Rates of mental illness and heavy alcohol use are exceedingly high in the legal profession, while attrition among women has also been a longstanding problem. Work overcommitment, work-family conflict, permissiveness toward alcohol in the workplace, and the likelihood of promotion are all implicated but have yet to be systematically investigated. Data were collected from 2,863 lawyers randomly sampled from the California Lawyers Association and D.C. Bar to address this knowledge gap. Findings indicated that the prevalence and severity of depression, anxiety, stress, and risky/hazardous drinking were significantly higher among women. Further, one-quarter of all women contemplated leaving the profession due to mental health concerns, compared to 17% of men. Logistic models were conducted to identify workplace factors predictive of stress, risky drinking, and contemplating leaving the profession. Overcommitment and permissiveness toward alcohol at work were associated with the highest likelihood of stress and risky drinking (relative to all other predictors) for both men and women. However, women and men differed with respect to predictors of leaving the profession due to stress or mental health. For women, work-family conflict was associated with the highest likelihood of leaving, while overcommitment was the number one predictor of leaving for men. Mental health and gender disparities are significant problems in the legal profession, clearly requiring considerable and sustained attention.