Background: Cushing’s disease (CD), caused by an ACTH-secreting pituitary adenoma, remains one of the most challenging endocrine disorders to diagnose and treat. The coexistence of resistant hypertension, metabolic complications, and complex vascular anatomy such as “kissing carotids” further complicates management. Case Presentation: We report a 40-year-old man with long-standing hypertension referred for evaluation of resistant blood pressure. Physical examination revealed classical Cushingoid features. Endocrine testing confirmed ACTH-dependent Cushing’s syndrome. Pituitary MRI was limited by a rare vascular variant medialized internal carotid arteries (“kissing carotids”) which obscured visualization of the adenoma. The patient underwent endoscopic transsphenoidal surgery in a specialized neurosurgical center, confirming a corticotroph adenoma. Postoperatively, cortisol levels normalized, and metabolic and cardiovascular comorbidities markedly improved. Conclusion: This case highlights the diagnostic and therapeutic complexity of ACTH-dependent Cushing’s disease with challenging pituitary anatomy. Expert multidisciplinary management remains essential to achieve remission and prevent long-term sequelae.