A little-known private foundation controlled by Bill and Hillary Clinton donated $100,000 to the New York Times’ charitable fund in 2008, the same year the newspaper’s editorial page endorsed Clinton in the Democratic presidential primary, according to tax documents reviewed by the Washington Free Beacon.

The Clinton Family Foundation, a separate entity from the Bill, Hillary and Chelsea Clinton Foundation, has been the family’s vehicle for personal charitable giving since 2001.

It is funded directly by the Clintons and distributes more than $1 million a year to civic and educational causes.

The New York Times Neediest Cases Fund is a charity affiliated with the newspaper that assists underprivileged New Yorkers. It is run by members of the New York Times Company’s board of directors and senior executives.

The Times’ editorial board endorsed Clinton against Democratic challengers John Edwards and Barack Obama on January 25, 2008, writing that she was "more qualified, right now, to be president."

At the time, there were reports that the Times board had leaned toward endorsing Obama, but was overruled by then-chairman and publisher Arthur Sulzberger Jr., whose family controlled the paper. Sulzberger’s cousins and Times Company directors, Lynn Dolnick and Michael Golden, chaired the New York Times Neediest Cases Fund in 2008.

The Clinton Family Foundation did not list the specific date the donation was made in its public tax disclosure forms. Neither the Times nor a representative of the Clintons responded by press time to a request for comment. Clinton ended her presidential campaign on June 7, 2008.

The CFF’s $100,000 contribution to the New York Times Neediest Cases Fund is larger than its typical donations.

Of the 47 organizations the CFF donated to in 2008, only six groups received more than $50,000. Most received between $2,000 and $25,000. The CFF has not donated to the Neediest Cases Fund since 2008.

The Times endorsement was controversial at the time because there was speculation about whether it was swayed by pressure from the Clintons.

In February 2008, the New Republic reported that the Times editorial board had had two contentious meetings that January before Sulzberger "tipped the scales in [Clinton’s] favor."

Vanity Fair also reported that May that Sulzberger intervened in favor of Clinton after he was lobbied heavily by one of Clinton’s top financial backers.

"The Times editorial board was, apparently, planning to endorse Barack Obama in the New York primary; the Clinton campaign, getting wind of this, called upon one of its major financial supporters [Steven Rattner], the best friend and principal adviser of Arthur Sulzberger Jr.," Michael Wolff wrote in Vanity Fair.

"Rattner is thought to have petitioned Sulzberger, and Sulzberger thereupon overruled his editorial board, which then backed Clinton."

Andrew Rosenthal, the New York Times editorial page editor, denied the Vanity Fair story at the time, calling it "completely false."

The CFF’s largest contribution in 2008 was $1,000,000 to the Bill, Hillary and Chelsea Clinton Foundation (then named the William J. Clinton Foundation). The donation made up nearly half of the $2.4 million the foundation dispersed that year.

The CFF’s donations to the Bill, Hillary, and Chelsea Clinton Foundation continued to dwarf its other distributions between 2009 and 2013. The Clintons gave their higher-profile foundation $352,000 in 2011, $220,000 in 2012 and $300,000 in 2013.

Hillary Clinton served as the CFF’s treasurer during her tenure at the U.S. Department of State and listed it in her financial disclosures. The Washington Post reported in 2007 that Clinton had previously omitted her role at the foundation in her Senate disclosure forms.

The Clintons also contributed $35,000 to the Diane Blair archive at the University of Arkansas Special Collections between 2006 and 2011. The Free Beacon was briefly banned from the library last summer after reporting on documents from the Blair collection and others that shed light on Clinton’s legal defense of a child rapist.

The Blair papers were closed to the public during Clinton’s last presidential campaign. They were opened for the first time in 2010.

The CFF also contributed to the Dale Bumpers archive housed in the same library. The University of Arkansas Special Collections pulled Bumpers’ diary from the archive in March at the request of his family after Mother Jones reported on unflattering entries about the Clintons.

In addition, the CFF gave $207,000 between 2006 and 2013 to the Central Arkansas Library System, a public library which houses Bill Clinton’s papers from his time as Arkansas governor. Access to the collection is tightly restricted, and must be approved by the Bill, Hillary, and Chelsea Clinton Foundation.