This professional report examines spatial management practices around Times Square’s many street vendors. Focusing on the contested relationship that exists between business improvement districts (BIDs) and street vendors, it situates the informal and inconsistent regulatory enforcement tactics currently used to manage street vending within the broader vending regulatory environment of the last 100 years in New York City, which has led to a largely antagonistic relationship between BIDs and street vendors. Through analysis of stakeholder focus groups, vendor interviews, observation, and pedestrian count data, it finds that many stakeholders view vendors as disruptive to circulation, maintenance, and public order, while some vendors are dissatisfied with the current regulatory scheme’s lack of clarity. In light of impending citywide vending reforms, it argues that Times Square presents an opportunity to move beyond antagonistic enforcement toward a more structured and mutually beneficial relationship between vendors and district management.