This paper focuses upon the Flamingo, a 1940's casino and hotel in Las Vegas, Nevada that was imagined by Hollywood restaurant owner Billy Wilkerson and realized by mobster Bugsy Siegel. Using newspaper articles, FBI files, advertisements, and other such primary sources, the paper traces Wilkerson's involvement with the Flamingo, as well as Siegel's eventual rise as the project's head. Three main secondary sources were examined in order to provide historical context for the Flamingo, Wilkerson, and Siegel. Firstly, Wallace Turner's 1965 work Gamblers' Money: The New Force in American Life</em> examines Las Vegas's economy and the rise of the casino hotels. Secondly, John L. Smith's 1997 essay "The Ghost of Ben Siegel" focuses upon Siegel's evolving image and his lasting hold on Las Vegas folklore. Lastly, Larry Gragg's 2015 biography, Benjamin "Bugsy" Siegel: The Gangster, the Flamingo, and the Making of Modern Las Vegas, explores Siegel as both a mobster and a businessman, concluding that he was much better suited for the former. Both Wilkerson and Siegel were intoxicated by Las Vegas's corrupting allure of wealth; the city simultaneously entranced and destroyed them. Yet, although they both ultimately failed in their roles as Las Vegas capitalists, I argue that the Flamingo paved the way for future casinos and hotels on the Strip, thus inaugurating modern-day Las Vegas.