Winnipeg is a city regarded in Canada as the city in the middle. It is, in fact, geographically at the heart of the North American Continent. It is also situated currently as a city of prevalent racism and injustice. It is also a city where there is consistent and prevalent peace work as well. It would seem Winnipeg is a city divided. Winnipeg served for thousands of years as a place for Indigenous Nations to gather, trade, and share culture. The decades and centuries that followed first contact replaced these systems with infrastructures and cultures of oppression and violence, exacting painful tolls on Indigenous Peoples and people of colour more generally. Over the last century, however, there have been social, economic, and political shifts in the city toward accepting and embracing the cultural differences it once demonized, effectively beginning the process of erecting shared cultures of peace. The purpose of the exploratory research in this study is to gauge the relative levels of positive peace or social justice in Winnipeg. To accomplish this, I drew four salient quantitative indicators from the proventive critical positive peace assessment known as the peace poles, to test their viability. To serve as a counterweight and balance to test of the measure’s saliency, representatives from four Winnipeg social organizations were undertaken to explore their ideas about positive peace in Winnipeg as the city in the middle. These four organizational representatives come from a few of the most systemically engaged organizations in the city. In this research I explored the ways in which these persons and organizations engaged in the city regarding peace, while afterward running the numbers derived from the peace poles assessment published in the Palgrave Handbook of Positive Peace in 2022. These positive peace metrics—connectivity, political voice, the gini index, and sense of belonging—only further grounded and supported the themes discovered in the interviews.