Aim and background: Charcot's arthropathy affecting the hindfoot (Brodsky's type 3A) and combined hindfoot–midfoot (Brodsky type 4), dilemma to fuse, hindfoot alone or hindfoot with midfoot, are not clearly defined yet. Our study aims to compare the outcomes and complications of primary hindfoot stabilization for the hindfoot alone vs combined hindfoot–midfoot Charcot's arthropathy. Materials and methods: This is a retrospective study of all the patients who were operated on for Charcot's arthropathy between 2018 and 2021. Included hindfoot and combined hindfoot–midfoot Charcot's arthropathy after trivial trauma/failed and neglected ankle fractures and excluded Brodsky's 1,2,3b,5 type—Charcot's arthropathy, nonneuropathic arthritis, inflammatory arthritis. Around N = 62 patients were grouped based on Brodsky's classification—group I (41) included hindfoot Charcot's alone (type 3A) and group II (21) included combined hindfoot and midfoot Charcot's arthropathy (type 4). Patient demographic details like age, sex, duration of symptoms (months), Brodsky classification, Eichenholtz staging, random blood sugar (RBS), glycated hemoglobin (HbA1c) at admission, diabetic status (controlled/uncontrolled), duration of diabetes mellitus (DM), duration of preoperative antibiotics, erythrocyte sedimentation rate (ESR), C-reactive protein (CRP), urea and creatinine. Radiological and functional outcomes [American Orthopaedic Foot and Ankle Society (AOFAS) hindfoot scale and Foot and Ankle Outcome Score (FAOS)] were compared between the groups. Results: Average follow-up is 19.17 ± 3.1 (months) and 19.48 ± 2.7 (months) in groups I and II. The mean age was 58.5 ± 11.05 years and 53.3 ± 11.27 in groups I and II. Male: female is 24:17 in group I and 12:9 in group II. Both the groups were similar in terms of biochemical parameters except HbA1c, which was significantly higher in group II (p = 0.003). Similarly, there was a higher number of patients with uncontrolled diabetes in group II (p = 0.010). The mean postoperative AOFAS and FAOS hindfoot scores in both groups I and II had improved significantly compared to their preoperative value (p-value group I—0.005 and group II—0.005). However, no statistical significance for AOFAS and FAOS between the groups (p-0.202 and p = 0.103). Around 67.2% of patients were able to walk unaided during the final follow-up. Tibiocalcaneal angle in both the groups during the final follow-up was statistically more significant than their preoperative value (p-value group I—0.01 and group II—0.005). However, there was an insignificant average secondary varus collapse of 4.75 ± 15.3° in group I and 5.45 ± 18.3° in group II. Around 11 of 41 (26.8%) in group I and 10 of 21 (47.6%) in group II had complications. Minor complication (superficial infection, minor implant failure (screw back-out), stable hindfoot with implant breakage)—12.2% in group I, 14.3% in group II. Major complication (deep infection, major implant failure that required nail removal/amputation, ulcer)—14.6% in group I, 33.3% in group II. Two patients needed implant removal, two required below knee amputation (BK) amputation and one plantar bony deformity required exostectomy. Conclusion: Around 67. 2% of patients with a good clinical and radiological outcome following hindfoot nailing were able to walk unassisted, and 95% of patients’ limbs were salvageable by hindfoot nailing. Patients with combined midfoot and hindfoot arthropathy were more likely to experience complications. High HbA1c is one of the significant factors that led to complications.