The O’Kane Building is shown at its completion. (Des Chutes Historical Museum/Submitted photo)

In his time, Hugh O’Kane might have been considered the most interesting man in the world.

Or at least in Oregon.

The 300-pound Irish entrepreneur would famously sit in his big rocking chair in the old Bend Hotel, which he built in 1905, and tell stories of his many adventures.

As a young boy, O’Kane left his home in Ireland and rambled around England, Portugal and Spain as a stowaway. He boarded a ship one day with other boys, not realizing they were heading to New York. At 12 he started a new life in New York as a fabric cutter and newsboy.

“Still restless, O’Kane, with several lads about his own age, stowed away again at Liverpool. Thoughtless of any destination, the boys woke up one morning in New York harbor,” according to an account in The Bulletin.

Adventures continued as he moved west across the United States. O’Kane carried dispatches and provisions for the U.S. Army in North Dakota and Montana during conflicts with the Sioux.

A former lightweight boxer and wrestler, O’Kane later managed Tom Cannon, a world champion Greco-Roman wrestler in 1881. O’Kane also loved horses and co-owned a horse named Spokane, which won the Kentucky Derby in 1889.

All of these experiences happened before O’Kane called Bend home.

“His life was replete with adventure and, if written, would be a biography of absorbing interest,” read The Oregonian on Feb. 18, 1930, two days after O’Kane died in Portland.

O’Kane was drawn to Bend in 1903 by the potential of profitable lumber mills. The next year, he moved to Bend with his wife, Helen.

The Bend Hotel burned down 10 years after O’Kane built it, but he then built the concrete O’Kane Building at the same location on Bond Street and Oregon Avenue in downtown Bend.

The building is now listed on the National Register of Historic Places.

The O’Kanes lived on the second floor of the building. In 1925, they built a house at the corner of Louisiana Avenue and Broadway Street.

“Many people remember Hugh sitting in front of the main entrance to his office and retail building in a big rocking chair. After he moved out of it, he walked to the sidewalk ‘office’ every workday to sit and talk to his friends,” according to a written account at the Des Chutes Historical Museum.

When his health started to fail, O’Kane and his wife decided to move to Portland. He was 73 when he died there. Helen died five years later at 65 years old.

Throughout O’Kane’s life, many could not believe the stories he told.

“So many and remarkable were the experiences of Hugh O’Kane in the days when the West was wild and in distant places, that many doubted them, but he was always prepared to give dates and locations and prove his statements,” read the 1930 Oregonian article.

— Reporter: 541-617-7820,

kspurr@bendbulletin.com