Background: Intertrochanteric hip fractures are among the most common and most expensive diagnoses in the Medicare population. Liposomal bupivacaine is a novel preparation of a commonly used analgesic agent that, when used intraoperatively, decreases narcotic requirements and hospital length of stay and increases the likelihood of discharge to home. The purpose of this investigation was to determine whether there was an economic benefit to utilizing intraoperative liposomal bupivacaine in patients with fragility intertrochanteric hip fractures in comparison to a group of patients who did not receive liposomal bupivacaine. Methods: This is a retrospective observational study performed at two academic medical centers. Fifty-six patients with intertrochanteric hip fractures treated with cephalomedullary nail implant who received standard hip fracture pain management protocol were compared to a cohort of 46 patients with intertrochanteric hip fractures who received additional intraoperative injections of liposomal bupivacaine. All other standards of care were identical. A cost analysis was completed including the cost of liposomal bupivacaine, operating room costs, and discharge destination. Statistical significance was set at p < 0.05. Results: Although the length of hospital stay was similar between the two groups (3.2 days vs. 3.8 days, p = 0.08), patients receiving intraoperative liposomal bupivacaine had a lower likelihood of discharge to a skilled nursing facility (84.8% vs. 96.4%, p = 0.002) and a longer operative time (73.4 minutes vs 67.2 minutes, p = 0.004). The cost-benefit analysis indicated that for an investment of $334.18 in the administration of 266 mg of liposomal bupivacaine, there was a relative saving of $1,323.21 compared to the control group. The benefit-cost ratio was 3.95, indicating a $3.95 benefit for each $1 spent in liposomal bupivacaine. Conclusions Despite the increased initial cost, intraoperative use of liposomal bupivacaine was found to be a cost-effective intervention due to the higher likelihood of discharge to home during the postoperative management of patients with intertrochanteric hip fractures.