Did President Trump win a $500 million libel lawsuit against CNN? No, that's not true. The story was published by a liberal satire website that tries to mislead Trump supporters and Republicans into sharing made up stories that are clearly marked as satire when you actually click them. Articles from the site are frequently copied by foreign-run fake news websites. The people liking and sharing these stories are enriching foreign website operators or a liberal from Maine via the ad revenue generated with the content which is probably not what they expected or wanted.
The claim appeared in an article published by BustaTroll.org on May 18, 2020 titled "Trump Wins $500 Million Libel Lawsuit Against CNN" (archived here) which opened:
CNN is well-known to be a lying liberal rag of a news source. They say all sorts of mean things about our President, many of them true. This is why President Trump decided to sue them for all they're worth, for exposing him and saying horrible things.
Luckily for the American people, the Supreme Court decided in favor of the President, awarding him 500 million dollars, the largest fictitious libel lawsuit in American history. This lawsuit had no chance of losing, as it was written up by famed Constitutional attorney, Chad Benoit, who has never lost a case in his 15-year career.
The story was published under the category "Satirical Powers of an Orange President" on a page with several satire disclaimers and logos. The story also mentions a Supreme Court Justice by the name of "Joe Barron", no such Justice exists.
The site that originally published the story is part of the "America's Last Line of Defense" network of satire websites run by self-professed liberal troll Christopher Blair from Maine along with a loose confederation of friends and allies. He runs several websites and Facebook pages with visible satire disclaimers everywhere. They mostly publish made-up stories with headlines specifically created to trigger Republicans, conservatives and evangelical Christians into angrily sharing or commenting on the story on Facebook without actually reading the full article, exposing them to mockery and ridicule by fans of the sites and pages.
Every site in the network has an about page that reads (in part):
Before you complain and decide satire is synonymous with "comedy":
The use of humor, irony, exaggeration, or ridicule to expose and criticize people's stupidity or vices, particularly in the context of contemporary politics and other topical issues.
Everything on this website is fiction. It is not a lie and it is not fake news because it is not real. If you believe that it is real, you should have your head examined. Any similarities between this site's pure fantasy and actual people, places, and events are purely coincidental and all images should be considered altered and satirical. See above if you're still having an issue with that satire thing.
Articles from Blair's sites frequently get copied by "real" fake news sites who omit the satire disclaimer and other hints the stories are fake. One of the most persistent networks of such sites is run by a man from Pakistan named Kashif Shahzad Khokhar (aka "DashiKashi") who has spammed hundreds of such stolen stories into conservative and right-wing Facebook pages in order to profit from the ad revenue.
When fact checkers point this out to the people liking and sharing these copycat stories some of them get mad at the fact checkers instead of directing their anger at the foreign spammers or the liberal satire writers. Others send a polite "thank you" note, which is much appreciated.
NewsGuard, a company that uses trained journalist to rank the reliability of websites, describes bustatroll.org as:
One in a network of sites that publish false stories and hoaxes that are often mistaken for real news, run by hoax perpetrator Christopher Blair.
According to NewsGuard the site does not maintain basic standards of accuracy and accountability. Read their full assessment here.