Population ageing and improved survival after cardiovascular interventions have led to a growing number of elderly, multimorbid patients with complex valvular heart disease (VHD). In particular, structural degeneration of aortic bioprostheses has become an increasingly frequent cause of severe valvular dysfunction and heart failure (HF) in patients with a high burden of comorbidities and previous cardiac surgery. In this complex population, a patient-centred, Heart Team–based approach, integrating clinical status, multimorbidity, frailty, advanced imaging, and life expectancy, is pivotal in guiding therapeutic decision-making. We report the case of an 84-year-old man admitted with signs and symptoms of HF. His medical history included diabetes, hypertension, dyslipidaemia and chronic kidney disease. In 2016, he underwent coronary artery bypass grafting (LIMA to LAD, SVG to RCA) and surgical aortic valve replacement with a Sorin Crown N. 23 bioprosthesis for angina and severe aortic stenosis. The echocardiogram revealed a severe aortic prosthetic regurgitation, a moderately reduced left ventricular ejection fraction(EF) (48%), and a markedly increased pulmonary artery systolic pressure (73 mmHg). NT-proBNP level was 2185 pg/mL. Despite optimisation of medical therapy, the patient’s clinical condition did not improve. Although the STS score was 7.8% (intermediate risk), the clinical profile was consistent with the “high clinical complexity” category defined by the 2025 ESC/EACTS Guidelines, in which surgical risk scores may underestimate overall risk and decision-making should be Heart Team–driven. The patient therefore underwent urgent valve-in-valve TAVI with implantation of a 23-mm Evolut FX prosthesis. The post-procedural course was complicated by delirium, an episode of atrial fibrillation, and difficulty in weaning from inotropic support, resulting in a prolonged hospital stay. At 12-month follow-up, the patient showed significant clinical and echocardiographic improvement and improved left ventricular function (EF 60%), reduced pulmonary pressures (sPAP 40 mmHg), and stable prosthetic valve function. This case highlights the growing clinical challenge of managing highly complex conditions in elderly, multimorbid patients, particularly in the presence of previous cardiac surgery. A comprehensive and individualised Heart Team approach is essential to balance procedural risk, comorbidities, and expected clinical benefit.