Introduction: Analgesia is key to successful conservative, nonsurgical management of patients admitted to the hospital with multiple rib fractures. Recently, new fascial plane regional anesthesia techniques have become widely available. We hypothesized that since the introduction of these new regional analgesia techniques, for patients over the age of 65 years, the effect of increasing numbers of rib fractures has been mitigated. Methods: A retrospective study of patients admitted for the management of rib fractures between 2017 and 2020 was performed. Patients not admitted to the hospital, under the age of 65 years, or with chest trauma other than rib fractures were not eligible for inclusion. The primary outcome of interest was mortality. The secondary outcomes were the incidence of pneumonia and intensive care unit admission. Results were reported as the odds ratio and its 95% confidence interval and associated p-value. Statistical significance was set at (Formula presented.) < 0.05. Results: Overall, 252 patients were included and 142 patients received a regional anesthesia. The mortality rate was 4% (n = 10) with no association between mortality and number of rib fractures (p = 0.215). Twenty-four patients (9.5%) developed pneumonia during their hospital stay, again with no association with an increasing number of rib fractures. The intensive care unit admission rate was 13.1% (n = 33) and correlated with an increasing number of fractures (odds ratio = 1.15; 95% confidence interval = 1.01 to 1.31; p = 0.038). Conclusion: Management including liberal utilization of regional anesthesia for at-risk patients appears to mitigate the effect of increasing numbers of rib fractures on the incidence of mortality and pneumonia.