The building originally housed six retail stores and a theater on the first floor with 20 offices and an apartment upstairs.

As a young boy, he illegally immigrated to the United States by stowing away on a ship bound for New York City.

Before he settled in Bend, Oregon, O'Kane worked as tailor, sailor, miner, stage coach driver, dispatch rider, horse trainer, and mule packer.

At the time of the Battle of the Little Bighorn, O'Kane was supporting General Alfred Terry's column, to which Lieutenant Colonel George Armstrong Custer and the 7th Cavalry were also attached.

He later managed Ed Skinner and Marley Kettleman, both world champion sprinters, taking them on a tour of Australia.

Leaving his wife to manage the hotel, O'Kane traveled around the U.S. racing horses, which he turned into a very successful business.

It was a very popular meeting place for local businessmen and civic leaders as well as a welcome stop for travelers, but on 30 August 1915, it was destroyed in a fire.

He hired the well-known Beezer Brothers architectural firm to design a fireproof building with space for retail stores and offices.

It was finished in 1916, by which time O'Kane weighed about 300 pounds; he spent most afternoons lounging in a chair propped against the building.

Because of its importance to Bend history and architecture, the building was listed on the National Register of Historic Places on 6 November 1986.

[1] The O'Kane Building is located on the west corner of Oregon Avenue and Bond Street in downtown Bend.

The offices on the second floor have large triple-window sets;[a] Above these are rectangular green tile insets with open diamond designs at both ends.

The second floor is an L-shaped corridor lined with offices along the Oregon Avenue and Bond Street sides of the building.

At the far end of the corridor overlooking Bond Street is an apartment suite originally built for the owner and his wife.