A mysterious group behind a celebrity ad campaign aimed at convincing GOP electors to cast their electoral votes against Donald Trump on Monday is led by a liberal political operative who in the past has deployed questionable — if not creepy — tactics.

Americans Take Action is listed as the backer of the ads, which were published online last week and feature Martin Sheen, Debra Messing and other actors pleading with Republican electors to dump Trump.

There is little public information about the group. It is listed as a 501(c)(4) group and is registered in Maryland. But a deeper investigation by The Daily Caller reveals that a liberal activist named Ryan Clayton is heavily involved in its operations.

Clayton, who has written for The Huffington Post and founded the left-wing site, US Uncut, served as campaign chairman for Lawrence Lessig, the Harvard professor who ran for president last year on a platform of reforming the electoral and campaign finance systems. (RELATED: Hollywood Celebs Misgender Kansas Elector That They Hope Will Dump Trump)

In an interview with an Oregon news outlet published this weekend, Clayton urged electors to reject Trump because of questions about the Republican’s relationship with Russian president Vladimir Putin.

“If Putin picked our President, not We the People, then Trump must be rejected by the Electoral College,” Clayton told KTVZ.

“Trump is a clear and present danger to our country and the world. The men and women who died for our freedoms deserve better than this,” he added.

[dcquiz] Lessig, Clayton’s mentor, is involved in a group called The Electors Trust, which also aims to convince some of Trump’s 306 electors to choose another person — anybody but Trump, they say — for president on Monday. Lessig told TheDC that he is not involved with Americans Take Action or the celebrity ad campaign.

But his protege, Clayton, was linked to questionable activities during two separate Democratic primaries earlier this year.

The operative appears to have paid for the printing and distribution of handwritten letters sent to women in Portland, Maine just before a Democratic state senate primary in June smearing a candidate he opposed.

He was also connected to deceptive pamphlets sent out to voters before a Democratic primary contest in Portland, Ore. The candidate Clayton was trying to help publicly asked the group behind the mailers to “put a tag line on” the pamphlets “and follow the law.”

The common thread between the new celebrity ads and the shady mailings is Clayton’s laser-like focus on campaign finance and electoral reform.

Americans Take Action is one of numerous progressive groups that are begging electors to vote against Trump on Monday. The groups, which plan protests at state capitols across the U.S., hope to convince at least 37 electors who live in states that Trump carried on Election Day to cast their votes for anyone but the Republican.

If the long-shot effort somehow succeeds, the House of Representatives will select the next president. Trump would likely prevail in that scenario, but Democrats would be expected to use the mass exodus to try to de-legitimize his presidency.

Americans Take Action, which is affiliated with another amorphous group called Unite for Change, has created several versions of the celebrity ads. Some are addressed to all GOP electors. But the group has also made ads that are personalized for individual Republicans.

On Saturday, an ad surfaced that was aimed at Kansas GOP elector Ashley McMillan Hutchinson. In the ad, Sheen and actor Bob Odenkirk address Hutchinson by name. But Sheen calls her “Mr. Ashley McMillan” in the ad and leaves off her married name.

Hutchinson told TheDC on Saturday that the groups behind the spot have not sent the ad to her. She also said that a Facebook friend of hers in Kansas notified her that he saw the spot in his news feed.

The group’s ads began airing on TV over the weekend, USA Today reported late Saturday. The newspaper did not identify Americans Take Action, instead reporting that a coalition of progressive groups is spending $500,000 to air the non-personalized ads across the U.S.

The fact that the ad personalized for Hutchinson appears to have been made public rather than sent directly to her raises questions of whether it is intended more as an intimidation tactic than a personal plea for Hutchinson to change her mind.

It also comes amid reports that electors are receiving hundreds of emails attempting to sway their vote on Monday. Some have even received death threats.

Asked about Americans Take Action’s tactics, Hutchinson, the Kansas elector, said she does not believe the group will be successful.

“I think political operatives try to win at all costs. I respect that work ethic. I do believe their efforts will be fruitless,” she told TheDC.

But the ad campaign wouldn’t be the first time that a Clayton-linked project has used questionable tactics to sway voters.

In June, Maine newspapers reported that Clayton paid for handwritten letters that were sent to female voters in the Portland area that were critical of Benjamin Chipman, a Maine state representative who was running for an open senate seat.

The letters alleged — falsely, apparently — that Chipman was a “slumlord” and had had several restraining orders filed against him.

Clayton appears to have wanted Chipman’s challenger, Diane Russell, to win the election because of her advocacy for electoral reform. Russell supported getting rid of the superdelegate system that Democrats use to pick primary winners.

Chipman, who ended up winning the primary and the general election, told a Maine newspaper that he received messages from approximately 50 women who received the letters. He said the effort was “designed to instill fear” in his supporters.

“Somehow they got some data from somewhere about women who were supporting me,” he told the Portland Press Herald.

Clayton, who gained national attention in 2012 after he had a heated exchange with Andrew Breitbart, the conservative activist and publisher, was also identified as the operative behind deceptive mailers sent out in a Democratic primary contest in Oregon earlier this year.

Americans Take Action sent propagandized voter’s guides ahead of a primary race between Sharon Nasset and Tina Kotek, the Democratic incumbent and speaker of the Oregon House.

The mailers made false allegations about Kotek’s resume and her business associations. Nasset claimed at the time that she did not know about the mailers, and she publicly asked that whoever was responsible to back off.

Americans Take Action reported contributions of $1,822 and $4,590 to Nasset’s campaign in May for the printing and distrubiton of brochures and campaign literature, and Clayton donated $200 to the campaign.

As the Willamette Week reported in May, Americans Take Action appeared to have coordinated with Wolf PAC, a political action committee that Clayton directs.

Wolf PAC was founded by Cenk Uygur, the former MSNBC host and anchor of The Young Turks, a political show that airs online. Clayton is currently paid around $3,900 a month as executive director of Wolf PAC, according to disclosures filed with the Federal Election Commission.

According to the Willamette Week, Wolf PAC hammered Kotek in February over her refusal to support a resolution that would have called on the U.S. Congress to amend the Constitution by overturning the Supreme Court’s Citizens United decision.

Questions were also raised during that election about Nasset’s disclosure of Americans Take Action’s in-kind contributions to her campaign.

Nasset, who ended up losing to Kotek, failed to disclose the contributions as quickly as she should have.

TheDC was not able to determine whether Americans Take Action is spending to push the celebrity ads through Facebook or how many other personalized ads may have been produced. The group is not registered with the Federal Election Commission. It likely would not be required to disclose its expenses anyway given that its expenses are not being used in a popular election scenario.

Reached by TheDC by phone on Sunday, Clayton said he was unable to talk. He said he would call back but never did.

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