Background: The purpose of the study was to evaluate the suitability of reverse total shoulder arthroplasty (RTSA) with a cementless and metaphyseal stem fixation as a treatment for complex proximal humeral fractures (PHFs) with a calcar fragment when this may be fixed with a steel wire cerclage. Clinical and radiographic outcomes were compared with the same RTSA for PHFs without a calcar fragment at a minimum of five-year follow-up. Methods: A retrospective analysis was performed on acute PHFs “with a medial calcar fragment” (group A) and “without a calcar fragment” (group B) treated with a RTSA and cementless metaphyseal stem fixation. Results: At an average follow-up of 6.7 years (5–7.8 years), no statistical difference was observed comparing group A (18 patients) to group B (50 patients) for active anterior elevation (141 ± 15° vs. 145 ± 10°, p = 0.67), active external rotation ER1 (49 ± 15° vs. 53 ± 13°, p = 0.55), and active internal rotation (5 ± 2 vs. 6 ± 2, p = 0.97). Similarly, a comparison of ASES score (89.2 ± 10 vs. 91.6 ± 9, p = 0.23) and Simple Shoulder Test score (91.1 ± 11 vs. 90.4 ± 10, p = 0.49) revealed no significant difference. Conclusion: RTSA with a cementless and metaphyseal stem fixation represents a safe and feasible treatment for complex PHFs with a medial calcar fragment when this may be fixed with a steel wire cerclage.