[6] The Enterprise was first published on November 20, 1909, and started out as a regional booster, with financial backing from Major Leigh Hill (L. H.) French.

With his backing, the paper envisioned oil wells and irrigation projects as driving a prosperous future for the region.

Stone in 1912, was credited by Enterprise publisher Arthur H. Bone with rallying public opinion behind the Warm Springs Irrigation District.

Rigby took charge of the Enterprise again until George Huntington Currey purchased it in 1917, who then traded it in 1920 for the Baker City Herald.

"[14] Thurston sold the paper in 1956 to Dudley H. Brownhill,[15] who was the son of the founder of the Californian Newspaper Publishers Association.

[20] Zaitz brought a distinguished resume, having earned widespread recognition for his coverage of the 1980 eruption of Mount St. Helens, the Rajneeshpuram community of the 1980s, and the occupation of the Malheur National Wildlife Refuge in 2016.

[26] Subsequent successful projects brought accolades and opportunities, including membership in a national local reporting network.

A man who had killed his ex-wife, and whose arrest caused another death, had previously faked insanity to avoid prison on a kidnapping charge.

[29] The Enterprise appealed to its readers for legal funds, and Zaitz told the review board that picking a fight with a small paper was like "poking a stick in a badger hole.

[38] The Enterprise ran a series of articles starting in 2019 investigating state representative Greg Smith's pursuit of economic development projects, notably the Treasure Valley Reload Center (TVRC), a rail shipping facility planned to open in Nyssa in 2020, that ultimately benefited Smith's own consulting firm.

[39][40][41] Later that year, Smith and Malheur County sheriff Brian Wolfe threatened legal action against the paper, attracting national news media attention.

"[50][51] The newspaper published a five part series on childhood poverty in Malheur County, authored by five students from the Annanberg journalism school, in 2023.