On Thursday morning, the New York Times broke one of those incredibly fun and insightful stories that send the political class chattering for the next week. According to reporting from Jonathan Swan, Maggie Haberman, and Shane Goldmacher:

A firm associated with the super PAC that has effectively taken over Mr. DeSantis’s presidential campaign posted online hundreds of pages of blunt advice, research memos and internal polling in early nominating states to guide the Florida governor ahead of the high-stakes Republican presidential debate next Wednesday in Milwaukee.

The trove of documents includes a debate strategy memo, internal polling from Iowa and New Hampshire, and opposition research files on most of the Republican candidates (but notably not Donald Trump). The public and the press rarely obtain this level of insight into a campaign’s strategy and research. There are tons of interesting nuggets, but what these once-secret documents do is reinforce the widely held notion that Ron DeSantis is running a miserably stupid campaign strategy; and he has no one to blame but himself and Jeff Roe, the GOP strategist pulling the strings of the whole operation.

How Did This Happen?

You are probably wondering why the DeSantis Super PAC put such sensitive documents online. Well, it happens more often than you think because our campaign finance laws are as porous as cheesecloth. Technically, political campaigns are not allowed to coordinate with Super PACs. A conference call, Zoom, or even a conversation over beers would be illegal. But they can share information by putting it in the public sphere. Sometimes they do it through the media. A campaign aide will openly discuss polling or strategy in the hopes that the Super PAC will hear it and adjust their strategy and spending. Another, even sketchier way of achieving the same outcome is to surreptitiously post information online where the campaign “stumbles” upon it. Usually these webpages are impossible for anyone outside of the intended audience to find. However, in a feat of absolute and incomprehensible incompetence, the folks at Never Back Down posted these highly sensitive documents on the main website of Axiom Strategies, the firm owned by Jeff Roe, who is ostensibly running the Super PAC.

Campaigns increasingly rely on Super PACs ever since the Supreme Court legalized corruption with the Citizens United decision. But DeSantis is trying something unprecedented.

Because his campaign is struggling to raise money, the Florida Governor offloaded a lot of typical campaign spending like polling, opposition research, and even field organizing to the Super PAC. Roe, who is supposed to be DeSantis’s campaign consigliere, actually works for the Super PAC, so he is legally prohibited from communicating with the Governor. Roe works for the Super PAC rather than the campaign for the same reason Willie Sutton robbed banks — “because that's where the money is.” Today’s New York Times story is what happens when a campaign is turned over to overly ambitious grifters.

The DeSantis Strategy

As soon as the New York Times called, the DeSantis Super PAC deleted the strategy memo that was included with the other documents. The Times reporters downloaded a copy before it was deleted and re-posted it online. Here are the four strategic priorities laid out for “GRD” — Governor Ron DeSantis:

1. Attack Joe Biden and the media 3-5 times;

2. State positive vision 2-3 times;

3. Hammer Vivek Ramaswamy in a response;

4. Defend Donald Trump in absentia in response to a Chris Christie attack.

The Super PAC is clearly concerned that DeSantis will be his boring, awkward self and spend the debate talking about DEI or some other MAGA policy priority. Therefore, the memo advises DeSantis to create viral moments like (and I’m not making this up) calling Vivek Ramaswamy “Fake Vivek” or “Vivek the Fake.”

Talk about a moment that could change the trajectory of DeSantis’s failing campaign.

A Strategy to Lose

Other than pro-forma attacks on the media and recitation of his record, Roe et al are advising DeSantis to do two things: defend Trump and hammer Vivek Ramaswamy.

The leaked internal polling shows that Ramaswamy —the 38-year-old businessman running on an “anti-woke platform — has risen in the polls at DeSantis’s expense. In April, Ramaswamy was polling at 1%. He is up to 11% in a poll conducted in early August. Over that same period, DeSantis dropped nine points.

A strategy to “Defend Trump and hammer Ramaswamy” is a strategy to come in second, and the GOP primary is neither horseshoes nor hand grenades. The core problem is that DeSantis is re-running the same failed strategy that all Republicans employed in 2016 — treat Trump with kid gloves to avoid angering his base and attack everyone, hoping to end up in a one-on-one race with Trump who then collapses under his own weight. Team DeSantis is so committed to becoming the alternative to Trump that a PowerPoint presentation on the state of the race in Iowa demonstrated their Iowa Caucus vote goal is modeled on a two-person race between DeSantis and Trump.

Team DeSantis is still operating like the potential frontrunner he was late last year and has yet to acknowledge that “GDR” is a long shot — at best. When there is a low likelihood of success, you should employ a strategy with a higher variance. In others, you take bigger risks. And you can’t be afraid to fail because failure is the most likely outcome in all scenarios.

Bet big to win big.

DeSantis is trying to win in 2024 but still maintain viability for 2028; and Jeff Roe is trying to help DeSantis while preserving his ability to make money in a world where Trump wins the primary.

All in all, it’s a plan to lose.

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