Despite a strong track record of success and parent demand, charter school growth has slowed considerably in recent years in Massachusetts and nationwide. In the Commonwealth's large urban school districts--especially Boston--this lack of growth is attributable to charter school caps that prevent the state from authorizing new charter school seats. But some school districts in the Commonwealth have room to grow. They have space available for charter expansion under the state's net school spending (NSS) cap and demand for charter schools in the form of waiting lists. A number of those districts are in Gateway Cities, "midsize urban centers that anchor regional economies around the state." The following paper provides data on the Gateway Cities with room to expand under the NSS cap. It also provides examples of how the politics of charter schooling-- both state and local--have prevented high quality operators from serving students and families who desire a charter school education. Finally, this paper concludes with recommendations to change state charter statute as well as processes and procedures related to charter school authorizing in the Commonwealth. These recommendations would make it more difficult for the state or any locality to deny families the charter school options they desire.