Rudolph W. Giuliani is now, for the second time, suggesting President Trump’s effort to secure a Trump Tower Moscow may have persisted into late 2016. Giuliani said last month that it was possible, and on Sunday he leaned into it even more strongly. He told the New York Times that Trump told him it was “going on from the day I announced to the day I won.” (Giuliani later walked this back, saying his comments were hypothetical and not based on conversations with Trump.)

This may seem like a bunch of quibbling over a very narrow point. What does it matter if the effort lasted into late 2016? Whether Trump was pursuing it during the general election or just during the GOP primary, he was still doing it while actual voters were voting.

But the timeline here is important, and it adds further intrigue to a question that has grown because of several recent reports: Has Russia ever had leverage over Trump?

The fact that Trump pursued a project in Russia even as voters were voting is problematic in and of itself — especially given Russia’s effort to assist in his victory. But the longer it lingered into late 2016, the more potential leverage Russia could have gained. That’s because the more time it covered, the more Trump’s denials about having business interests in Russia would be rendered false. And former Trump lawyer Michael Cohen’s plea deal with special counsel Robert S. Mueller III makes clear this is something the Kremlin would have been aware of, given Cohen was in contact with it about the project.

Cohen’s plea deal indicated that his efforts to land the deal continued “as late as approximately June 2016.” Here’s a quick timeline of what Trump said after that date, with an assist from The Washington Post’s Fact Checker team (emphases added):

  • July 26: “For the record, I have ZERO investments in Russia.” 
  • July 27: “I have nothing to with Russia, I have nothing to do with Russia. . . . I have nothing to do with Russia."
  • Later July 27: "I mean I have nothing to do with Russia. I don’t have any jobs in Russia. I’m all over the world, but we’re not involved in Russia.”
  • Oct. 9: "I know about Russia, but I know nothing about the inner workings of Russia. I don’t deal there. I have no businesses there. I have no loans from Russia.”
  • Oct. 24: "I have nothing to do with Russia, folks. I’ll give you a written statement.”
  • Oct. 26: "First of all, I don’t know Putin, have no business whatsoever with Russia, have nothing to do with Russia.”

All of these answers were misleading, at best, from a president whose lawyer was still pursuing a Trump Tower Moscow in 2016 — even if those efforts stopped in June. But you’ll note that almost of them are in the present tense (“I have nothing,” “I don’t deal there,” “We’re not involved”). If the efforts stopped in June, they are perhaps more defensible. But if they continued into late July, Trump’s repeated “I have nothing to do with Russia” would be very difficult to reconcile. If they persisted until near Election Day, “I don’t deal there” would be likewise.

None of this is to say Russia ever tried to use such leverage — and for the record, Trump denied in January 2017 that it had — but leverage exists whether it’s used or not. And this is merely the latest hint of the potential for it in recent weeks.

The New York Times reported a couple of weeks back that the FBI launched a counterintelligence investigation shortly after Trump fired FBI Director James B. Comey to look into whether Trump was working for Russia. The next day, The Washington Post’s Greg Miller reported that Trump has gone to great lengths to conceal the details of his five meetings with Russian President Vladimir Putin. Trump even at one point took the notes of the interpreter from his two-hour, closed-door meeting with Putin and told the interpreter not to discuss what was said with anyone, including in his administration.

We still have almost no concept of what was said in those meetings, but the Russians do. That doesn’t mean Trump said anything that could give leverage to Putin — who by the way is a trained former intelligence agent with the KGB — but we apparently may never know for sure.

And Trump’s history here looms large. This is the president who blurted out highly classified information during an Oval Office meeting with top Russian officials. This is a president who reportedly insists on using an unsecured cellphone even though Russia is listening in. And this is a president who has a penchant for saying false things and admitting things he probably shouldn’t. That’s not exactly a recipe for assurance that he was careful when talking to Putin.

The question of Russia and leverage marred the early days of the Trump administration — but not when it came to Trump. At the time it was about national security adviser Michael Flynn, whose lies about his conversations with the Russian ambassador meant the Russians knew something they could have used to exert leverage. This so concerned then-acting Attorney General Sally Yates that she warned the White House about this possibility. The White House waited 18 days to fire Flynn.

The parallels to Trump are evident, even as the leverage in his case hasn’t been proved. But Trump’s own legal spokesman on Sunday allowed for a timeline that could mean Russia would know about Trump’s false statements in a way Americans didn’t. And Trump hasn’t exactly gone to great lengths to disprove something the FBI came to suspect.

Democrats are starting to sniff around this question. Expect to hear more about it in the months to come.