Background: A comprehensive understanding of lifestyle (health conditions and substance use), health-related quality of life (HRQoL), flourishing (holistic representation of health), and physical activity can inform stakeholders (players, coaches, and clinicians) and help improve long-term health across the life span. Purpose: To describe health conditions (comorbidities or diagnoses), substance use, physical activity, HRQoL, and flourishing in current and former collegiate and professional baseball players and to assess the relationship between playing position and HRQoL/flourishing in former baseball players. Study Design: Descriptive epidemiology study. Methods: Eligible participants were those ≥18 years old with ≥1 season of collegiate or professional baseball experience. Participants completed a survey on health conditions (asthma, diabetes, hypertension, hypercholesterolemia, and depression), substance use (tobacco, alcohol, and energy drinks), physical activity (International Physical Activity Questionnaire–Short Form), HRQoL (Veterans Rand 12-Item Health Survey [VR-12] physical and mental component scores), and flourishing (Flourishing Scale). Adjusted multivariable regressions were performed for HRQoL and flourishing. Results: Overall, 260 baseball players opened the survey, and 214 (current players, 97; former players, 117) participated for an 82% response rate. Of the former players, 32% had hypertension or hypercholesterolemia. In addition, 26% of current players had used smokeless tobacco (median, 3 years; interquartile range [IQR], 1-5 years) as compared with 34% of former players (median, 15 years; IQR, 5-25 years). In addition, 14% of current players had used electronic cigarettes (median, 2 years; IQR, 0-4 years) as opposed to 3% of former (median, 3 years; IQR, 2-4 years). Energy drinks were consumed by 31% and 14%, respectively, of current and former players on at least a weekly basis. Current baseball players performed 8667 metabolic equivalents per week of physical activity as opposed to 3931 in former players. Pitching was associated with worse VR-12 Mental Component Scores (–5.0; 95% confidence interval, –9.0 to –1.0). Playing position was not related to VR-12 Physical Component Scores or flourishing in former baseball players. Conclusion: The similar smokeless tobacco prevalence between current and former baseball players suggests that they may start using tobacco products during baseball participation and continue after retirement. Similar reported HRQoL as compared with the general US population and high flourishing and physical activity levels suggest that baseball players may present with good musculoskeletal and psychological health.