The $6 million gamble that defined the Las Vegas Strip

Entertainment · Published 8 October 2026 Swipe more like this →

In short: In 1945, Billy Wilkerson envisioned a luxury resort on the edge of the desert. But a partnership with mobster Bugsy Siegel turned a $1 million dream into a $6 million battleground of mismanagement and violence, leaving a legacy that still defines the Las Vegas Strip today.

The Flamingo's origins are a tug-of-war between two men: Billy Wilkerson, the founder of The Hollywood Reporter, and Benjamin "Bugsy" Siegel. Wilkerson purchased the land in 1945, but lacked the capital to realize his vision. This financial gap led him to partner with a trio of mobsters, including Siegel, to secure financing. While Wilkerson provided the initial concept, Siegel eventually took control of the project through the Nevada Projects Corporation, much to Wilkerson's dismay.

The construction was fraught with tension. Siegel successfully argued to bypass a post-WWII building freeze to continue work, but his management style caused costs to skyrocket from an initial $1 million estimate to a final $6 million. The tension was so palpable that construction managers reportedly struggled to receive their pay, prompting owner Del Webb to demand funds directly from Siegel. The project's volatile nature was punctuated by Siegel's death by an unknown shooter in June 1947, less than three months after the hotel's debut.

The very name of the resort remains a subject of historical debate. Some sources suggest Siegel chose "Flamingo" because he viewed the bird as a good-luck charm, inspired by Florida's Hialeah Park Race Track. Others argue the name was Wilkerson's, driven by his fondness for exotic birds and an interest in modeling his resort after upscale Miami Beach hotels. Regardless of the namesake, the Flamingo remains the oldest continuously operating resort on the Strip, evolving from a low-rise structure into a massive high-rise complex through decades of expansion.

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