In 1988, the Annie E. Casey Foundation launched New Futures. New Futures is a long-term initiative geared toward preparing disadvantaged urban youth for responsible and successful lives as adults. The Foundation offers grants on average of $10 million for over 5 years to five mid-sized American cities to aid in the restructuring of how these communities planned, financed, and delivered educational, health, and other services to at-risk youth. This report provided a summary of the lessons learned from the New Futures initiative. Eight lessons learned from New Futures were presented reflecting a deeper view of the difficult, complex issues New Futures sought to address by incorporating some into follow up Foundation initiatives. The lessons discussed include: (1) comprehensive reforms are very difficult; (2) it takes time; (3) it’s not for every community; (4) building local ownership is no simple matter; (5) refine and modify plans; (6) communicate; (7) real change often depends on increases in economic opportunity and social capital; and (8) stay at it.