A Clinton Foundation official pushed Hillary Clinton's State Department to approve a request for Bill Clinton to speak at a North Korean industrial complex accused of funding the country's rogue nuclear program.

The invitation was facilitated by Tony Rodham, the brother of the Democratic nominee, who had entered now-defunct business partnerships with the Clinton bundler named as a "go-between" for the speech hosts and the secretary of state.

New emails shed light on a paid speech opportunity in North Korea that was first uncovered last year through a batch of documents provided to Citizens United through a Freedom of Information Act lawsuit.

The latest records to emerge from that case, which were obtained by the Washington Examiner, offer additional insight into the effort to persuade Bill Clinton to deliver remarks in the communist country.

Bill Clinton successfully sought State Department approval for 215 speeches while his wife served as secretary of state, earning $48 million on the speaking circuit during her tenure. His frequent addresses to foreign governments and entities that had interests pending before Hillary Clinton's agency has raised questions about potential conflicts of interest.

In March 2012, the former president received an invitation to speak at the Gaesong Industrial Complex in North Korea, where dozens of South Korean companies took advantage of the lower wages permitted north of the demilitarized zone by shifting parts of their operation there.

According to Human Rights Watch, the labor laws governing work at the Gaesong campus "fall well short of international standards."

Sung Chul Park, chairman of a textile manufacturer that employed North Koreans at the industrial compound, invited Bill Clinton to speak at the dedication ceremony for a church he had built on the property. He extended the request through Billy Kim, a Korean-born evangelical leader.

Kim cited a "mutual friend," Richard Park, as the "go-between" who would coordinate the request with Sung Chul Park and Bill Clinton.

Richard Park has donated heavily to Hillary Clinton's political campaigns dating back to her race for a U.S. Senate seat in New York, according to the Center for Responsive Politics. His $100,000 donation to Bill Clinton's second inaugural in 1996 was scrutinized after Richard Park was rewarded with an invitation to a state dinner with South Korea's president.

More recently, Richard Park's friendship with Tony Rodham earned him a direct line to Hillary Clinton while she served as secretary of state. In January 2013, the Korean businessman sent Rodham an email and asked him to "forward this to your sister," according to records released by the State Department in November.

When Hillary Clinton received the message, in which Richard Park wished her well after a stint in the hospital, she instructed her assistant to respond.

Richard Park and Rodham both worked as managers for a company called Eco-Micro Science Technologies, according to records from Nevada's secretary of state. The Carson City-based firm appears to have dissolved in 2011.

When a Clinton Foundation official reached out to Cheryl Mills, Hillary Clinton's chief of staff, in May 2012 to inquire as to whether the State Department would have "concerns" about Bill Clinton speaking in North Korea, the official specified that the invitation "came via Tony Rodham."

Mills replied bluntly: "Decline it."

But Amitabh Desai, the foundation employee, pushed back, asking Mills to provide "any specific concerns ... beyond just saying it would be concerning for [the U.S. government]" given Rodham's involvement. Desai noted Rodham was slated to meet with Bill Clinton "in a couple of hours."

The former president would have pocketed an unspecified fee for the North Korean speech had he delivered it, the invitation showed. Sung Chul Park, the businessman who wanted Bill Clinton to speak at the dedication of his church, would have "taken care of" the "honorarium" typically offered to high-profile speakers.

Sung Chul Park faced questions over alleged tax evasion in 2015 after Korean authorities accused him of purchasing shares in the textile corporation under family members' names.

His company suffered declines in 2013 after North Korea temporarily suspended operations at the Gaesong complex amid an expansion of sanctions resulting from its nuclear tests.

South Korea pulled its operations from the Gaesong campus in February after North Korea tested a long-range missile in violation of international restrictions on its weapons program.

Seoul reportedly accused the North Koreans of diverting money from work performed at the industrial park to its unsanctioned nuclear program.

As much as 70 percent of the wages paid to workers at Gaesong was reportedly confiscated by Pyongyang and spent on its weapons program and luxuries for the country's handful of rulers.

David Bossie, president of Citizens United, said the details of Bill Clinton's flirtation with the North Korean speech raises fresh questions about the former president's paid engagements.

"This new invitation letter makes clear that Bill Clinton will consider taking money from anyone and waste U.S. government time and resources to figure out the details," Bossie told the Examiner. "The American people have a right to know the full extent of Bill Clinton and Tony Rodham's ties to North Korea."

Bill Clinton's frequent and highly-paid speaking engagements, often funded by groups that had donated to the Clinton Foundation or lobbied the State Department, have posed uncomfortable questions to his wife's presidential campaign.

Hillary Clinton has struggled to address recent revelations that donors to her family's foundation were afforded special access above what was given to other agency outsiders. Allies of the Democratic nominee point to the foundation's global acts of charity when the organization has come under fire.

Hillary Clinton's own paid speeches became a magnet for criticism during the Democratic primary. Her acceptance of several six-figure speaking fees from Goldman Sachs in between her State Department service and the launch of her presidential campaign caused many progressives to question the authenticity of her anti-Wall Street rhetoric.