This article assesses, by way of examples, the conduct of slave enslavement and emancipation in Santiago de Cuba in the final stage of slavery. It explores how the abolition of slavery was shaped as a necessity for the slaves themselves in need of a labour force that mitigates the technical development achieved in sugar production. In that scenario, the dilemma was the procedure to be followed in terms of defining whether abolition would be free, free of charge, full or gradual compensation. The solution was not immediate and joined the compensation and gradual formula as long as it was the least detrimental to the owners. The first step was taken with the adoption of the law on free living in 1870, the second with the so-called trustees law in 1880 and the third and final with the law on dismissal of the trustee in October 1886. These legal decisions affected two important events for the political life of Spain and Cuba, such as the Gloriosa Revolution and the War of the Ten Years, respectively; the first started in September and the second in October, both in 1868. The combination of interests between Cuba’s enslavement and Spanish political figures, as was the case of General Francisco Serrano, a regiment of the kingdom after the destronation of Isabel II, was also closely linked to the island’s sugar production.