About That Tweet: DeSantis Frustrations Explained

Well, I tweeted something on Saturday and spent most of my weekend dealing with the fall out. Here’s the tweet.

Let me give my view upfront before sharing the views of others.

My view is that DeSantis has been in the race for the White House officially for less than two full months. He and his Super PAC combined have over $150 million. During his time as a candidate, DeSantis alone, without including his Super PAC, outraised Trump and Trump’s Super PAC combined on a daily basis. He is the only candidate in double digits not named Trump. The Iowa Caucuses will be on January 15, 2024. He still has time, but he does need to adjust.

The team really does need to pivot from culture war and “let me tell you what I did in Florida” to “here’s my positive vision for America,” and it needs to have a lot of pocketbook policy in it. Put bluntly, people in Ohio or Iowa do not want to be Florida, they don’t care about Florida, and they are tired of hearing about Florida. They want to know what DeSantis will do for them, particularly for their pocketbooks, which is how they perceive they will take care of their families.

I hear that pivot is coming.

I also think the campaign needs to really, honestly assess just how online it is in terms of Twitter. Kamala Harris became so Twitter oriented, her campaign focused on winning the daily Twitter fight and never made it to Iowa. The DeSantis team really dominates a lot of Twitter conversations, but that’s not actually where Republican voters spend most of their time online. It’s for the campaign to assess how much ROI they get online and if adjustments should be made. Twitter isn’t the real world and some times campaigns can forget that. Regardless of an online strategy, successful campaigns need to connect to people offline.

It is notable that there are multiple candidates in the race with national prominence, struggling with flat polling in single digits and less impressive fundraising than DeSantis, and we’re not hearing about their camps’ frustrations, concerns over viability, etc. That actually points to how many people, including those tied to other camps, see DeSantis as the contender to Trump. That’s actually a good thing for DeSantis.

That’s my view.

I also think the DeSantis team would be very, very wise to take seriously John Ellis’s critique. In short:

To be clear, Trump’s “base” is not wedded to Trump. Like every other “voting bloc,” it is open to suggestions. And it’s as transactional and pragmatic as the next constituency. Take away their Social Security and Medicare and watch your poll numbers collapse. But beneath their transactional concerns lies a code, which compels certain behaviors. And the most important of those “behaviors” are loyalty and respect.

Trump voters won’t consent to his political funeral until they hear the eulogy first. This seems obvious on its face but it’s remarkable (if not amazing) that Trump’s opponents don’t seem to understand that the first step toward defeating Trump is to honor him. Asserting that Trump is some kind of transexual pervert enabler, as a DeSantis video recently did, is so unbelievably stupid it takes your breath away.

A campaign that beats Trump is going to be one that does not attack him head-on constantly but damns him with faint praise repeatedly. He did so much good in four years, but the Democrats are doing everything they can to shackle him so he cannot cross the finish line this time. Vote for X, instead, who can carry on doing those great things without multiple indictments over X’s head and all of X’s campaign dollars going to pay the lawyers.

I would say, however, I do think some attacks on Trump, carefully done, are warranted. The Mexicans did not, in fact, pay for the wall. Trump did, in fact, support lockdowns and push Operation Warp Speed. Trump did, in fact, spend so much time with North Korea that it distracted him from dealing with China in more useful ways. He did not clean up the bureaucracy, and it was his own Department of Homeland Security that proposed drop boxes in the 2020 election. There are attacks to be made. But the basic gist of Ellis’s piece is, I think, worth considering.¹

The views of others, however, are coalescing towards one big step DeSantis must take. Before I get there, I want to note one thing.

Back in March, I flew to Vegas to talk privately with some of the biggest donors in the GOP. Most of the room was and remains pro-DeSantis. But one of them who is also a serious financial supporter of the DeSantis campaign has expressed one real concern I think is valid.

In this donor’s mind, DeSantis is the only guy with the polling and fundraising to take out Trump who, this donor believes, must be beaten because Trump can’t beat Biden. A lot of people presumed Trump was inevitable until DeSantis started to rise. But, at this point, every day DeSantis is not perceived as having some momentum in his direction is a day that someone somewhere is going to become convinced Trump really is inevitable and will act accordingly with their money, time, voice, and (for some people of prominence) endorsement. The longer DeSantis does not seem to shift momentum, the more it becomes harder to get that momentum. People want a winner, DeSantis appeared to be a winner, but doubts are growing.

I think that opinion has merit and should not be dismissed.

Now, back to the consensus view. I’m on five group chats with different people in politics — all Republican and/or conservative operatives. Though these people agree on little these days, they are in nearly unanimous agreement that Jeff Roe needs to go. Those who know the DeSantis team all have very high praise for his campaign manager, Generra Peck. But Roe is a common source of concern. They all have other, differing opinions on DeSantis and what he should do or not do or even if there is a problem, but they all agree about Roe.

Roe is the general consultant with a foot both in the Super PAC and the DeSantis team directly. He also ran Cruz’s campaign in 2016, and people in each of these group chats have said DeSantis has the feeling of Cruz 2.0, which they do not mean in a good way.

I do not really know Roe. I am in no position to judge. I would note that consultants at that level tend to make enemies as much as they make winning candidates. But this view is notable in that, again, these are chats with people in politics who know the lay of the land and the people involved, and though they agree on little, they agree on that.

This personnel issue, however, is for the DeSantis team to decide, not group chats, etc. I have no opinion on the matter, but I would do you all a disservice if I did not note the blame game is setting in with a common target. People who hate DeSantis say this is all because of DeSantis and he’s actually just not good at this. People who support DeSantis or are willing to consider him blame the consultant. That’s the nature of political campaigns generally, and it is starting to happen here.

From my vantage point, we are in early July of 2023, at a time both Jeb Bush in 2015 and Rudy Giuliani in 2007 were flying high. DeSantis has a massive war chest (but so did Jeb!) and is the only candidate polling in double digits other than Trump. DeSantis is singularly the subject of attacks from his rivals, including Trump, with a massive amount of money coming after him along with much of the press targeting him because the press, too, prefers Trump. And DeSantis is still raising money and in double digits despite all that.

So there is time.

But, there are growing frustrations, and those frustrations will begin to impact support and donations if they are not addressed. A pivot to a strong vision for the future that is not reliant on Florida is a good starting point for the campaign. A good debate performance helps too. If DeSantis cannot change the dynamic in the next month, then it may be time for a real campaign shake-up. There are 189 days until the Iowa Caucus.

The one thing I would caution the campaign is to avoid thinking external forces are going to be necessary to stop Trump. If the campaign decides Trump is really out of their hands, then their campaign’s fate is out of their hands. They should consider John Ellis’s piece and start making the case for DeSantis, not just against Trump, in different ways.

Lastly, and for all the campaigns, many people inside the GOP were hurt by Trump and those around Trump in various ways. These hurt people see the other campaigns, including DeSantis’s, as a way to settle grudges. None of the campaigns can be campaigns guided by score-settling against Trump influenced by those who feel hurt by him and his allies. The campaigns, including DeSantis’s, need to be about those candidates, not grudges against Team Trump. To the extent any campaign has people guided by animus towards Trump, the campaigns would be wise to part ways with them, lest their animosity impacts the various campaigns’ directions

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1. Put a different way, DeSantis’s campaign is the only one really in a position to take on Trump just given their money, but they still don’t seem to be able to figure out how to do it. Like the other campaigns, they seem reliant on external forces that may or may not work.