Inside the political fundraising machine that is flooding your inbox

If you feel like more and weirder political fundraising emails are clogging your inbox, you’re right.

Campaigns at all levels of government have been feverishly pumping out these messages. With less than a week to go before the midterm elections, it’s reached a fever pitch, digital strategists and marketers who have worked with campaigns told Grid. The subject lines plead, cajole or even try to scare recipients into donating: “I’M REALLY INTO THIS GUY” and “Stabbed to death with scissors …” are among the political email headers that flooded into a Grid test mailbox recently.

Don’t expect it to change any time soon.

Experts say a combination of factors is driving this email arms race. Baby Boomers, the most generous pool of political donors, are particularly willing to hand over cash in response to email come-ons. And Facebook and Twitter’s strict limits on political ads have weakened social media’s fundraising power. Meanwhile, the Republican National Committee — which successfully pushed Google to loosen Gmail’s spam filter to allow more political emails through — is now suing the company in federal court seeking further concessions.

At the same time, the total raised per individual email seems to be going down, creating a vicious cycle where campaigns must send more messages to rake in the same amount of cash. With a few exceptions, an email that would raise $25,000 a few campaign cycles ago now brings in just a few thousand dollars, a senior adviser to several national-level Democratic campaigns and organizations told Grid. This means campaigns need to send more messages just to hit the same goals.

Jared Leopold, who has worked on dozens of Democratic campaigns at all levels, said that former president Barack Obama’s record-setting 2008 fundraising campaign — which raised more than $1 billion while relying heavily on email come-ons — created a whole new world of fundraising online “that is oftentimes the wild, wild West.” Several other experts echoed that sentiment in interviews with Grid.

“You have legitimate candidates pushing urgency, you have legitimate candidates pushing bizarre match deals, and then you also have a bunch of scam artists out there who give maybe 5 cents on the dollar to the actual candidates and take the rest for themselves,” said Leopold, now the co-founder of climate advocacy group Evergreen Action. “It is a real uncharted territory, and everyone’s in it because it’s a cash cow.”

The dark art of email subject lines

Campaigns rely on a mix of fundraising tools — from social media to dinners for big donors — but email has proved a particularly intimate, and profitable, avenue. “It’s great for driving traffic, driving attention, reader engagement, it’s amazing for monetization,” said Dan Oshinsky, who runs the email consultancy Inbox Collective.

As part of reporting this story, Grid set up a fresh email account on Oct. 5 and subscribed only to updates from the two main candidates running for the Senate from Pennsylvania — Democrat John Fetterman and Republican Mehmet Oz.

The account received more than 90 campaign emails over the next 28 days. The subject lines included a Fetterman message from “John’s iPhone” with the subject line “hope I make u proud [<3]” and an Oz email with the header “Like a slap in the face — he is relentless.”

Grid also asked several people who regularly receive large numbers of political fundraising emails to share the worst and most misleading subject lines they’d seen. Among them: Emails referencing “Your at-home COVID-19 test” or a past-due bill, even though their purpose was to solicit political donations. These misleading subject lines can boost email open rates — getting campaigns past the first hurdle, making sure someone sees their message.

Businesses can’t use these kinds of grabby but misleading email subject lines, which are prohibited by the federal CAN-SPAM Act. But political campaigns and partisan groups fall into a legal gray area. Email strategies that would in theory subject a company to regulatory scrutiny, or perhaps fines or penalties, are permissible when employed by a campaign or political group because their emails are not considered commercial under the federal spam law.

“You certainly see senders on the political side abuse that freedom to send, taking actions and things that I personally wouldn’t recommend to folks,” said Oshinsky.

That behavior isn’t limited to one party. But Jake Sticka, vice president of client strategy at the digital marketing agency Rising Tide Interactive, said that he sees greater use of these tactics on the Republican side and quickly ticked off several examples.

One email from Donald Trump’s Save America PAC asked voters to split a donation between him and Republican Blake Masters, who’s running for the Senate in Arizona. Clicking through to the actual donation page reveals that roughly 99 percent of any donations would go to Trump’s group, with 1 percent going to Masters.

Then there’s J.D. Vance, the Republican candidate for Senate in Ohio, whose campaign has been sending emails telling people that they can get a 15-times match on their donations, meaning that if someone donates $1, other donors will donate up to $15 to match it.

“That’s pretty difficult to do as a Senate committee within [federal election] law,” said Sticka. “I would be very surprised if a 15-times match is true.”

His third example came from Sen. Ron Johnson, Republican of Wisconsin, who’s running for reelection. Johnson’s campaign sent an email that said he hadn’t received any donations yet that day and the recipient could become his first grassroots donor of the day by giving money, Sticka recounted.

Representatives for Trump, Masters, Vance and Johnson have not yet responded to Grid’s requests for comment.

“I just see lots of these pretty verifiable lies going out on the Republican side that I don’t on the Democratic side,” said Sticka. “There are times where the language is tactical, but I find the Republican side is using far more misleading tactics on the whole.”

Other sources Grid spoke to echoed these concerns.

Wheeling and dealing subscriber lists

Signing up for one candidate’s emails can also result in an email address being shared with other candidates and companies in ways users don’t expect. There is an array of digital-strategy firms on both the Democratic and Republican sides that work with campaigns, and some sell email lists to other entities or use them for other clients.

That’s driven in part by Google, Twitter and Facebook’s decisions to tamp down on political ads on their platforms. Campaigns from both parties pivoted to the old-fashioned strategy of buying, selling and trading email lists. Many even spun up whole subsidiaries dedicated to list-brokering.

But that can involve selling the email addresses of people who either didn’t consent to have their information sold or shared or didn’t realize that such consent was buried in the fine print when they signed up for a candidate’s list. “I have heard of [campaign-consulting] firms who have in their contracts [that] in the event that you lose your race, the firm has the ability to share the emails that you’ve acquired with their other clients,” said Sticka.

Both Republicans and Democrats do this, but Leopold, a Democrat, said that Republicans have pushed even further into the realm of total monetization. “There is a nexus between Republicans’ email lists and health supplements and doomsday prep, that kind of for-profit stuff,” he said. “And part of the reason I think that Republicans even had more trouble with getting their emails through on Gmail is because they’ve fully bought into this kind of profitization of political email lists.”

Take the 99-1 donation split Sticka mentioned between Trump and Masters. While Trump gets most of the money raised under the arrangement, Masters gets access to information about members of Trump’s mailing list — who he can then hit up later for more money.

Grid’s inbox, signed up for Fetterman’s and Oz’s emails, received messages soliciting donations for candidates such as Val Demings, a Democrat running for the Senate in Florida, and Adam Laxalt, a Republican running for the Senate in Nevada — sent from generic Fetterman and Oz email accounts, respectively.

But experts told Grid that list-sharing often begins in earnest after a candidate loses, rather than during a campaign cycle.

Outwitting spam filters

While there are specific laws governing commercial emails, which aim to get you to purchase something or engage in a commercial transaction, political speech is protected by the First Amendment. And federal laws on spam are aimed at commercial email, rather than the bucket that political emails fall into: noncommercial.

But some political emails do qualify as spam by common definitions, if not government regulations.

“The definition of spam is unsolicited emails,” said Yanna-Torry Aspraki, an email and deliverability specialist at EmailConsul, a deliverability monitoring tool. “I might have given you my email. I’m might even have given you consent to send me emails — but I’ve given you consent to send me one email a week or whatever I was expecting, not sending me 30,000 emails a day or emails that I’m not expecting. That’s considered spam, even if I’ve given you consent.”

That can sometimes backfire, with greater volumes or unexpected senders making it more likely that messages will get caught in spam filters.

In general, Oshinsky said, email spam filters are looking at how recipients engage with emails to help determine what is spam. “They’re looking at positive signals like when someone opens, someone clicks, replies to an email, stars an email or moves it to a folder — basically anything that says like, ‘Oh, this email was valuable because someone took an action as a direct result of this email being sent and showing up in their inbox,’” he explained.

Conversely, negative signs such as someone ignoring an email, deleting it or moving it to the spam folder signal to the filter that a message is unwanted. Volume is also a factor. If a spam filter detects a massive increase in the number of emails being sent by a single sender, or a large increase in the number of people on a particular mailing list, it’s more likely to consider those messages spam. That can be tricky for campaigns, which often dramatically increase the number of emails they send out in the final days and weeks before an election, and trade lists to increase their reach.

To address such issues, many email providers use sophisticated tools to help reputable groups with large email lists make sure their messages reach the intended recipients.

But that doesn’t necessarily satisfy large list-owners — like the RNC, which sued Google last month over its pilot program to help political emails bypass its spam filter. The RNC, which has not signed up for the service, is basing its case in part on a recent study that found Gmail sent Republican emails to spam more often than other emails. (The study’s authors say their findings have been misconstrued by Republicans and that there is no evidence that Gmail was purposely targeting Republican emails.)

In the meantime, the reality is that email fundraising works, and its pace and tone are unlikely to change any time soon.

“My personal view was that a lot of these senders have been in the spam folder because they have not been following the best practices, because they’re using shady subject lines, or they’re buying email lists, or they’re not setting up authentication,” said Oshinsky. “If that’s the case, that doesn’t really have anything to do with Gmail, or Yahoo, or Outlook, or any of these other email inboxes banishing messages to the spam folder. That’s a direct result of the senders themselves not following the best practices that the rest of us are.”

Thanks to Lillian Barkley for copy editing this article.