College readiness is becoming an increasingly important standard by which to measure school success and student achievement. While high school graduation and dropout prevention remain critical issues for educators, there is a substantial gap in outcomes between students who only earn a high school diploma and those who go on to obtain a college degree. For example, young adults with a bachelor's degree earn almost twice as much--and are half as likely to be unemployed--as those with only a high school diploma. Given the importance of higher education, it is decidedly problematic that students of color, especially Black and Latino males, are underrepresented among those with college degrees. For many decades, high school graduation rates in New York City lagged behind the nation, and low rates among Black and Latino students in particular were the focus of intense debate and criticism. Efforts to improve graduation rates and close gaps between subgroups of students have actually begun to pay off in recent years. Improving college readiness rates in NYC, especially for young men of color, will require a better understanding of the challenges they face--and of the levers that might serve to increase college readiness and enrollment. This report speaks to both issues by examining the trajectory of Black and Latino males on their path to college and zeroing in on points along that path where schools might effectively intervene. The report describes college-related outcomes and other indicators that help predict college readiness for Black and Latino male students over time, and discusses key contextual factors that underlie these educational outcomes. It then uses this research to inform the Expanded Success Initiative (ESI), an ongoing citywide effort to improve college and career readiness for young men of color, which the Research Alliance is evaluating.