Outlines newspaper started the first week of June 1987. Tracy Baim and most of the staff of Windy City Times left to launch Outlines after major disagreements in personality and goals. Outlines started as a weekly, then had to go monthly for many years, converting back to weekly in the late 1990s. In the summer of 1999, WCT suffered another staff walkout, and within a year was closed. A few weeks later, Outlines purchased WCT and merged into WCT that September of 2000. The next year, WCT purchased LesBiGay Radio and turned it into Windy City Radio, which ran for more than a decade, with primary host Amy Matheny.