Background: The 2019 Center for Disease Control and Prevention’s Core Elements of Hospital Antibiotic Stewardship identifies community-acquired pneumonia (CAP) as a crucial area for improving antibiotic use. Transitions of care (TOC) pharmacists can optimize medication therapy for CAP patients. Methods: This was a retrospective, multi-hospital analysis of discharge antibiotic prescribing. Between December 1, 2022, and June 30, 2023, TOC pharmacists intervened to decrease discharge days of therapy (DOT) for CAP therapy. The study compared records of CAP patients with a TOC antibiotic stewardship intervention vs those without. An additional three-group analysis compared patients without an intervention to those with an accepted intervention to those with a rejected intervention. Results: 196 patient records were included in the analysis; 80 had a TOC pharmacist intervention and 116 did not. 62 interventions were accepted and 18 were rejected. Mean final discharge DOT was 3.8 ± 1.7 days in the non-intervention group and 3.4 ± 1.6 days in the intervention group (P = 0.231). Mean total DOT was 6.8 ± 2.3 days and 6.8 ± 1.8 days, respectively (P = 0.963). The percentage of patients with appropriate total DOT was 59.5% and 66.3%, respectively (P = 0.337). In the three-group analysis, mean final discharge DOT was 2.9 ± 1.7 days in the accepted group and 4.2 ± 0.9 days in the rejected group (P = 0.030). Mean total DOT was 6.4 ± 1.6 days and 8.1 ± 1.8 days, respectively (P = 0.009). The percentage of patients with appropriate total DOT was 82.3% and 11.1%, respectively (P < 0.001). Conclusion: The accepted TOC pharmacist interventions significantly reduced both discharge DOT and total DOT. These findings emphasize the impact TOC pharmacists can have with antimicrobial stewardship initiatives.