Many who attempt district-charter collaboration point to "politics" as a constraint that affects their work, but little is understood about why some collaborations enjoy broad support while others become mired in conflict. Drawing upon CRPE's multiyear study of district-charter collaborations in dozens of cities as well as research on other cross-sector initiatives, this report explores how politics shapes collaboration and offers strategies to help education leaders improve their chances of success. The report finds: (1) District-charter collaborations are inherently political. These efforts can succeed only if both sides see it to their advantage to work together; (2) Not all cities are well poised politically for collaboration. Declining enrollment, a weak charter sector, and unfavorable community politics can undermine district-charter work on common goals and (3) Mutual wins and shared values may offer a sweet spot where collaboration can take root. District-charter collaborations have been more likely to find success when the sectors found it in their interests to work together, not because either made a one-sided sacrifice.