Are large landowners, especially those engaged in labor-dependent agriculture, detrimental to democratization and the subsequent survival of democracy? This assumption is at the heart of both canonical and recent influential work on regime transition and durability. Using an original panel data set on the extent of labor-dependent agriculture in countries across the world since 1930, the author finds that labor-dependent agriculture was indeed historically bad for democratic stability and stunted the extension of suffrage, parliamentary independence, and free and fair elections. However, the negative influence of labor-dependent agriculture on democracy started to turn positive around the time of democracy's third wave. The dual threats of land reform and costly domestic insurgencies in that period—often with more potent consequences under dictators—plausibly prompted landowners to push for democracy with strong horizontal constraints and favorable institutions that could protect their property more reliably over the long term than could dictatorship. The shift in support for democracy by labor-dependent landowners is a major untold story of democracy's third wave and helps explain the persistent democratic deficit in many new democracies.