Each year, more than 55,000 students graduate from the public high schools run by the New York City Department of Education (DOE); 58,000 did so in school year 2019-20. In percentage terms, the city's cohort graduation rate--that is, the percentage of entering ninth-graders who graduated within four years--has increased steadily from the early 2000s and now stands at 78.8%. However, the meaning, or value, of a high school diploma has been debated during the two decades that the city's graduation rate increased. Meanwhile there is a more fundamental question: "Should" a high school diploma, of any type, signify college readiness? More generally, is enrollment in an academic course of study in college the "only" appropriate goal for high school graduates? This paper considers these fundamental questions by examining the academic standing of NYC DOE high school graduates (that is, district public schools, not private or public charter high schools) who enter associate's degree programs in the City University of New York (CUNY), as well as the measurable outcomes, retention, and graduation rates of its colleges. It is based on publicly available aggregate data maintained by the city's DOE and CUNY's Office of Institutional Research.