The grid plays a prominent role in architecture, aiding in space organization and influencing all aspects of planning, ranging from urban design to intricate building details. This paper posits that the grid receives heightened emphasis in Brutalism, particularly in constructivist Brutalism, where materials and construction are intentionally exposed. A question arises regarding the grid’s characteristics—despite its subtle appearance, the grid can sometimes be deceptive, ambiguous, and manipulative. The paper analyzes the merits and drawbacks of employing the grid in architecture, shedding light on its contributions to both structural and perceptual comprehensibility, as well as its role in increasing usefulness. To illustrate the application and perception of the grid, the paper examines two primary planning levels: urban planning and building design. The case studies focus on examples from New York City housing developments, specifically those constructed between the 1950s and the 1970s, and projects by architect I. M. Pei, which offer valuable insights into practical implementation. The paper concludes that while the grid can establish order, it may also engender an “uncanny” feeling.