Though it is now widely accepted that candidate quality and strategic donors mediate Congressional election results, this insight has had little treatment in the literature on gubernatorial approval and elections. Rather than examine challengers and donors, most studies have attributed gubernatorial election outcomes entirely to voter behavior, which has led to misinterpretations of electoral data. This dissertation rethinks gubernatorial approval and elections, paying special attention to how potential challengers and donors in 2006 responded strategically to early signs of gubernatorial vulnerability. The analysis follows three steps. First, I explore the variations in gubernatorial approval existing in late 2005, with an emphasis on understanding why some voters hold their governor responsible for the state's economic problems while other voters do not. Second, I show that challengers and their financial backers responded strategically to these late 2005 approval ratings; governors who appeared vulnerable early on attracted politically experienced, well-financed challengers. And third, I examine the effects of challenger quality on the eventual result, showing that challenger quality matters less on election day than we might think