The O'Kane Building, at 115 Northwest Oregon Avenue in Bend, was built by Hugh O'Kane in 1916. Designed by the Beezer Brothers of Seattle, the O'Kane building is the best representative of early modern commercial buildings in Bend and was the first to be built with reinforced concrete. At 100 by 140 feet, with approximately 26,000 square feet of interior space, the two-story structure is still the largest commercial building in the city.

O'Kane was born in Ireland in 1857, and embarked on the first of many adventures when at twelve years old he stowed away on a ship to New York City. Over the next four decades, he was an itinerant, working as a tailor, boxer, wrestler, runner, sailor, miner, gambler, smuggler, stagecoach driver, dispatch driver, horse trainer, and sports manager. In 1895, he entered the hotelier business and built a large hotel in Grangeville, Idaho, which is no longer standing.

In 1903, O’Kane’s restlessness took him to Bend, where he built the Bend Hotel. When the hotel burned down in 1915, he immediately rebuilt on the same spot, this time constructing the O'Kane Building.  

With retail space on its first floor, the building had offices and a residential apartment on the second floor, where Hugh O’Kane and his wife lived. The main façade included stained-glass transom windows and the Bend emblem, which is still used as a symbol of the city. Decorative green tile added ornament to the storefronts. Above the main entrance was a plaster cornucopia of fruit and flowers beneath the trademark letter K, for O'Kane.

Between 1916 and 1930, the O'Kane building was the commercial heart of central—and even eastern—Oregon. The original building contained a theater, and the offices above the storefronts were rented out and used by many of the city’s prominent citizens. After Deschutes County broke away from Crook County in 1916, the O'Kane building was used temporarily as the county courthouse.

During the 1920s, O'Kane frequently sat outside his building, regaling passersby with stories of his adventures. Toward the end of his life, his restless spirit surfaced, and he left Bend for Portland, where he died in 1930.

The O'Kane Building was listed on the National Register of Historic Places in 1986. It remains in use today in much the same way it was originally intended—a commercial building at the heart of a bustling city.