https://pjmedia.com/trending/whats-going-on-with-drudge-rasmussen-claims-matts-not-there-anymore-word-is-he-sold/
BuzzFeed reported in August that Drudge changed horses in mid-2019, hiring a new ad vendor for the first time in 20 years, leading to speculation that Matt was selling out his principles for piles of cash — hoping to expand his base by attracting left-wing readers and respect from the MSM elites. Or something. While that's possible, the site was raking in plenty of cash before the change, with revenue estimates ranging from $9 million a year to $30 million.
According to a Daily Beast report last month (citing unnamed "sources," because that's how they roll), Trump has been complaining about Drudge:
“What’s going on with Drudge?” Trump has been asking allies since Democratic lawmakers launched the impeachment probe in late September, according to a person with knowledge of his private remarks. Two other sources who’ve heard the president complain told The Daily Beast that Trump has asked those close to him why they think Drudge and his website have seemed “so anti-Trump” lately.
In recent weeks, Trump has even asked Jared Kushner, his son-in-law and a top White House official—who has had a friendly relationship with the site’s creator—to “look into it” and reach out to Drudge, the sources said.
Plausible, but is it true? Who knows, it's the left-wing Daily Beast with their unnamed sources, so take it with a grain of salt. Drudge arguably helped push Trump across the finish line in 2016, driving the media narrative and rallying the troops to get him elected, so no one would blame the president for being a little salty about the turn of events at Drudge.