In lobbying for a presidential permit to construct a massive oil pipeline stretching from Canada to the Gulf Coast, TransCanada’s Paul Elliott has tried nearly every angle.

Elliott — who served as Secretary of State Hillary Rodham Clinton’s national deputy campaign manager in 2008 — sought to broker multiple meetings between senior State Department officials and TransCanada executives. He offered to enlist Trans­Canada officials’ aid in helping State officials forge an international climate agreement. And he deluged administration officials with letters testifying to the virtues of the Keystone XL expansion project, which would ship crude oil from Canada’s oil sands region to American refiners.

The State Department, which completed its environmental assessment of the project last month, has indicated that it will decide later this year whether to allow the company to construct the 1,700-mile pipeline. across the U.S.-Canada border.

More than two dozen State Department e-mails obtained by the advocacy group Friends of the Earth under a Freedom of Information Act request provide an unusual glimpse into the lobbying for the Keystone permit, which has become a battleground in the national debate over how to address climate change.

They show how Elliott tried to exploit relationships built in political campaigns, with mixed results. The e-mails are almost all between Elliott and a special assistant to Cheryl Mills, Clinton’s chief of staff. All three knew one another from working on Clinton’s presidential campaign.

Damon Moglen, who directs Friends of the Earth’s climate and energy project, said the e-mails also show a State Department official giving inappropriate “coaching” to TransCanada’s chief executive about how to respond to arguments against the pipeline.

State officials countered that the messages show that TransCanada lobbyists and executives were diverted to officials not directly involved in the pipeline decision. “We don’t want to give anyone an unfair advantage by giving them access to a decision maker,” said Daniel Clune, principal deputy assistant secretary for the Bureau of Oceans, International Environmental and Scientific Affairs.

Environmentalists have urged the administration to block the permit on the grounds that tapping crude from Canada’s oil sands, or tar sands, releases far more greenhouse gases than other forms of oil extraction and could lead to spills in sensitive areas along the pipeline’s route. The project’s backers say it will provide foreign oil from a trusted ally while generating American jobs.

Trying to ease concerns

The e-mails show that Elliott worked assiduously to try to ease administration concerns about the pipeline’s environmental impact.

Much of the correspondence focuses on TransCanada’s dealings with David L. Goldwyn, who was U.S. special envoy on energy before leaving in January to become an energy consultant. Goldwyn did not play a role in the department’s environmental assessment of the project, though if he had stayed on, he would have weighed in on a still-pending review of whether the project is in the U.S. national interest.

In one e-mail dated June 28, 2010, Elliott wrote that he learned from a colleague that his company had “been directed by professionals who work for David Goldwyn to try to provide an assessment of the impact to my organization if the State Department were to withhold approving a presidential permit for a period of up to two (2) years.”

When Mills’s assistant, Nora Toiv, asked Goldwyn about the matter less than an hour later — noting that she and Mills were colleagues with Elliott on Clinton’s presidential campaign — he replied: “The issue is whether they would still produce the oil if we did not permit the pipeline. If so the emissions would be produced anyway. If not then denying the permit forestalls those emissions.”Referring to the environmental impact statement, or EIS, that the State Department was preparing at the time, Goldwyn continued, “That is what they need to address on the record, so it cane [sic] responded to in the EIS and national interest decision.”

In another e-mail more than a month earlier, on May 19, Elliott wrote that TransCanada’s president and chief executive at the time, Hal Kvisle, had a “very productive” meeting with Goldwyn and other State officials.

“David provide [sic] us with insight on what he’d like to see by way of on the record comment during this public comment period of this Keystone KXL draft environmental impact statement,” the lobbyist wrote. “We are working with our stakeholders, shippers and vendors to deliver on the insight David shared with us and to do so by the June 15 deadline.”

In its final environmental impact statement released last month, the department concluded TransCanada would exploit oil sands crude, whether or not the pipeline goes forward.

Goldwyn said in an interview that “I was not part of the process” for the Keystone environmental impact statement.

As a result, Goldwyn said,he “saw anybody and was willing to see anybody who had an interest in this,” including TransCanada’s chief executive, environmental groups and Canadian government officials. “My approach with all of them was to understand their arguments, explain the process and then present the counter-arguments to their arguments,” Goldwyn said.

When TransCanada executives wondered how anyone could oppose the pipeline, Goldwyn said he told them, “The issues that were on the table, which they needed to address on the record and not just with State Department interlocutors, were on the environment.”

“This was technically not in David’s purview,” said former State Department spokesman P.J. Crowley. “David had an interest in it but . . . he was not involved in the decision-making process.”

TransCanada spokesman Terry Cunha said the exchange — along with the other e-mails released by the State Department — simply shows the company’s consistent approach.

“It’s what we’ve always been highlighting for the past three years: energy security, a safe, secure stream of crude oil and job creation,” Cunha said, adding that Elliott sought meetings with senior State officials “to get our message across on the importance of the project” in light of environmentalists’ opposition.

The e-mails show Elliott pressed repeatedly for Mills to meet senior TransCanada officials — a request State rebuffed multiple times. On July 14, 2010 several State Department officials discussed Elliott’s request that Mills meet with TransCanada’s president for energy and oil pipelines, Alex Pourbaix. “Well, conveniently she’ll be out of town,” wrote Jacob Sullivan, who then served as deputy chief of staff and now directs the Office of Policy Planning.

One senior department official, who spoke on the condition of anonymity because the final permit decision is pending, said of Elliott: “He was a regular requester of meetings. We sometimes met with him, and he was sometimes told the person he was trying to meet with couldn’t meet with him.”At one point, Elliott suggested that his firm could lobby the Canadian government on the administration’s behalf. In an e-mail dated Dec. 6, 2009, Elliott offered to help State officials enlist Canada’s aid in securing a global climate accord during U.N.-brokered talks in Copenhagen.

“TransCanada’s senior executive leadership team would welcome any guidance you might share on background — U.S. government messaging and expectation — specific to developments at the United Nations Climate Change Conference in Copenhagen,” Elliott wrote to Mills’s assistant. “If there is a message and or topics that the State Department would welcome us to encourage with Canadian government officials, I am happy to pass on that direction to the senior executive leadership team of TransCanada. TransCanada can be an asset for the state department and I hope you might see us as such.”

Cunha denied that Elliott was suggesting the firm could help the administration at international climate negotiations. Instead, Cunha said, Elliott “was trying to understand what impact these policies would have on our natural gas assets.”

Moglen said that Friends of the Earth would pursue additional documents. He said the documents released were numbered, but some numbers were missing. “There are clearly things that are not here,” he said. He also questioned why Elliott did not register as a lobbyist for a foreign company until Dec. 16, 2010 even though he was approaching State officials about the project more than a year earlier. Cunha said Elliott’s activities did not warrant a formal registration until “the last six weeks of 2010.”

Moglen said the June 28 e-mail exchange suggests department officials gave TransCanada special access to what is supposed to be an impartial process.“That is obviously not an independent, probing environmental review process,” Moglen said in an interview. “It’s, in fact, a closed loop.”