The emails also shed light on another of Mr. Nikolaev’s ventures, one that intersected with Ms. Butina’s efforts to cultivate the N.R.A. In December 2015, she accompanied an N.R.A. delegation that included its former president, David Keene, on a visit to Orsis, a Russian gun maker that sells sniper rifles to the Russian National Guard.
There they met Svetlana Nikolaeva, Mr. Nikolaev’s wife, who is the head of Orsis’s parent company, Promtechnologies Group. The 2013 business plan for the night-vision project stated that Mr. Nikolaev “controls the Promtechnologies Group who owns Orsis brand,” and that Promtechnologies “is ready to buy significant amounts of the project products.”
At various times, Promtechnologies executives have included Alexander Beseda, another son of the F.S.B. general, and Alexey Rogozin, the son of the former deputy prime minister. The elder Mr. Rogozin, who is subject to Western sanctions, also met with the N.R.A. group during its trip to Moscow with Ms. Butina.
Mr. Nikolaev’s spokesman said that the billionaire’s involvement in the company ended in 2014, and that it was “a free-standing commercial business unconnected to the Russian government.” He added that Alexander Beseda and Alexey Rogozin worked there “only briefly” and left in 2012.
The Beseda emails also contained documents pertaining to ScanEx, a Russian satellite-monitoring service in which Mr. Nikolaev became a major investor in 2014, along with Mr. Rotenberg, the son of Mr. Putin’s friend. Mr. Beseda appeared to be advising ScanEx on potential contracts with the Russian government, including the F.S.B. and the G.R.U., a Russian intelligence agency.
A letter written in Mr. Nikolaev’s name cited ScanEx’s government clients, saying the firm had a license from “the F.S.B. for carrying out works related to the use of information classified as state secret.” The spokesman said such licenses were “standard” for businesses that gathered “geographical data for commercial use.”
“It is not an indication of a tie to Russia’s security services,” he said.