A GOP dirty tricks operation, exposed

Following the breadcrumbs from a “progressive” super PAC to a powerful Republican operative

On April 24, a new super PAC called Lead Left quietly filed a Statement of Organization with the Federal Election Commission (FEC). According to the group’s website, “Lead Left PAC stands against MAGA extremists who will infect our country with Donald Trump’s agenda.”

On May 7, Lead Left began spending heavily in Democratic primaries. Since that time, the group has spent over $3 million in support of Democratic House candidates in key races across the country.

But, as Punchbowl News and others have noted, Lead Left’s spending patterns are unusual. It is backing Democratic candidates in competitive districts with major political liabilities. For example, in Texas, Lead Left has spent over $900,000 supporting Maureen Galindo in the Democratic primary. Galindo, a sex therapist, has made a series of antisemitic comments. In an Instagram post, Galindo pledged to transform ICE detention centers into a “prison for American Zionists” and a “castration processing center for pedophiles which will probably be most of the Zionists.” Galindo’s campaign has raised less than $11,000, of which $4,100 was a contribution from the candidate.

Galindo is running in Texas’ 35th District, a seat that was redistricted to favor Republicans. The DCCC has endorsed Galindo’s primary opponent, Johnny Garcia. Lead Left has also intervened in Democratic primaries in swing House districts in Nebraska and Pennsylvania.

Lead Left has gone to great lengths to conceal its identity and backers. It listed its address as a mailbox at a Staples on 2241 North Monroe Street in Tallahassee, Florida. Its treasurer, Tammie Cannon, has no political connections or online footprint. It was also created to maximize the amount of time it could operate without disclosing its donors. Although it has already spent millions, Lead Left will not have to disclose the source of its funds until June 20, after most primaries are over. The money is being funneled to two shell companies that have been formed in the last few weeks.

A Popular Information investigation, however, found that Lead Left is linked to Caleb Crosby, a Republican operative. Crosby is the treasurer of the Congressional Leadership Fund (CLF), the primary super PAC of the House Republicans. CLF raised over $250 million last cycle. Crosby is also the treasurer of the Senate Leadership Fund, the super PAC for Senate Republicans.

Several pieces of evidence point to Crosby’s involvement. First, of the roughly 48,500 distinct political committees that have filed with the FEC since 2016, only two others share an address with Lead Left — the Staples at 2241 North Monroe Street in Tallahassee. Both of those committees are connected to the Crosby Ottenhoff Group, the political compliance firm founded by Crosby.

One of the groups located at 2241 North Monroe Street was Fight Right Inc, the super PAC that spent over $14 million supporting Florida Governor Ron DeSantis in the 2024 Republican presidential primary. The Treasurer for Fight Right Inc was Kaylen Melton, a CPA at Crosby Ottenhoff. Melton lists her Crosby Ottenhoff email as the primary contact for Fight Right Inc.

The other group listed at 2241 North Monroe Street is Justice Truth, a super PAC that was also active during the 2024 cycle. The treasurer of the group is another GOP operative linked to Crosby Ottenhoff, Thomas Datwyler.

Justice Truth only raised a few thousand dollars but Datwyler gained more notoriety in 2024 for his connection to a super PAC called Roosevelt Society Action. Roosevelt Society Action appeared abruptly and spent hundreds of thousands of dollars attacking Democratic Senator Sheldon Whitehouse (RI). Datwyler’s home address was listed as the address for the Roosevelt Society, which donated $200,000 to the group. (Datwyler refused to reveal the actual source of the funds.) Like Lead Left, Roosevelt Society Action tried to portray itself as left-leaning. Its ads promoted the website of the Roosevelt Institute, an actual progressive organization.

The treasurer of Roosevelt Society Action? Kayla Glaze, a CPA for Crosby Ottenhoff.

There are more clues linking Lead Left to Crosby Ottenhoff and Caleb Crosby. As noted by Nebraska Public Media, the original Lead Left website contained the following snippet of code:

WinRed is a Republican fundraising website. Standing Tall Action is a 501(c)4 non-profit organization. In a 2024 filing with the IRS, the most recent available, Standing Tall Action lists Zac Funderburk as its Treasurer. Funderburk is an employee of Crosby Ottenhoff.

There are also substantive similarities between the messages pushed by Lead Left and those by organizations that are formally linked to CLF.

In Nebraska, the American Action Network, the affiliated non-profit of the CLF, sent mail and ran digital ads seeking to damage House Democratic candidate and John Cavanaugh by linking him to Trump. The digital ads said Cavanaugh was “working to enact Trump’s policy here in Nebraska,” noting that they both had proposed eliminating taxation on tips and overtime. The mailers showed Cavanaugh side-by-side with Trump with the banner “SAME TAX PLAN. SAME AGENDA. MAKING NEBRASKA GREAT AGAIN.”

Before the Democratic primary, Lead Left then ran television advertisements with a nearly identical message. It claimed that Cavanaugh wanted to “exactly mirror” Trump and was “in agreement” with Trump’s policies. “Keep MAGA John Cavanaugh out of Congress. Lead Left PAC is responsible for the content of this ad,” the spot concludes.

On May 12, Cavanaugh lost to his Democratic primary opponent, Denise Powell, by about 1,100 votes.

Crosby and CLF did not respond to a request for comment.