Political nonprofits like the Sixteen Thirty Fund often experience drops in activity in odd-numbered years, between national elections, before picking up fundraising during midterm or presidential election years. Sixteen Thirty Fund won’t have to file tax returns detailing its total activity this year until late 2021, but its high-flying 2019 fundraising may foreshadow huge 2020 spending from the group.

“It shows how much they grew under the Trump administration,” said Anna Massoglia, investigative researcher at the Center for Responsive Politics. “It’ll be interesting to see what they do under a Biden administration, because they have really thrived in this resistance-centered role. They really have ushered in a new era of more sophisticated dark money.”

Already, public disclosures show that Sixteen Thirty Fund contributed more than $40 million to Democratic-aligned super PACs and other federal groups in 2020, a ten-fold increase over its super PAC contributions in 2018, as well as additional millions to state-level political groups and ballot measure organizations.

“In 2019 and 2020 many donors felt compelled to give as never before to support our democracy and advance progressive goals, including some who previously supported Republicans or were not engaged in politics,” Sixteen Thirty Fund Executive Director Amy Kurtz said in a statement.

More than half of the Sixteen Thirty Fund’s money came from just three anonymous sources in 2019: One donor gave more than $33 million, while another chipped in $29.3 million and a third made a $12.1 million contribution. An additional four contributors gave between $5 million and $10 million in 2019, and 11 more gave at least $1 million. Altogether, those 18 donors gave more than $127 million — more than 90 percent of the Sixteen Thirty Fund’s total inflow last year.

In her statement, Kurtz said Sixteen Thirty Fund supported new laws that would mandate disclosure of donors to groups involved in politics, but it intends to continue raising and spending money without donor disclosure in the meantime.

“We have lobbied in favor of reform to the current campaign finance system (through H.R. 1), but we remain equally committed to following the current laws to level the playing field for progressives in this election and in the future,” Kurtz said.

Sixteen Thirty Fund made $65 million in grants to more than 100 different liberal organizations in 2019, according to its tax return. More than one-quarter of that money ($16.5 million) went to ostensibly local nonprofit groups that sprung up last year and spent big money attacking Republican senators up for reelection in key battleground states in 2020.

Sixteen Thirty Fund gave about $4 million apiece to Maine Momentum, Rocky Mountain Values and Advancing AZ in 2019, as well as $2.9 million to Iowa Forward and $1.75 million to Piedmont Rising — groups that spent millions attacking Sens. Susan Collins (R-Maine), Cory Gardner (R-Colo.), Martha McSally (R-Ariz.), Joni Ernst (R-Iowa) and Thom Tillis (R-N.C.) in 2019 as they prepared for the 2020 elections. In Arizona, Colorado and Iowa, the Sixteen Thirty Fund-funded nonprofits were the biggest advertisers in those Senate races in 2019, according to AdImpact, an ad-tracking firm.

The five groups spent a total of $17.3 million on TV, radio, Google and Facebook advertising in 2019 and 2020, according to AdImpact and digital ad databases, suggesting Sixteen Thirty Fund was the central source of most of the groups’ funding, despite their local names and footprints. The ads largely accused the GOP senators of taking money from special interests and hammered their voting records on health care and taxes.

Gardner and McSally lost races this November, while Collins, Ernst and Tillis won reelection.

Early advertising sprees against vulnerable senators were once a hallmark of another “dark money” network: the conservative Koch network, which spent millions attacking endangered Democratic senators in 2013 and early 2014 before Democrats lost the Senate majority in the 2014 elections.

Other grants from Sixteen Thirty Fund in 2019 included more than $10 million to arms of the League of Conservation Voters and millions more to other environmental groups. A million dollars went to the Movement Cooperative, which helps groups on the left share data and promotes “deep canvassing” efforts. And Sixteen Thirty Fund sent over $7 million to America Votes, which describes itself as “the coordination hub of the progressive community.”

“We saw the impact of these investments in historic vote-by-mail, early vote, and voter turnout numbers in 2020 and look forward to ongoing efforts to keep participation rates high,” said Sahil Mehrotra, national press secretary for America Votes, in a statement.

Sixteen Thirty Fund also gave a $9.3 million contribution in 2019 to North Fund, another D.C.-based nonprofit that was a big player in state ballot measure campaigns and other projects in 2020, including promoting D.C. statehood. North Fund sent more than $5 million to a campaign to legalize marijuana in Montana in 2020, according to state campaign finance records, and it pumped more than $4 million into efforts to expand Medicaid and change ethics and redistricting laws in Missouri. In Colorado, North Fund gave more than $7 million to ballot measure fights, principally fighting abortion restrictions and backing paid medical and family leave.

In addition to making the grants, Sixteen Thirty Fund spent another $33.7 million directly in 2019, including millions on lobbying, legal services and advertising for “fiscally sponsored” groups — nonprofit organizations that operate as trade names under the umbrella of the Sixteen Thirty Fund, which provides administrative and legal services to the organizations.

Prominent groups set up as arms of Sixteen Thirty Fund include Demand Justice, the courts-focused Democratic group that has opposed Trump's judicial nominees, and Health Care Voter, which pressured Republicans on coronavirus response and other health issues in 2020. Sixteen Thirty Fund has 38 active registered trade names, according to D.C. corporate records, focused on issues including election security, health care, taxes and more.

The practice of fiscal sponsorship allows new groups to spin up very quickly, since Sixteen Thirty Fund can take care of administrative tasks like legal, compliance and accounting work for the groups operating under its aegis.

"It’s a very successful model for doing big things very quickly," Kurtz said. "And it’s been incredibly important in the age of Trump, when there were new challenges and problems people hadn’t thought about or dealt with before, or in the age of coronavirus, where eight months before the election we were faced with this reality of doing the entire thing virtually."

The fiscal sponsorship setup also merges all of the groups’ fundraising and spending together on Sixteen Thirty Fund’s tax forms, so it’s impossible to tell how much any one arm of the organization did financially in 2019. And pooling so many different groups together can offer flexibility to spend more anonymous money directly on politics, Massoglia noted, because of an IRS rule requiring that nonprofits spend no more than half of their funds on political activity.

“Some groups are very political, and some are not,” Massoglia said. “So the ones that are much less political act to water down the overall” share of money getting spent on politics, and “that opens them up to be able to spend more directly on political activity.”