The Iowa Masons' Benevolent Society was an Oskaloosa-based life insurance company organized in 1876 that targeted the Masonic fraternal community at a time when individual life insurance policies were beyond most people's reach. Its building was constructed in two sections, with the east half built in 1883 and the west half added in 1892, so skillfully matched that many people do not notice the difference. The society merged with the Equitable Mutual Life Association of Waterloo in 1896. In 1899, the Iowa Attorney General went to court to have the entity declared operating illegally, and a judge agreed and appointed a receiver to wind up the company's affairs. In 1901, the building was sold under court order on the Mahaska County Courthouse steps for $28,200, which local papers called "a bargain." On September 4, 1912, Teddy Roosevelt, campaigning downtown under the Bull Moose Party after losing the Republican nomination to President Taft, drew community members stretching all the way to the building to hear his speech.