Peripheral artery disease (PAD) compromises blood flow, often leading to the need for amputation. This case report details a 72-year-old male with a history of PAD and type 2 diabetes mellitus who underwent below-knee amputation (BKA) due to atherosclerotic limb disease. He subsequently faced complications such as wound dehiscence, prolonged wheelchair dependency, and an eventual contralateral BKA. Despite interventions including wound care and revision surgeries, persistent delayed healing underscores the complex interplay between atherosclerosis, diabetes, and wound healing. This patient’s journey highlights the critical importance of tailored management strategies and patient education in mitigating the impact of PAD-related amputations, emphasizing the need for comprehensive care to address the multifaceted challenges posed by vascular diseases.