To get some answers, Yahoo! News tracked down Mary McNamara, the general manager at the Minneapolis office of Schubert & Hoey Outdoor Advertising, the company which owns and leases out the billboard space.
"The ad was purchased by a group of small business owners who wish to remain anonymous," McNamara said. However, McNamara did offer this political bombshell: "Some of the people in the group who paid for this were Obama supporters."
McNamara told us that the message the group hoped to convey was one of "Hope and change, where is it?" She went on to say that she has yet to receive any negative feedback about the ad, which has been up for about a month, and added that some have even contacted her office offering to donate money to keep it up.
However, not everyone is buying McNamara's portrayal of the group's ideological makeup. Cindy Erickson, the chairwoman of the Democratic Party in Chisago County, where the billboard is located, suspects the ad's funders are conservative activists posing as Obama supporters.
"I don't have any idea who did it, but my thought was that they're Tea Party people," she said. "Regardless, it's been the subject of many conversations around here."