From a report at the link below:
It’s one of the questions you’re not supposed to ask in public but everyone talks about in private: What’s going on with Matt Drudge?
For conservatives, the Drudge Report was a one-stop shop for news on the Internet starting in the late 1990s. When Matt first broke the scandal involving the President of the United States and an intern, his place at the top of alternative media, as it was called then, was secured.
Matt Drudge worked the Bill Clinton - Monica Lewinsky scandal nearly non-stop to the delight of his newly found conservative readers.

Matt Drudge
The Drudge Report grew steadily until it became a leading conservative website.
As always, imitators followed. But none came close to combing as many news outlets and boiling down the essence of stories like Drudge.
That was his magic – he’d plow through stories and find the nugget buried 20 paragraphs down, then he’d rewrite the headline to reflect what the liberal outlets wanted to hide.
It wasn’t just Matt. When things blew up, he had help. Andrew Breitbart learned how to do the same by working for Drudge – a skeleton crew surfing the web, arming conservatives with the pieces of information the mainstream outlets wanted buried.
But now that has all changed. The entire tone of the Drudge Report has changed. Stories about Trump’s failures, impeachment, and Democratic talking points dominate the coverage of the president.
The Drudge report now looks more like an anti-trump hit blog, Why the change is anybody’s guess. Did Trump tweak his nose in a tweet or two about his sexual preferences?
Whatever the reason the audience that has made Matt Drudge a multimillionaire would like to know what it is. Since Drudge answers to no one, it’s unlikely we’ll ever know.
Link