The timing of Michael Cohen's plea deal, Microsoft's Russian hacking allegations, and Paul Manafort's alleged ties to Russia raise some serious questions about Russia and the Trump campaign, former Assistant Attorney General of National Security John Carlin told CNBC on Tuesday.
"I don't think there's been a time in American history where we have had this many people this close to a presidential campaign politically tied up with one of our top adversaries," Carlin said on CNBC's "Power Lunch."
During his hearing, Cohen admitted to tax and bank fraud, as well as illegal campaign contributions at the direction of a candidate who was not named — although it was evident that this candidate was Trump.
Carlin, who has served as a top-level official in both Republican and Democratic administrations and now chairs a cybersecurity program at The Aspen Institute, did not assert Cohen's violations are in any way tied to Russia, but he said Trump's former lawyer "is certainly in a position to know a lot of information."
Former federal prosecutor Jacob Frenkel said, inherent to Cohen's guilty plea, will be a government expectation that he will cooperate with any investigations of interest.
"Everything is really going to turn on what Cohen can say about what did the president and people close to him actually know," Frenkel said Tuesday on "Power Lunch." "Fundamentally for Michael Cohen this is about bringing closure. And the government's expectation in that process is going to be his cooperation in whatever investigations may be of continuing interest to the government."
On Tuesday, Microsoft said it uncovered new Russian hacking attempts targeting U.S. political groups ahead of the midterm elections. Microsoft said a hacking group tied to the Russian government created fake internet domains that appeared to spoof two American conservative organizations. Russian authorities have denied those allegations.
"The Microsoft report was significant in that it's another data point that shows [Russia doesn't] care if you are a Republican or a Democrat or conservative or liberal think-tank, they are [against] our values and in favor of Putin's values," Carlin said.
Meanwhile, jurors convicted former Trump campaign manager Paul Manafort on eight felony charges late Tuesday afternoon. He was accused of hiding income, some of it from pro-Russian political sources.
"This has to do with whether or not Russia is trying to influence our campaign — and everyone agrees that they are — and then, secondly, were they trying to influence certain officials to do it and that Manafort may be one of those people," Carlin said.
Carlin said the timing of all these events is just too convenient.
That Cohen's guilty plea "is occurring at the same time that the former campaign manager is awaiting a jury verdict about his fraud, and interesting news today from Microsoft about Russia's continuing attempts to attack our country ... we have, I think, a confluence of events here of historic proportions," Carlin said.
The White House did not immediately respond to CNBC's request for comment.