Here's my favorite. Goes back to late 80s or early 90s. Sun-Times asked readers to vote for their favorite morning-drive radio personality. The winner would get a donation from the Times to the charity of their choice.

The Times probably figured that the winner would be one of the heavy hitters of that era, and the charity would be a high-profile non-profit.

Well, for reasons not entirely clear, after several weeks of balloting and counts/recounts, the winner was....an obscure morning man at WMBI. The Moody Bible station, and a home for needy kids operated by the church.