The aim of this study was to examine the associations between breastfeeding, asthma and mental illness in North Texas children aged two to five years, and to explore whether these associations are explained by the presence of obesity. The study population comprised of 1,174 children whose caregivers responded to a 2015 survey administered by Children’s Health and the Health & Wellness Alliance for Children. Information on breastfeeding, BMI, asthma, and mental illness were self-reported by primary caregivers. Of the 1,174 children, 61% were breastfed, 13% had asthma, and 17% had a mental illness. The odds of having asthma were 2.28 times higher among children who were obese compared to non-obese children (95% CI: 1.37-3.79; p-value= 0.001). There were no statistically significant relationships between breastfeeding, obesity, or mental health illness. Children living in a household where the caregivers had more than a college education (OR: 2.07, p-value= 0.007) or a household income of 50,000to100,000 (OR: 1.80, p-value= 0.006) were more likely to have been breastfed. Obesity was not found to be a statistically significant mediator in the relationship between breastfeeding, asthma, and mental illness. This study hopes to inform future studies about the complex relationship among breastfeeding, early childhood obesity, asthma, and mental illness