The shift in education reform to a goal of college and career readiness for all students is a change that has been embraced widely across the country. The challenge of designing new policies and programs that could accomplish the goal that all students should graduate from high school with the skills and knowledge necessary to succeed in college and career is tremendous. The pressing question now is whether and how students, schools, and the New York City public school system can move this ambitious goal from rhetoric to reality. To help understand this change, the challenge it presents for schools and students in New York City, and the ways in which philanthropy might help move New York City's schools closer to the goal, Philanthropy New York commissioned a set of three papers. This paper, the second in the series, examines the experiences of a single cohort of New York City public high school students who entered ninth grade in 2005, and who hoped to graduate in 2009. During this period, New York City schools showed strong improvements, and the outcomes associated with these 77,501 students were clearly representative of these positive trends. For example, graduation rates grew from 51% for students entering ninth grade in 1999 to 67.1% for the student cohort examined in this paper. However, many students in this cohort continued to encounter individual challenges and structural barriers that impeded their social and academic development, and research points to these as well. Many findings throw into stark relief historic inequities that remain major challenges today. The aim of this paper is to unify a relatively distinct--though clearly related--set of analyses into a single document to foster dialogue and advance discussions about the public schools in New York City. The following are appended: (1) Data and Analytic Methods; and (2) Multi-Level Models of Highest Math Course Completed. [For the first paper in this series, "College and Career Readiness in Context," see ED562071. For the third paper in this series, "Building Blocks for Better Schools: How the Next Mayor Can Prepare New York's Students for College and Careers," see ED562069. For the "Initiative Overview & Summary of Research," see ED562084.]