Certainly.
1) A news network that asks the hard questions is a news network that soon after dies in the ratings when politicians and CEOs refuse to be interviewed by them or come on their shows anymore. That counts doubly for demagogues. Trump gets ratings. Say what you will about Palin, she got ratings.
When Megyn Kelly moderating a Republican debate threw one hard question in with all the softballs, Trump took his marbles and went home. He refused to appear in the next Fox News debate, and its ratings were cut in half.
And so more recently Kelly “cleared the air” with Trump in an interview, asking him nothing but softball questions and laughing at his awkward jokes, embarrassing herself for the Daily Show and others to mock.
Samantha Bee, John Oliver and the Daily show are nowhere near as dependent on the good will of politicians. Often just to opposite.
2) A news network that asks the hard questions is a news network that will be accused of bias. And perceived bias is a killer for a news organization.
CNN learned to be embarrassingly pro-Bush II while he was in office. It didn’t prevent being labelled as left-wing lib’rul media elite when they had the low class to mention the occasional inconvenient fact.
For Jon Stewart on the other hand, when CNN’s Crossfire or Fox News tried to criticize him for being biased or silly, he’s say “Look, I’m a comedian not a journalist. It’s not my role to conduct hard-hitting interviews.”
3) With a hundreds more channels plus the internet, the old media simply doesn’t have the power it had.
Refusing the publicity of a televised debate would have been political suicide not long ago. But now Trump can simply tweet his message, and all the news services - old and new - will cover it.
Last year the movie Spotlight chronicled the Boston Globe’s “Spotlight” team taking on the Catholic Church over widespread and systemic child sex abuse in 2001. It’s said that the story probably couldn’t happen today. With readership WAY down, the Globe wouldn’t have had the power and legal budget to take on the church.