The American healthcare payment model introduced Pharmacy Benefit Managers (PBMs) into a position of power that currently puts into question the state of the pharmacy profession, especially in the community field. Reimbursement plans had been designed to benefit all stakeholders and save patients money but have only been shown to increase costs for these involved parties. There exist unresolved gaps in care as a result of the healthcare structure and underutilized skills of trained pharmacists who do not have the federal means to provide clinical services. Four collaborative payment models have been proposed, offering methods to quell the monetary problems that exist and are predicted to continue with the closure of community pharmacies and sustained influence of PBMs. These models may additionally allow the expansion of pharmacy career paths and improve healthcare benefits for patients. With a reflective perspective on the healthcare structure and knowledge of positive impacts with the inclusion of pharmacists, solutions to payment challenges could present a progressive approach to an outdated system. The impact of the COVID-19 pandemic highlights a dependency on pharmacists and community settings. This outlook on pharmacists may persist and an established expansion of services could prove beneficial to all healthcare stakeholders.