In 2012, more than three million students dropped out from high school. At this pace, we will have more than 30 million Americans without a high school degree by 2022 and relatively high dropout rates among Hispanic and African American students. We have developed and analysed a data-driven mathematical model that includes multiple interacting mechanisms and estimates of parameters using data from a specifically designed survey applied to a certain group of students of a high school in Chicago to understand dynamics of dropouts. Our analysis suggests students' academic achievement is directly related to the level of parental involvement more than any other factors in our study. However, if the negative peer influence (leading to lower academic grades) increases beyond a critical value, the effect of parental involvement on the dynamics of dropouts becomes negligible.