After the death of Juan Bautista Gill in 1877, he helped ensure his friend Cándido Barreiro gained the presidency. Soon after Barreiro's death he organised a coup and took the presidency for himself, during which period he privatised much of the land in Paraguay to raise money.
Caballero rigged the 1886 election to ensure the victory Patricio Escobar, his favoured candidate. In response, his opponents founded the Liberal Party and he then founded the Colorado Party. Out of office, Caballero maintained a large degree of control as he remained commander of the army. His favoured candidates controlled the country until 1894, when Juan Bautista Eguzquiza overthrew Juan Gualberto González. Caballero helped to organise another coup in 1902, putting Juan Antonio Escurra in power, but after Escurra's overthrow by the Argentinean Army, the Liberals took power.
The Paraguayan town of General Bernadino Caballero is named for him.
Caballero rigged the 1886 election to ensure the victory Patricio Escobar, his favoured candidate.
Caballero helped to organise another coup in 1902, putting Juan Antonio Escurra in power, but after Escurra's overthrow by the Argentine Army, the Liberals took power.