Playgrounds do not have to be static sites, but safety standards should not be the only force that guides their evolution over time. Just as the ongoing transformation of any city is a product of many interwoven factors, the collection of smaller sites that delineates one city from another should reflect the same holistic influences. This is not an argument for the abandonment of the safety standards that influence playground design. Instead, it is an argument for the adoption of and stronger adherence to community standards that influence city design. This paper argues that a park area (and more generally, any public space) that is relevant and unique to a community will be well-used by the community and, thus, a successful space; it is in a city’s best interest to create such spaces where they are lacking and protect them where they already exist. The first chapter provides a land-centric history of the growth and development of the Los Angeles region, which is especially deficient in public green space. I argue that transportation technology and infrastructure was the great shaping force of the urban environment during the 19th and 20th centuries, and discuss the Olmsted-Bartholomew “Parks, Playgrounds, and Beaches for the Los Angeles Region” report that was presented to the Los Angeles Chamber of Commerce in 1930. The second chapter covers the design communication of American playgrounds since their beginnings in the late 19th century. I also analyze the parallel between Progressive Era playground supervision and the present-day safety standard obsession that has created an equally rigid playscape. The third chapter is a case study of the ongoing historical preservation treatment of La Laguna playground at Vincent Lugo Park in San Gabriel, CA and a discussion of the value of site-specificity.