In examining Donald Trump's presidential leadership, this article focuses on determining his efficacy as a political leader evident through three critical turning points in his presidency. His presidency began with a key legislative defeat, followed by a rare policy victory and in 2019, he controversially shutdown the government in a failed attempt to gain congressional funding for the US-Mexico border wall. By comparing the GOP attempt to reform healthcare with the passage of the Tax Cuts and Jobs Act, this article demonstrates how Republican legislative success relied upon a unified approach between Congress and the White House, with clear, long-established policy goals. Analysis of the longest government shutdown in US history provides insight into Trump's leadership style, presidential power and relationship with Congress. In all three cases, Trump's rhetoric failed to effectively support Republican policy efforts or convince Americans that their course of action was best. Indeed, Trump's rhetoric and actions often proved more contradictory and damaging to Republican efforts and to the overall future of the party. This article concludes that Trump inexperience and character was illequipped to be an effective political leader, evident in his few legislative achievements and the toxic environment of hyperpartisanship he left behind.