Unknown, but perhaps September 2015 as that is the earliest date for which articles appear in its archive. The founder of the site is not identified and Wikipedia does not have an entry about Winning Democrats.com
Liberal. It takes a fairly down-the-line liberal, anti-Trump approach to most if not all topics.
Questionable. Winning Democrats does not identify its owners, administrators or writers. It has bylines on its stories but no biographical information about the authors. Most of the content seems to be generated by a robot. The site has a very cookie-cutter design. The stories are based on links to off-site stories and are rewritten to give them a liberal slant. The stories tend to be extremely short and bereft of insight. They are based on real events but are written with a strong political slant, which raises the content into question.
Winning Democrats includes ads but does not offer a paid subscription product. The site is organized into several content sections including news, politics, guns, religion, LGBT, GOP Lies, racism and healthcare. It has a page that links to video excerpts curated from other sites."