What Megyn Learned About Ron DeSantis from Having Dinner with Him That She Didn’t See on the Campaign Trail

In the wake of Gov. Ron DeSantis dropping out of the 2024 GOP primary, much is being made of where he and his campaign went wrong. One criticism has been that he didn’t connect with voters on a personal level, especially when compared to former President Donald Trump.

I had voiced similar concerns about DeSantis throughout the campaign in part because I knew the governor had the ability to loosen up. He has a sense of humor. 

When I went to interview him in Florida last summer, my team and I had a dinner with him and his wife the night before. It was off the record, but, I will tell you, he was sharing stories that had us rolling. 

There was an amazing story he told about a particular U.S. senator who went in front of Trump in the Oval Office. I am not at liberty to repeat it, but, in telling the story, DeSantis did an imitation of Trump that was among the best I’ve heard. He did it with gusto. He didn’t half-ass it. It was great. I had a smile from ear to ear and was genuinely entertained.

It got me thinking because in the law – I’m sure you’ve heard this – you hire the A students from the top schools to write the appellate briefs and you hire the C students from the second- and third-tier schools to actually get in front of a jury. It’s thought that those are the ones who were smart enough to get into law school and make it through law school but are more likely to be ‘people persons.’ 

DeSantis has had this stellar resume and career with Yale and Harvard Law School and then going right into the JAG Corps. He’s been building the presidential resume from the time he was 17, and I do think that probably makes you risk-averse. If you are not a natural ‘people person,’ your inclination would not be to press past your veneer.

You can check out Megyn’s full analysis by tuning in to episode 708 on YouTube, Apple Podcasts, or wherever you like to listen. And don’t forget that you can catch The Megyn Kelly Show live on SiriusXM’s Triumph (channel 111) weekdays from 12pm to 2pm ET.