This Thesis will examine how the framing of ‘trolley problems’ incorrectly motivates arithmetic rankings of states of affairs by removing context. This is problematic because the context of these problems provides the tools to solve moral dilemmas by allowing one to analyze the relevant motivations, moral implications, duties, values, and personal and societal obligations that one has. I will discuss Samuel Scheffler’s charge that a paradox exists within agent-centered restrictions and how his abstract paradigmatic case leads to arithmetic rankings of choices, which are both unrealistic and lead to tragic and morally unacceptable decision making. I will argue that Allen Wood’s Middle Theory can help dispel the apparent paradox and demonstrate a better way to examine ‘trolley problems’. I will further discuss how Martha Nussbaum’s analysis of tragic questions illuminates the issues surrounding such problems providing a morally acceptable way to account for the occasional unavoidable harm that results in decision-making caused by solving ‘trolley problems.’ Taken together, Wood’s and Nussbaum’s theories and analysis provide potential solutions to ‘trolley problems.’