The Days of 'Easy Radio' for Pro-Trump Hosts Like Jesse Kelly Are Ending as Midterms Approach

For conservative media personalities in the United States, boosting President Donald Trump has long been 'easy radio.' Those days are ending. As Trump enters the final two years of his presidency, rightwing hosts must prepare for life after the Trump train pulls into the station — and, more imminently, wrestle with the likely fallout of Republican losses in next month's midterm elections, and how much blame to put on an unpopular president.

Jesse Kelly is one of the most telling faces of that shift. The 6ft 8in, 45-year-old host's daily show is syndicated by radio powerhouse Premiere Networks across more than 200 stations, from 6pm to 9pm, following a three-hour block by Fox News host Sean Hannity, long an eminence grise in conservative media.

Kelly himself has said that when Trump was at his peak of popularity on the right, it was easy radio, easy podcasting and easy TV to just sit down and praise Trump all day long — that was what the audience wanted to hear.

But Kelly's warning is blunt: like any other politician, Trump cannot stay hot forever; it is not possible. The Trump era is nearing its end because his last term is almost over, Kelly says, and people are going to start looking around for the next guy.

In recent months, Kelly has gained even more attention for his willingness to criticise Trump for starting a war with Iran just months before an election he reckons will be 'rough' for Republicans. If Trump had known he would still be stuck there with $4-a-gallon gas a month before the election, Kelly said, he probably would have made a different call.

These days, any criticism of Trump from a conservative media figure prompts questions like the one a user on X recently put to him: 'Are you anti-Trump now?' Kelly is not anti-Trump — but he is prepared to upset those who are slavishly devoted to praising the president and ignoring his missteps.

Kelly's rule is simple: 'When Trump does something I don't like, I'll say it. And I'll say it when he does stuff I like.' Make no mistake, though: he still spends most of his time bashing 'commie' Democrats, referring to them on a recent show as 'sick, evil and demonic.'

While Kelly says 'a lot of people' in conservative media care about securing an invite to the White House, he claims to be uninterested in such an offer. Unless he approaches his daily show with candour and honesty, he worries listeners will think he is a phony and turn the dial.

In his assessment, a huge percentage of Trump's supporters have always understood that Trump has flaws like any other human being. The tiny percentage who worship everything he says and does are, in Kelly's words, 'generally ridiculous and stupid human beings.' The large percentage of Trump supporters, he insists, are not sheep.

Michael Harrison, founder of the talk radio-focused publication Talkers magazine, said the art of 'positioning' is an extremely important skill in the industry — one conservative hosts will need when pondering a post-Trump political world. Anyone who plans to be in radio for a very long time learns, he said, that the carpet is going to be pulled out eventually, with switching circumstances and public opinion.

Talkshow hosts on the right are all competing with each other, Harrison added: it is a game of musical chairs, and the game is changing very rapidly. Hosts have to figure out where their position is — somewhere between their own deeply held beliefs and what the audience wants. Ultimately it comes down to business: what will get ratings, clicks, views and advertising.

Kelly was an unlikely candidate to host a nationally syndicated radio show. Born in Ohio, he went to high school — and a little bit of college — in Montana before joining the marines in 2000, serving in Iraq and being honourably discharged in 2004. His rise from there to national radio host is a remarkable story.

The question now is whether a career so intertwined with Trump's rise, fall and resurrection from the political graveyard after his 2020 defeat can hold its position as the Trump era sun sets. The midterm results, and the reaction that follows, may show how this generation of conservative media figures sustains itself in a post-Trump age.