Between 1900 and 1910, Glendive’s population doubled to 2,448 and the small settlement had begun its transformation from a one-stop cowtown to a more sophisticated city, where residents could stroll on cement sidewalks and tap into a brand-new water system. Charles Krug, a prominent local rancher and businessman, built this investment property in 1910 as Glendive stood on the brink of its greatest prosperity. The Glendive Independent reported in October of that year that a new drug store, “modern in all respects,” would occupy one of the nine commercial spaces that realtor George Beasley had leased from Krug. Brick and concrete document the additions which, by 1929, extended along the back of the building. Tenants included a jeweler, a tailor, and a milliner as well as a restaurant, a drug store, and a variety store. Newer brick, doors, and windows have modernized its appearance, but the block is significant today for its long association with the Krug family and as a representative of this prosperous era.