Background: Left ventricular assist devices (LVADs) are an established therapy for advanced heart failure, yet long-term outcomes remain heterogeneous. Identifying the main predictors of mortality, heart transplantation, and hospitalization is essential to improve post-implant management. Methods: We conducted a single-center, retrospective observational study including adult patients who underwent LVAD implantation between 2014 and 2024. Clinical, echocardiographic, laboratory, device-related, and pharmacological data were collected from electronic medical records and follow-up visits. Prognostic associations with mortality, heart transplantation, hospitalizations, and right heart failure (RHF) were evaluated using univariate and multivariate analyses. Results: Thirty-one patients (median age 65 years, 93.5% male) were included. Baseline comorbidities and INTERMACS class were not predictive of adverse outcomes. In contrast, chronic kidney disease at implantation emerged as a strong predictor of mortality, heart failure–related hospitalizations, and arrhythmic events. Moderate-to-severe post-implant aortic insufficiency was significantly associated with reduced survival, worse functional status, and increased likelihood of heart transplantation, indicating LVAD failure. Post-implant right ventricular dysfunction was the strongest prognostic determinant: reduced right ventricular fractional area change (RVFAC) predicted late RHF, which showed robust associations with mortality and cardiovascular hospitalizations. Among medical therapies, RAAS inhibition was associated with left ventricular reverse remodeling and fewer hospitalizations, while SGLT2 inhibitors correlated with improved functional status. Levosimendan use was strongly associated with late RHF and heart transplantation, reflecting severe hemodynamic instability. Conclusions: In LVAD recipients, long-term outcomes are primarily driven by post-implant right ventricular failure, renal dysfunction, and development of significant aortic insufficiency rather than baseline comorbid burden. Late RHF and severe aortic insufficiency represent the most powerful predictors of death and need for transplantation, highlighting the importance of dynamic risk stratification and targeted post-implant management.