Holley embarked upon his military career in the Occupation of the Araucanía in the Arauco War.

At the start of the War of the Pacific, he was commissioned as second in command of the regiment Esmeralda when it was created after the division of the older Carampangue in May 1879.

On 27 May 1891, Holley was named Minister of War and Navy by the Revolutionary Junta loyal to Congress established in Iquique.

[2][3] He defended the post, defeating the presidential government's forces loyal to José Manuel Balmaceda.

[4] Meanwhile, Jorge Montt, a Congressional supporter, took over control of the Santiago Government Junta on September 20.