Why Some 2024 Hopefuls Should Have a Talk With Jeb Bush

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Both Mike Pence and Chris Christie are set to jump into the 2024 race next week, joining Ron DeSantis in vying for the role of leading Republican not named Donald Trump. It goes without saying that all three men are hoping to not end up the Jeb! of 2024. Anything but that!

And yet, each member of the trio appears to be taking a distinctly Jeb!-ian approach to funding and running his campaign, despite the questionable track record when contenders have adopted such a tactic.

The plan seemed like a smart one back in 2015, at least at its inception. Rather than have the former Florida Governor chase headlines or start to chop at his 2016 rivals, he held off on all of that while Bush’s Miami headquarters focused on one thing and one alone: picking up massive checks to seed a nominally separate super PAC. To bide time, Bush would filibuster when asked about politics: “10-yard penalty, loss of down,” he would tell reporters when we asked about news of the day.

The thinking was rational. Eventually, when things got rough, the super PAC and its unmatched resources could build a wall of sorts around the bookish Bush, who could meanwhile run the campaign of his own making, one focused on footnotes, wonks, and actual deliverables.

Among the biggest problems in this thesis: Jeb! Inc. had not anticipated the dominance of Trump, against whom no amount of super PAC spending or fact-based logic could matter. The other big problem: The more voters got to know Bush, the worse he did. He was the Cousin Greg of 2016. It was as clear an example as exists in the super PAC era about the limits of money and its proximity to truly reorient the political environment—and one that many of the 2024 contenders these days are loath to learn.

In Iowa, where Trump spoke at a Fox News town hall Thursday evening, DeSantis and his super PAC are working to plant seeds of doubt about Trump’s true conservatism. Pence and Christie are both readying announcements next week now that they have similar deep-pocketed fixers watching over them.

Those outside super PACs, nominally independent and legally barred from coordinating strategy with the candidate or his official team, are still seen as heaven-sent answers to fundraising challenges. Because super PACs can legally accept unlimited—and often ungodly—sums of money, they are perceived as a way to keep the candidates focused on the things that only candidates can do, like headline events, make policy speeches, and answer voters’ questions directly. The super PAC, the thinking goes, can handle the routine things that voters only passively notice, like advertising, polling, voter-registration and get-out-the-vote operations. And from the looks of it, both Pence and Christie are going to lean heavily on their super PACs to do a good chunk of the skullduggery that is campaign infrastructure.

It’s a tempting proposition, but one that has never proven terribly successful. In fact, only Barack Obama’s 2012 victory stands as an example of a super PAC really making a difference in the race, having spent $66 million on negative ads against Mitt Romney. Hillary Clinton’s use of the Democratic Party’s primary super PACs in 2016 proved insufficient and too narrowly focused on hitting Trump, whose image never seemed to flake; Joe Biden’s outside pals at the same group raised about one-quarter less in 2020 than in 2016 to focus almost exclusively on digital advertising in an environment teed up for Biden.

As much as super PACs are heralded as a financial answer for candidates, they are often a source of troubles. They breed competition for donors, build confusion in voters’ minds, spark conflicts between competing camps that ostensibly back the same candidates, and feed terrible inefficiencies. They can create their own legal woes. If done poorly—as is commonly the case—the super PAC builds a shadow campaign in duplicate.

Because super PACs have unchecked ability to raise money, they often have far more lax checks on spending. To sketch a specific case for the uninitiated, that consultant’s $25,000 bill can be covered by one super PAC call to a sugar daddy while a campaign would have to find eight brand new donors who haven’t opened their checkbooks and are willing to max-out their contributions, right?

In practice, it gets even tougher. The donors who max-out with $3,300 checks to candidates are rare; roughly two-thirds of Biden’s fundraising in 2020 came in increments under $200, while less than one-fifth came in chunks of $2,000 or more. It seems a lot easier for a candidate’s loose orbit to collect checks in huge sums, but there are huge complications incumbent in that system once the money comes across the table.

All of this, of course, is limited to the official super PAC spending. In campaign finance circles, so-called “dark money” groups also are operating. Unlike super PACs, which have to disclose their donors in regular reports to the Federal Elections Commission, the “dark money” operators are technically organized under the tax code as social-service or nonprofit groups that can hide their patrons. A must-read New York Times analysis of the top 15 Democratic-aligned nonprofits spent more than $1.5 billion in 2020 to the $900 million unleashed by the top 15 GOP-aligned nonprofits. (For the sake of a comparison, Biden’s official effort that year raised $1 billion and Trump pulled in $810 million. The median household income last year was about $71,000.)

Yes, these are absolutely insane sums of money in politics. In a time not that long ago, general election campaigns ran on a public financing system that ensured ideas, not checkbooks, fueled the presidential campaigns. George W. Bush and John Kerry each had about $150 million in public financing to run their post-nominating convention march to Election Day 2004.

Fast-forward a little more than a decade. The pro-Jeb Bush super PAC Right to Rise wrangled $118 million and spent $87 million on advertising—a line-item that was almost triple the official campaign’s total budget. And yet, it turns out, for all the hyping of the super PAC strategy, it didn’t matter. Bush finished sixth in lead-off Iowa, ended up fourth in New Hampshire and South Carolina alike, and flew home from Columbia, S.C., as a former candidate.

Even Bush himself was frustrated with the super PAC’s work, asking a Des Moines Register reporter trailing him for a day in January 2016 who was behind billboards publishing Bush’s own words. “What the hell is that?” he asked. “Is that Right to Rise?” As the campaign got closer to counting voting, the pro-Bush donors were in open revolt about the efficacy of spending, including a 15-minute documentary on New England Sports Network that seemed more suited for Pyongyang than Portsmouth, N.H. Outside his events, you could differentiate the campaign signs from those planted by the Super PAC by punctuation: the ones with Jeb branding were from the super PAC, and the ones with Jeb! came from the campaign. Bush didn’t seem fully comfortable with the super PAC by the end. “It’s a weird system where you’re, you know, you can’t have any coordination,” he said.

As I chased Bush around the fields of Iowa, the wedding halls of New Hampshire, and the convention centers of South Carolina, it was like watching a candidate that seemed unable to look around and see Trump had changed the rules, perhaps permanently and most likely not for good. Writing from his extremely deflated—and, as time marched on, increasingly drunk—campaign headquarters on the night he ended a White House march plotted for years, I posited that Bush’s problem was he was running in “a year that saw bluster overtake substance, and Bush refused to shift.” He was merely an early canary in the coal mine that America would become.

“You cannot insult your way to the presidency,” Bush repeated time and again. He believed it. Well, it turns out Trump could. He did. And no one has proven that his talent for cruelty has abated—or that any amount of money on its own can dent his standing, be it from a donor to a candidate or a super PAC.

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