With the Obama administration about to decide whether to green-light a controversial pipeline to take crude oil from Canada’s oil sands to the United States Gulf Coast, e-mails released Monday paint a picture of a sometimes warm and collaborative relationship between lobbyists for the company building the billion-dollar pipeline and officials in the State Department, the agency that has final say over the pipeline.

Environmental groups said the e-mails were disturbing and evidence of “complicity” between TransCanada, the pipeline company, and American officials tasked with evaluating the pipeline’s environmental impact.

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