Identifying and managing the use of medications that may be discontinued is a daunting task for the health care team, especially for the consultant pharmacist. This article discusses a framework to evaluate the risks and benefits of medications. A case-based approach will be employed to demonstrate the application of evidence-based medicine and the challenges that pharmacists face in attempting to discontinue medications in older adults. Medline and Micromedex were used as resources for primary literature as well as drug information. Studies were identified based on their relevance to the case to demonstrate the importance of applying emerging literature and evidence-based medicine. Guidelines on managing osteoporosis as well as diabetes in older adults were used for this case. A structured framework was applied to demonstrate considerations when tackling challenging medication regimens. Patient-centered, individualized medication regimens need to be developed and updated based on the needs of the patient as well as the wishes of the family and caregivers. This is a dynamic process that benefits from the consultant pharmacist, who understands the complexity of the medications and is essential to addressing the use of unnecessary medications.