Frank Lloyd Wright's proposal for a mile-high skyscraper is rooted in the modernist vision of utilizing tall structures to enhance urban green spaces. However, commentary highlights the shortcomings of the 'tower in the park' ideology, which often results in under-activated parks that can degrade into unsafe environments. While the concept had aesthetic aspirations, its practical challenges in community engagement and safety remain contentious. There are reflections on the evolution of architectural design practices, noting the transition from hand drawings to digital design, with a nod to iconic structures such as the Burj Khalifa, which draw comparison to Wright's ambitions. Additionally, historical quotes and references to influential architectural texts like "A Pattern Language" provide context on the theoretical underpinnings and critiques of skyscraper designs.