In the wake of Cuba's far‐reaching, halting economic reforms, geopolitical rapprochement and trade openings with the United States (US) offer opportunities and risks for Cuban small‐scale farmers and agrarian cooperatives: pressures, paradoxes and potential abound. Meanwhile, on the margins, agro‐ecologically oriented tours bring admiring US students, farmers and agrarian advocates. Cubans concur that the country must solve key problems in its agricultural sector to overcome the contradictions of its agri‐food model, and that this entails more exchange with the US – but in what capacity and on what terms? The current crossroads begs the classic agrarian question, even as it updates it. Having experienced and survived the promises and disasters of both capitalist and communist agricultural economies, Cuban farmers expand the original ‘peasant’ protagonist. As they navigate new non‐state markets and recent re‐entrenchment of state control of prices, Cuban farmers and cooperatives struggle to avoid monopolizing tendencies of unfettered capitalist as well as communist agricultural economies – both of which have historically been ecologically damaging. US agribusiness courts Cuba, but not as mere unidirectional capture: Cubans are inviting and leveraging trade to end the embargo, which is increasingly being modified altogether. Key Cuban agrarian principles of resilience and cooperativismo have persisted through capitalist and communist crises: could they influence prospects for agro‐industrial hegemony from the North?