Donald Trump’s charitable foundation gave $100,000 in 2014 to a conservative activist group that was used to help finance a federal lawsuit against New York state Attorney General Eric Schneiderman — the same public official who was suing the real estate mogul for fraud over the operations of Trump University.

The size and timing of the donation to the Citizens United Foundation, an arm of the sprawling conservative network run by David Bossie, who is now Trump’s deputy campaign manager, could raise fresh questions about whether Trump has used his tax-exempt charity to further political and personal causes.

It is a claim, actively promoted by Hillary Clinton’s campaign, that got new attention this week after Trump’s foundation acknowledged paying a penalty to the IRS for an improper $25,000 donation to Florida Attorney General Pam Bondi’s reelection campaign during a time her office was considering whether to join Schneiderman’s lawsuit against Trump University.

A review of tax returns filed by the Trump Foundation shows that the 2014 donation to Bossie’s Citizens United Foundation was by far the largest it gave to any organization that year, substantially exceeding its contributions to more traditional charities, such as the Leukemia and Lymphoma Society (which got $50,000), the Dana-Farber Cancer Institute ($25,000) and the Police Athletic League ($25,000).

It was also the first time the Citizens United Foundation had ever received funding from Trump’s charity.

Donald Trump arrives at a campaign rally in Tampa, Fla., with Florida Attorney General Pam Bondi on Aug. 24, 2016. (Photo: Gerald Herbert/AP)

While the donation to Bossie’s group has been mentioned in some media accounts, what has gone unnoticed until now is a major project of Citizens United at the time: a lawsuit it filed that year — since dismissed by a federal judge — against Schneiderman, New York’s Democratic attorney general, over his efforts to require nonprofit groups such as Citizens United to disclose the identity of their donors under seal to the New York State Charities Bureau.

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Schneiderman by then had become a major political nemesis of Trump. In 2013, Schneiderman had filed his own lawsuit, still pending in New York state courts, accusing Trump of ripping off students at Trump University through fraudulent and deceptive trade practices, promising to teach them to “make a killing” in the real estate market but, according to the suit, delivering courses that had little if any value.

Trump, in response, launched a public relations and legal counterattack against Schneiderman. He accused him in a Twitter barrage of being a “lightweight hack” who brought the suit for political purposes. He filed a complaint against Schneiderman with the New York ethics agency (since dismissed) over donations the attorney general had solicited from his daughter Ivanka Trump and her husband, Jared Kushner, while his office was investigating Trump University. Trump, in a later interview, described Schneiderman as “a low-life, a sleazebag” who was part of a “cesspool of corruption” in New York politics.

Students enter a Holiday Inn to take the free intro class at Trump University in 2009. (Photo: Sarah L. Voisin/The Washington Post via Getty Images)

The attack on Schneiderman’s tactics was soon reinforced in the lawsuit filed by Citizens United and the Citizens United Foundation on May 24, 2014, by the lawyer for both groups, Donald F. McGahn, a Republican campaign finance attorney and former Federal Election Commission chair who is now the chief counsel for the Trump presidential campaign. (Citizens United is a “social welfare” organization that is permitted to engage in political activity. The legal battle over its film critical of Hillary Clinton led to the controversial 2010 Supreme Court decision permitting corporations, unions and wealthy donors to spend unlimited amounts on political ads. The Citizens United Foundation is an affiliate “educational” charity that is located at the same Washington, D.C., address with the same phone number. Both groups are headed by Bossie.)

Bossie charged — in a press release still displayed on the Citizens United Foundation website — that he brought the suit because the “First Amendment was under attack by the New York Attorney General.” In court documents, he asserted that major donors had pulled back from donating to his organizations because they feared their identities would become public if Citizens United submitted its list of donors to Schneiderman’s office and this had infringed on Citizens United’s constitutional right to criticize the New York attorney general. As an example, Bossie submitted a draft fundraising appeal that he said he was unable to send out, due to the fears expressed by his donors, that accused Schneiderman of being an “out of control tyrant.” (Another draft fundraising appeal submitted by Bossie in the lawsuit solicited funds for another film that would expose “the real, ruthless Hillary Clinton” and how she left “four Americans to die in Benghazi.”)

The Trump Foundation’s tax return for 2014 lists the purpose of its $100,000 donation as “general” support for the activities of the Citizens United Foundation. The Citizens United Foundation’s tax return for that year lists as, among its three major activities, its “legal research and judicial action program” that included “litigation support in defense of human and civil rights.”

A spokesman for Schneiderman said that neither the attorney general nor other senior officials in his office were aware that Trump’s charitable arm had given money to the Citizens United Foundation until it was brought to their attention this week by Yahoo News.

New York Attorney General Eric Schneiderman speaks at a news conference in New York in March. (Photo: Seth Wenig/AP)

But after being provided a copy of the Trump Foundation’s publicly filed tax return, showing the donation was made the same year that the Citizens United Foundation filed its lawsuit against Schneiderman, the spokesman, Eric Soufer, said in an email: “If Donald Trump has proven anything over the past three years, it’s that he’ll do anything to pursue his bizarre but predictable vendetta against this office. … Funding a meritless lawsuit against this office would be nothing new for someone like Donald Trump, who has filed baseless ethics complaints, planted bogus stories, and tweeted a steady stream of incoherent insults just to make himself feel better for being exposed as the fraud he clearly is.”

Trump’s campaign did not respond to requests for comment. But in an email, Michael Boos, Citizens United’s executive vice president and general counsel, said “there is no relationship at all between the gift [from the Trump Foundation] and our lawsuit challenging the New York Charities Bureau’s demand for donor lists from nonprofit organizations soliciting contributions in New York. The timing of the lawsuit was based on Schneiderman’s efforts at the time to gain access to the donor information.

Bossie did not initially respond to requests for comment for this story. But after it was published, he sent Yahoo News this email on Friday: “Eric Schneiderman’s Nixonian tactics of intimidation are the exact reason I filed suit against him in May, 2014. My mission as President of Citizens United was to defend the First Amendment rights of American citizens, something Mr. Schneiderman has actively worked against his entire career. Furthermore, as recently as this week, details have come to light that have exposed Mr. Schneiderman as the man who excused Hillary Clinton from disclosing foreign donations to the Clinton Foundation. Mr. Schneiderman is a hypocrite, and it is blatantly obvious he believes his singular responsibility is to advocate for a special set of rules for the Clinton family – something he’s been successful at when he isn’t busy abusing the First Amendment rights of everyday Americans.”

Late last month, U.S. Judge Sidney H. Stein in New York dismissed the Citizens United lawsuit, concluding that its complaint “states not a single plausible claim upon which relief can be granted.” Boos of Citizen United said the organization is now considering whether to appeal.