Over the last few weeks, about half a dozen reporters told me they were getting ready to write the obituary on DeSantis’s campaign and wanted to include comments I made in off-the-record meetings.
I had no intention of ever sharing these comments with the media, but seeing how they would come out anyway, I felt it necessary to get the story straight from my mouth.
For months, I warned Governor DeSantis and his team about their campaign strategy; everything from the super PAC to his message seemed wrong, and I made it known. So here’s what happened.
On May 10, I boarded a Delta Airlines flight to Tallahassee to meet the governor, his wife and his campaign team. It was a sort of meet and greet and strategy session for “influencers,” a term I despise, but I’ll go with it, given that’s what everyone was calling it. I need to clarify from the start that DeSantis, his team and the campaign did NOT pay for my hotel or flight. Every influencer had to pay their own way.
Before even getting on the flight, I was nervous for the governor. His poll numbers had declined ten points on average nationwide, and his statistical tie in Iowa had faded. Even other strong states for DeSantis, like Florida and California, were trending against him.
Making matters worse was his signing of a six-week abortion ban, which I thought was a political killer with independents who loved his decision to reopen the state quickly after Trump shut down the country. He managed to walk the line on conservative issues like immigration, Covid-19 and education, matched with a less dogmatic and more moderate approach to the environment and teachers’ wages, which helped deliver a stunning twenty-point victory in his last gubernatorial election. But the six-week abortion ban and media focus on Disney and wokeism were going to start shaving support from independents quickly.
Trump was also a huge concern of mine. Despite blowing the 2022 election by endorsing some of the worst candidates in Michigan, Arizona, Pennsylvania and Georgia and making them take a ridiculous loyalty test on whether or not the election was stolen, his numbers were starting to rebound. His army of consultants and influencers were spending months attacking DeSantis, unloading their oppo file on him, and his indictments were making him more attractive to Republican voters who felt like he was unfairly targeted.
I reached out to some influencers I knew were going to the event and said, “We need to tell him the truth. This is not going well, and this ship needs to turn around soon. Don’t fangirl, don’t be overly complimentary, just tell him what’s going on.”
Upon arriving at the venue, I immediately knew or recognized most of them. Because this was an off-the-record meeting, I will not be revealing the names of any other influencers who were there. That’s their story, and they can tell it if they want to, even though some have leaked my name to the press.
We sat in a long and sunny room in a semi-circle while senior campaign team members stood in front and around us. At the kick-off of the meeting, the team introduced themselves and gave a brief résumé of their past campaign experience. My political Spidey-sense immediately started tingling because I began to hear the same thing repeatedly: “I worked for Ted Cruz in 2016.”
I leaned over to one influencer and said, “No one here has worked on a winning presidential race.”
They started laying out the state of the race:
“Thirty percent of the Republican electorate is always Trump, 20 percent is with DeSantis, 15 percent is NeverTrump and 35 percent is like Trump but is considering an alternative who holds his opinions,” DeSantis’s pollster said.
Immediately, I thought, “No, that was the state of the race in January, but the tide is beginning to move. Trump is surging with that audience looking for an alternative.”
Their entire premise rested on a head-to-head race, where Haley, Scott, Pence and the rest of the merry bunch would drop out because of low poll numbers and dwindling money. In head-to-head competitions, DeSantis and Trump were tied in key early swing states.
They said that the super PAC was sending mailers and working on door knocking, and they emphasized that the consultants from the campaign were not getting rich from it. But it all seemed wrong; I raised my hand and asked why the super PAC was sending mailers to Democrats in South Carolina. It seemed like money was being spent quickly for no reason. Why did they have door-knockers in Texas already? It looked like the fox was minding the hen house. They assured me that the mailers were going to Democrats who’d likely vote in the Republican primary (ancestral Democrat strongholds in the South and Appalachia still have many registered Democrats but vote Republican.)
The meeting concluded, and the influencer beside me asked, “What do you think?” I looked at him and just waved my head, “No.”
We broke for a few minutes until the governor and first lady arrived. She was wearing her signature yellow, looking like Belle from Beauty and the Beast, and DeSantis made his way, saying hello to everyone. For all the talk of him being autistic or not personable, they both seemed very warm to me.
Reconvening back in the large, sunny room, I headed for the seat I had been sitting in, directly across from the governor and first lady.
They opened up the room with discussions of their agenda for Florida’s most recent legislative agenda. He gave a point-by-point rundown of the bills they passed while the first lady discussed her efforts to motivate faith leaders and religious organizations to help needy children. It was interesting, but I thought, “Is this what we came down to hear?”
Then DeSantis opened it to the floor, asking anyone for their advice before he announced his presidential run.
A social media influencer, whom I spoke to before the event about speaking honestly about the situation, started the conversation by mentioning that DeSantis did not talk enough about his working-class roots and background in the military. It was a fair critique, and DeSantis seemed open to the opinion.
Then I jumped in. For those of you who have never heard me speak, I can be fairly abrasive and value honesty more than anything.
“I read your book, and you have no national message. I mean, you talked about the traffic in Washington DC while discussing the congressional mass shooting… talk about a dad move,” I said.
Maybe not my best move to start a conversation.
“You always mention Florida, but I don’t want to move to Florida. I like mountains and seasons. You need to speak to people who want to stay in the Midwest; you need a national vision. You can’t plant palm trees in Michigan; what are you going to do for people in the Midwest.”
I doubled down. “Republican primary voters, especially white voters, feel under attack. They worry about their sons not having opportunities because of their skin color. For how smart you were and as good of a baseball player you were, you would not have gotten into Yale today because you are a straight white male. They have to know that you understand that and that you share their fears and will fight to fix it.”
DeSantis said he mentioned China, and then the next influencer began to speak. Like the first influencer, I spoke to him beforehand, saying we need to be honest that things aren’t going well, and he agreed.
But when he opened his mouth, all he did was compliment DeSantis.
I was flabbergasted.
DeSantis asked the room if voters were growing tired of hearing about Florida.
Another influencer said, “I speak to people all the time, and they are not tired of you speaking about Florida.”
It was the exact opposite of what I had just said, and I firmly believed they were wrong.
Several female influencers emphasized that it was important that Casey DeSantis appear on the campaign trail to humanize him more.
DeSantis asked the room another question, “What are the biggest issues facing the country?”
The influencer who complimented DeSantis said, “The transgender children issue is really an issue of our civilization’s survival.”
Another female influencer said, “Just nothing is working.”
More answered with a series of statements about wokeism, the trans issue and other cultural war points that made me want to scream.
“No, immigration, crime, the economy!” I yelled over everyone. “This is all you should be talking about!”
Then another influencer asked the most obvious question, “When are you announcing?”
And to my astonishment, he wouldn’t say. Top officials say they actually didn’t have a hard date. He said finishing the legislative agenda in Florida was important because voters just cast their ballot for him. I agreed with the sentiment but disagreed with the move politically.
I said, “You need to attack Trump.”
“You want me to attack Trump now?” DeSantis responded.
“Yes, do you want my phone? You can tweet from my phone.” I replied. Everyone laughed, but I was half serious.
Trump had been attacking him for half a year, and I said, “The first time you ignore it, you seem honorable; the fiftieth time, you look like a pussy.”
I sank in my chair and thought, “I said ‘pussy’ in front of Casey DeSantis, my parents would be so embarrassed.”
We wrapped the meeting and went to dinner with the senior staff, and DeSantis gifted everyone with his book, the same one that I insulted. I couldn’t get over the irony.
Looking at one senior staffer, I said, “Did I come off too harsh?”
She replied, “No, you’re fine… but no one speaks to him like that.”
I made my way to a car with another influencer. We sat in the back seat and looked at each other. He said, “Dude, that was horrible, wasn’t it? Like this is not good.” I agreed and thought I had to speak to the campaign team during the dinner.
The vibe at dinner was celebratory. People felt good, and I couldn’t understand if I was going insane. After getting a drink and some food, I sat at a table next to Generra Peck, the campaign manager. Another influencer sat on the other side of me, but after hearing much of her insight, I mostly chose to ignore her.
“So what do you think?” Generra asked me.
“I feel like we’re at an Irish funeral, waiting for the body to die,” I replied.
She was taken aback.
I said I thought her polling was off and Trump was ascending while DeSantis was declining.
Generra assured me I was wrong and showed me internal polling that the sugar high from indictment was over and DeSantis was in a statistical tie in a head-to-head competition in Iowa.
I shrugged and thought, maybe they really have this figured out. I said I’d do whatever I could to help DeSantis and left.
Weeks later, I received word that he was announcing his run on a Twitter Space with Elon Musk onstage.
While almost every other influencer said this was going to be groundbreaking, I said, “This is the stupidest fucking idea I’ve ever heard.”
Everyone who knows me from social media knows I spend too much time on Twitter Spaces. They’re glitchy, have no visual aspect and drop speakers constantly. It’s fun to spend time on but not the place for a presidential announcement. I was told endlessly that I was wrong, but unfortunately, I wasn’t. It glitched, no one could hear and people became more interested in Elon than DeSantis.
I texted Generra after the announcement that it was the worst presidential announcement in modern American political history. She didn’t respond.
As the weeks went by, I grew more frustrated. The advance team was doing a terrible job with his videos off-center with awful lighting, and he was tripling down on the Evangelical vote in Iowa. He appeared on a Christian television show, and it came off terribly to me; it took several times for DeSantis to mention he was Catholic after being asked. When asked about the Vatican, he talked about Israel. Evangelicals are not who they were in the year 2000 — many don’t go to church, most Republicans don’t go to church on a weekly basis and they’re much more transactional in how they approach politics.
In June, I received a message that there’d be an influencer call to discuss the campaign, ask any questions we had about their current strategy, and give feedback. I thought, great, maybe we can turn this around.
For nearly an hour, campaign staffers spoke among themselves while the influencers sat on mute. I became so annoyed by the whole thing I began pacing like I was preparing for a marathon.
Their conversation about strategy ended, and they said, “OK, let’s open to a question.”
An influencer asked about the best way to address misinformation on Twitter, which was a decent question. Then Generra announced, “OK, that’s all the time we had.”
I took myself off mute and firmly said, “No, I need to say something.”
After an hour of pacing and my anger growing, I went off. My voice even cracked at one point.
I said that the advance team was an embarrassment and should be fired, the messaging was all wrong, that doubling down to try to sound like an Evangelical when he was not an Evangelical would not work and his interview on the Christian show was embarrassing.
Generra insisted that I didn’t know what I was talking about, and I replied, “This is why the super PAC has nothing to work with, and they say it, you’re not discussing the issues. This is Ted Cruz 2.0.”
At that point, I was cut off by another influencer who asked the DeSantis team if they could get a hold of Elon Musk to see if he was shadowbanned.
I threw my hands up. This was not serious.
That was the last strategy call I was invited to, and while I still supported DeSantis, the writing was very much on the wall.
This article was originally published on the National Populist Newsletter, Ryan Girdusky’s Substack.