Strategists and military professionals have previously questioned many of the methodological (theoretical underpinnings, the principles, and rules applied by the discipline) decisions associated with American military strategy, but the direction this essay takes is above and beyond the common methodological rivalries in how we pursue strategic desired future states. To get beyond methodological disputes entirely, we must consider thinking about our thinking as an organization on American strategy. Thus, this article hovers between philosophies, organizational theory, as well as our usually unquestioned belief in something called “strategy”. Questioning things about our basic understanding of the world tends to trigger strong organizational defense mechanisms, for good reason. Critical reflection at deep levels puts our worldview, and our role within it at stake. Nonetheless, as strategic disappointment emerges over multiple complex conflict developments, even the most cherished and guarded choices on how the world ought to work are ripe for critical inquiry. This essay examines the limited single strategic paradigm of the US defense industry and how the latest American National Security Strategy and Army Future Operating Concept (Win in a Complex World through 2030) presents a flawed strategic position. This essay presents valid alternative strategies that operate within different paradigmatic constructs.