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West-Side Railroads, Samuel A. Clarke and Joseph Gaston, should both afterwards write histories of Oregon.

His three years as a railroad executive were preceded and followed by editorial positions. For a year, in 1864–65, he was editor of the Oregonian. He stepped out to join the Oregon and California Company; a young man by the name of Harvey W. Scott who had been contributing pieces to the paper and acting as city librarian and studying law, stepped into the place and became famous. He took his portion of the Ben Holladay purchase money and bought the Salem Statesman, which had been renamed the Unionist after Sam. L. Simpson's father had sold it. He gave it back its old name and edited it for three years until 1872. He then bought, in partnership with D. W. Craig, the Willamette Farmer, which he ran until 1878, when he moved to Portland to serve as head of the literary bureau of the Villard railroad syndicate until Villard's failure in 1883.

In 1884 he shipped the first car of cured prunes from the Pacific Northwest.

He devoted the next two years to research and writing, another literary period that met with final frustration, as described in the Oregon Native Son:

The years 1885–6 he devoted to historical work that was published in the Oregonian as Pioneer Days. He gathered material from fur trader, mountaineer, Hudson Bay sources, missionaries and the earliest pioneers, many of whom he knew. He hoped to devote his life to a continuance of this work, but ill health and the death of his wife, who was his life's inspiration, as well as his assistant, prevented. Overwork had caused nervous prostration that lasted for years,