Since the passage of the Massachusetts Education Reform Act in 1993, the Commonwealth has been seen as a national leader in education reform. The legislation introduced statewide learning standards and the Massachusetts Comprehensive Assessment System (MCAS) tests, and provided large increases in funding for K-12 education. We explore the high school experiences, post-secondary educational attainments, and labor market earnings of Massachusetts public school students since the early 2000s, when MERA was fully implemented. We highlight five key findings: 1) MCAS scores predict later outcomes; 2) educational attainments have risen over time; 3) gaps by income and race/ethnicity in four-year college completion have widened; 4) gaps in attainment exist even for students with the same MCAS scores; and 5) gaps in later earnings are much smaller for students with the same MCAS scores and attainments. Taken together, our findings suggest that the public education system in the Commonwealth has made substantial progress over the past two decades but has a long way to go in equalizing opportunities for students from key subgroups.