Cummins engineers a new ship from the wreckage. By the time Cheap shoots and kills Henry Cozens over unfounded suspicions of organizing a mutiny, the other men are well-prepared to do just that, thanks to the void that Cheap’s absence has already created. In the end, like in the multiple instances of imperial hubris that Grann references throughout The Wager, Cheap’s own arrogance is his worst enemy.