Cushing’s syndrome is associated with a spectrum of systemic complications, including under-recognised effects on the musculoskeletal system. We present a case of a 37-year-old male with recurrent Cushing’s Disease who developed progressive lumbar radiculopathy secondary to severe Degenerative Disc Disease. Despite bilateral adrenalectomy, the patient exhibited persistent hypercortisolaemia and classical Cushingoid features. Imaging confirmed L4 disc herniation with nerve root compression. A multidisciplinary team initiated endocrine therapy and performed a successful minimally invasive lumbar discectomy, resulting in clinically documented neurological improvement during the immediate postoperative period. Chronic cortisol excess may disrupt spinal biomechanics and accelerate spinal degeneration through presumed bone demineralisation, muscle atrophy, altered fat distribution, and direct degradation of disc tissue. This case highlights the importance of early endocrine evaluation in patients with atypical or rapidly progressive spinal degeneration. Recognition and management of hypercortisolaemia are essential for surgical planning, optimising outcomes, and preventing recurrent spinal compromise.