Donald Trump’s charitable foundation gave a whopping $100,000 to a conservative group pursuing legal action against the New York attorney general at the same time that office was conducting a fraud probe into Trump University, Yahoo News reported Friday.

The Donald J. Trump Foundation’s sizable 2014 gift to the Citizens United Foundation marked the first time it had ever donated to the group, and was “by far the largest” gift the foundation gave to any organization that year, according to the report.

It happened to come as the Citizens United foundation, which is part of a GOP activist network run by Trump’s newly-hired deputy campaign manager, David Bossie, was pursuing a lawsuit against Attorney General Eric Schneiderman for his efforts to require nonprofit groups to disclose the identity of their donors. That suit has since been dismissed.

Schneiderman was the only attorney general to pursue allegations that Trump’s seminar program used misleading marketing materials to encourage students to sign up for costly real estate courses that were essentially worthless. The suit is still pending in state court in New York.

Florida Attorney General Pam Bondi’s office announced in 2013 that it might join Schneiderman’s probe, but ultimately decided against it. A political committee backing Bondi’s re-election campaign received $25,000 from Trump’s charity just days before her office said it wouldn’t take up the case.

Hillary Clinton’s campaign has accused Trump of engaging in “pay-to-play” for donating to Bondi while her office was deciding whether to pursue a case against the real estate mogul.

According to Yahoo, the revelation about Trump’s donation to the Citizens United Foundation “could raise fresh questions about whether Trump has used his tax-exempt charity to further political and personal causes.”

Trump’s relationships with both Bondi and Bossie have grown even closer in the years since the Trump University came under scrutiny. Bondi endorsed Trump and has appeared on the campaign trail alongside him. Just last week, the real estate mogul announced that Bossie would join his campaign.

Trump’s campaign and Bossie did not respond to Yahoo’s requests for comment on the Citizens United donation, although the group’s executive vice president and general counsel, Michael Boos ,told the news site there was “no relationship” between the gift and the lawsuit against Schneiderman.

Schneiderman’s office said they were not aware of Trump’s donation at the time, but after Yahoo showed his staff a tax return that included the donation, spokesman Eric Soufer told Yahoo in an email that it was characteristic of Trump’s “vendetta against this office.”