A senior official at the Children and Youth Investment Trust Corp. raised concerns as early as 2008 that a nonprofit organization linked to former council member Harry Thomas Jr. was using the agency as a “check-on-demand place” but was overruled within the agency, according to e-mails obtained by the D.C. Council.

At a D.C. Council hearing Monday to evaluate the trust’s performance, Council member Jim Graham (D-Ward 1) offered a glimpse into his investigation into the agency’s relationship with Langston 21st Century Foundation, which allegedly funneled payments to Thomas. Last month, Thomas pleaded guilty to using more than $350,000 in city money that came through the trust and Langston for his personal use.

Graham, the chairman of the Human Services Committee, spent more than two hours grilling Ellen London, the chief executive officer of the trust, about how the public-private agency justified its payments to Langston in 2008. Documents obtained by the council show repeated six-figure payments were forwarded to Langston even though some officials worried there was not enough justification for how the money was being spent.

In an e-mail exchange in February 2008, the trust’s vice president of finance appeared to push back against a request for a $96,000 disbursement to Langston a week sooner than he had planned, according to e-mails Graham read into the council record. At the time, trust staffers were becoming worried that Langston had failed to enter grant performance data into an online tracking system, as required.

“Of course, we can make a special exemption,” wrote Timothy Fitzsimmons, who has since left the agency. “I would rather not, as we have to start managing people’s expectations that we’re a check-on-demand place.”

London, who was also a vice president at the time, responded, “Politically sensitive. As I thought, M. would like this check earlier . . . Any options?”

Graham declined to publicly release the e-mails Tuesday. But a person with access to them allowed The Washington Post to review the documents. Additional e-mails obtained by the council suggest London was referring to Millicent D. West, who then was director of the trust.

West, who later became the District’s homeland security director but resigned last month, did not testify at the hearing. In a brief interview Monday night, she denied that the Langston foundation received special treatment.

“There are a number of organizations that from time to time would have some deviation from the normal operating procedure,” West said, declining further comment.

London, who became director of the trust in June 2010, testified that she did not recall any instances where direct “political pressure” concerning spending decisions was placed on her or West. But under questioning from Graham, London acknowledged that the agency treated spending requests that came from a council earmark differently because they were designated for a specific purpose.

“Earmarks came to us as a done deal,” London said. “I think people were trying to figure out how to handle them.”

Prosecutors allege that Thomas arranged for the trust to grant city funds to Langston Golf Course in Ward 5. A foundation set up by the course then sent $306,000 back to two groups allegedly controlled by Thomas, prosecutors say.

Two Langston officials, Marshall D. Banks and James Garvin, have been charged with not reporting Thomas’s theft.

Graham, who put London and eight of her associates under oath, detailed how some decisions were made within the trust in 2008.

Neil Rodgers, Thomas’s top council staffer, submitted a request on behalf of the Langston foundation on Jan. 15, 2008, e-mails show. According to Graham, the trust’s chief financial officer questioned the thoroughness of the submission, but the application was approved within days.

“The council members wants to know [which] day this week they can send someone to pick up the check,” Rodgers wrote in an e-mail to the agency, Graham said.

On Jan. 25, 2008, the trust issued a $100,000 check to Langston. London testified that it was customary for grantees to receive an “advance” of up to 25 percent before any work was done.

E-mails reviewed by The Post also show Rodgers wrote to London in February 2008 asking, “When can Jimmy Garvin pick up the check.”

By late September, e-mails show, trust officials were becoming concerned that the Langston foundation was not submitting proper documentation for its work, including entering data into Webstar, an online tracking tool. But payments to the non-profit organization continued.

“I talked to Millicent and she is o.k. in proceeding without the data being entered into Webstar,” Jacquelyn Lendsey, a vice president at the trust, wrote to Fitzsimmons on Oct. 1, 2008, according to e-mails reviewed by The Post.

London noted that 22 grantees, including Langston, were behind on their compliance requirements.