The Downtown Community Safety Partnership (DCSP) is an outreach organization dedicated to enhancing safety and wellness in downtown Winnipeg. As a unique initiative combining outreach patrollers with long-term case management services, scarce research exists regarding how organizations like DCSP operate or their impact on the community. Additionally, cities often lack knowledge on how such organizations allocate funding to achieve their intended outcomes. This thesis examines two key questions: (1) Was DCSP implemented as planned? and (2) Does DCSP achieve its goals? Four research methods were employed to answer these questions: quantitative analysis, qualitative interviews, literature review, and field observations. Overall, DCSP was implemented as planned. Although qualitative interviews show Winnipeg safety personnel believe DCSP is positively impacting Winnipeg, quantitative analysis did not reveal any major effects. This research provides insight into DCSP’s operations and effects and provides a baseline for subsequent evaluations. The conclusion presents twelve recommendations for DCSP.