As a child, his family moved to Königsberg, Kingdom of Prussia, where he learned German, business, and military strategy in school.

[1] Roloff served in the Union Army during the American Civil War in the 9th Ohio Infantry Regiment, working under the command of August Willich.

[2] That same year he traveled to Cuba after being hired by Bishop and Company,[3] an American[4] sugar-exporting firm in Caibarién, Las Villas Province, as a bookkeeper.

He was a founder of the San Juan Masonic Lodge in 1866 and was treasurer of the El Progreso Social Club, gaining a local reputation for his success in the position.

As the majority of members were strictly civilian they sought out a military leader and when confronted, Roloff accepted, joining on the evening of 6 February.

Miguel Jerónimo Gutiérrez named sugar mill owner Joaquín Morales as commander-in-chief and Roloff as major-general and chief-of-staff in Las Villas.

So, as Commander- in-Chief, I really don't have much to do, because Roloff will [militarily] do everything.On 7 February, carrying a Cuban flag,[a] around 5,000 poorly equipped Villareños[b] traveled from the coffee plantation to Manicaragua.

On 17 February, Roloff led 100 men in an attempt to take Santo Domingo, failing due to low ammunition.

On 6 March, three regiments totaling 800 men led by provincial governor, Trillo Figueroa, lost at Santa Cruz del Líbano.

Roloff suggested a scorched earth campaign in the sugar-rich west to gain freedmen volunteers and to harm the colonial economy.

The proposal was rejected citing a lack of resources; it was decided they move to the Oriente Province to receive supplies from Céspedes.

During their march, Roloff's forces sabotaged bridges, telegraph poles, railways, and burned sugar plantations.

Commander-in-chief Ignacio Agromente's death on 11 May 1873, vitalized a power vacuum and greater division between the House of Representatives and Céspedes.

He gave Roloff command of the Second Division and ordered him to attack Sagua La Grande, falsely claimed to be holding a Spanish garrison.

In the following months, Villareño forces gradually surrendered as they faced against the Spanish commander in the region who received 60,000 pesos until ordered to stop by the Cuban Patriotic Junta in April.

To support García and other patriots participating in the Little War, Roloff went to the Colony of Jamaica in March 1880 to raise funds, though the conflict ended in failure by August.

Roloff remained in Jamaica with fellow veterans of the Ten Years' War, Antonio Maceo and Máximo Gómez, until late 1881, before he left to Amapala, Honduras to work at the town's central bank.

[17] He was designated vice consul by the United States government and entered the country with Dr. Eusebio Hernández Pérez at Puerto Cortés.

[19] In 1892, he returned to the United States answering, along with other veterans of the Ten Years' War, José Martí for a new plan to achieve Cuban independence.

[16] After Martí funded newspaper, Patria, reported:[20] Tampa salutes Roloff, the hero who fought day and night for ten years for the freedom of a land which was not his.

Today he is received with admiration by everyone and everyone seeks to shake his hand and express love and admiration for this son of Poland, who today is our honored guest in Tampa.He responded with a speech advocating for the party:[20] [...] the Cuban Revolutionary Party is the entity with which your support will once and for all, end the Spanish government's tyranny in Cuba.

He also led the Lotería de la Patria, which ran from August 1894 to March 1895 and raised thousands of dollars for the party.

The New York World reported that Martí was seen in Fernandina, which prompted Spanish ambassador Emilio de Muruaga to claim U.S. violation of national neutrality laws and requested an investigation.