In 1974, Block became the first 18-year-old ever elected to office in Wisconsin, when he won a position on the Winnebago County Board of Supervisors. In the late 1970s, he worked for Republican Congressman William A. Steiger until Steiger's death in 1978, and then took a job with NCR Corporation from 1979 to 1990. Block founded several organizations including the MacIver Institute for Public Policy. Block has run and consulted on numerous campaigns in Wisconsin since the 1980s. Among others, he ran Wisconsin Governor Tommy Thompson's re-election campaign in 1990. Following the 1997 campaign of Jon P. Wilcox for the Wisconsin Supreme Court, allegations were made by the Wisconsin ElectionsBoard of election law violations. These were settled in 2001 when Block agreed to pay a $15,000 fine and not to work on any campaigns until 2004. By 2007, Block was serving as the Wisconsin director of the "pro-business" political advocacy group Americans for Prosperity. In 1997 Block was investigated by the State Elections Board of Wisconsin and agreed to a plea agreement and the payment of a $15,000 fine. In November 2012, the IRS was asked to investigate Block's Prosperity USA for spending over $40,000 of tax-exempt donations to pay for private jets, travel, and computers for Herman Cain's presidential bid. Tax-exempt charities are prohibited from intervening in the political campaign for any candidate for public office, no matter the post. CMD also asked that the IRS investigate a variety of other nonprofit groups associated with Block, including the Wisconsin Prosperity Network.
Cain campaign
Block met Herman Cain while working as Wisconsin state director for Americans for Prosperity, and both were traveling to meetings in launching branches in Ohio and Michigan. At a March 2010 dinner with Cain in Las Vegas, Block and campaign aide Linda Hansen pitched a plan for how Cain could become a legitimate contender for the 2012 Republican nomination for president. Block's rising profile in the Cain campaign gained additional attention on October 24–25, 2011, when a campaign ad showing Block smoking a cigarette caused widespread consternation and amusement. On October 30, 2011, allegations surfaced that the Cain campaign might have been illegally funded by Block's Prosperity USA. As a tax-exempt charity, Prosperity USA is not allowed to donate money or services to a political campaign. The FEC voted on January 21, 2016 to dismiss the allegations.
