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Introduction: Pneumonia-associated pleural effusion and empyema are serious complications that often require intensive care. While outcomes in pediatric and elderly patients have been studied, limited data exist on younger adults. We aimed to identify clinical and demographic predictors of ICU admission among hospitalized adults aged 20–50 years with pneumonia-associated pleural complications. Methods: We conducted a retrospective observational study of 214 adults hospitalized with pneumonia and associated pleural effusion or empyema. The primary outcome was ICU admission during hospitalization. Independent variables included empyema, alcohol use, age, sex, race/ethnicity, and comorbidity status. Comorbidity data were cleaned and grouped into “Yes” or “No,” and all categorical variables were converted to factors. A multivariable logistic regression model was used to estimate odds ratios (ORs) and 95% confidence intervals (CIs). Model calibration was assessed using the Hosmer–Lemeshow goodness-of-fit test, and multicollinearity was evaluated using variance inflation factors (VIFs). A forest plot was used to visualize the adjusted ORs. Results: Of 214 patients, 73 (34.1%) had comorbidities and 141 (65.9%) had none. ICU admission occurred in 54 patients (25.2%). In adjusted analysis, the presence of comorbidities was associated with a significantly increased odds of ICU admission (OR 2.53, 95% CI 1.28–4.99), as was increasing age (OR 1.09 per year, 95% CI 1.01–1.12). Empyema was a strong predictor of ICU admission (OR 66.66), though with wide confidence intervals due to sparse data. Alcohol use (OR 1.68, 95% CI 0.84–3.35), male sex (OR 0.97, 95% CI 0.49–1.92), and race (White or Other vs. Black) were not statistically significant. The model demonstrated good fit (Hosmer–Lemeshow p = 0.6903), and no significant multicollinearity was observed (all VIFs < 1.1). Conclusions: Among hospitalized adults with pneumonia-associated pleural effusion or empyema, comorbidities, increasing age, and empyema were independent predictors of ICU admission. These findings may inform risk stratification and resource allocation in younger adults presenting with complicated pneumonia.