Back in June, a tantalizing set of reports from Shane Harris of the Wall Street Journal gave us one indication that collusion may have occurred, or was at least attempted, between supporters of Donald Trump’s 2016 presidential campaign and Russian hackers who targeted Democrats’ emails.

And the reports raised serious questions about whether fired National Security Adviser Michael Flynn was involved in these efforts to contact hackers — questions that, per a new report by Harris published this Friday, special counsel Robert Mueller is looking into.

At issue is an effort by Peter Smith, a Trump-supporting GOP operative and private equity executive, to track down Hillary Clinton’s infamous 30,000 or so deleted emails during the fall of 2016.

The effort, described on the record to Harris by Smith (the 81-year-old man died a week and a half after their interview), entailed outreach to several hacker groups, including at least two that Smith believed to be Russian-tied, to see if they had hacked the emails and could release them.

The emails — which Clinton said she deleted because they were personal and unrelated to her work as secretary of state — never surfaced. And Smith didn’t work for the Trump campaign.

But there is a potential connection to the campaign — through Flynn. Smith repeatedly claimed that he was in contact with Flynn about the effort to find Clinton’s emails, per Harris’s sources:

“He said, ‘I’m talking to Michael Flynn about this — if you find anything, can you let me know?’” said Eric York, a computer-security expert from Atlanta who searched hacker forums on Mr. Smith’s behalf for people who might have access to the emails. ... ... In phone conversations, Mr. Smith told a computer expert he was in direct contact with Mr. Flynn and his son, according to this expert. ... The expert said that based on his conversations with Mr. Smith, he understood the elder Mr. Flynn to be coordinating with Mr. Smith’s group in his capacity as a Trump campaign adviser.

Harris also described, apparently for the first time, US intelligence reports claiming Russian hackers discussed how to get hacked emails to Flynn through a third party.

Investigators have examined reports from intelligence agencies that describe Russian hackers discussing how to obtain emails from Mrs. Clinton’s server and then transmit them to Mr. Flynn via an intermediary, according to U.S. officials with knowledge of the intelligence.

All this clearly raises serious questions about just what Flynn knew about this or any other attempted outreach to Russian hackers.

Further details on Smith’s effort were revealed in a June article on Lawfare published by information security expert Matt Tait and called “The Time I Got Recruited to Collude with the Russians.”

In the article, Tait described briefly working with Smith in his effort to obtain Clinton’s deleted emails. He wrote that his impression was that “it was immediately apparent that Smith was both well connected within the top echelons of the campaign and he seemed to know both Lt. Gen. Flynn and his son well.” He continues:

The combination of Smith’s deep knowledge of the inner workings of the campaign, this document naming him in the “Trump campaign” group, and the multiple references to needing to avoid campaign reporting suggested to me that the group was formed with the blessing of the Trump campaign.

However, Tait — an information security expert who tweets under the handle “Pwnallthethings” — acknowledged that he has no further proof of this.

How this story fits into the timeline of the hackings

It’s no secret that Trump wanted someone to find Clinton’s deleted emails — he said as much publicly.

To recap: When word got out that Clinton had used a personal email account for all her work at the State Department, she agreed to hand over the work-related emails on that account to government investigators. But it turned out that she had previously deemed about 32,000 emails (about half of the total) to be “personal” rather than work-related, and deleted them.

Many conservatives didn’t take Clinton’s explanation for why she deleted the emails at face value, and questioned whether the deleted emails could have included some incriminating information that might reveal scandalous behavior of some kind. One of those Republicans was Trump, who repeatedly referenced the deleted emails on the campaign trail.

In July 2016, hacked emails from the Democratic National Committee were publicly released, and the hacks were thought to be the work of Russia. And at the time, Trump said in public that he hoped there would be email releases to come — including Clinton’s deleted ones.

“Russia, if you’re listening, I hope you’re able to find the 30,000 [Hillary Clinton] emails that are missing,” he said at a press conference. “I think you will probably be rewarded mightily by our press. Let's see if that happens. That will be next.”

A few months after this, in fall 2016, Peter Smith launched the effort reported by the Journal to try to get the emails from hacking groups that he thought might have them — including hacking groups he understood to be tied to the Russian government.

Again, though, it seems that no one did have Clinton’s deleted emails. The biggest Russia-linked email hacks and dumps involved the DNC accounts (released in July 2016) and Clinton campaign chair John Podesta’s emails (released in October 2016), but no emails from Clinton’s own server.

Michael Flynn’s potential involvement could be highly significant

Still, one major question has always been whether any Trump associates were involved in these or other hacking efforts.

There’s been a whole lot of evidence that several Trump associates (including Flynn) had ties to Russian officials, and of course it was clear that Trump’s public policies were far more pro-Russia than the Republican norm.

But there really hasn’t been very much evidence tying anyone in Trumpworld to any hacking — making it plausible that the hacking operations were carried out without any coordination or contacts with anyone in Trump’s camp.

Harris’s reports have changed that somewhat, telling us about Smith’s outreach to Russian hackers — and, more importantly, Smith’s claims that Flynn (who was close to Trump) may have known too. And there’s that other claim that US intelligence suggests Russian hackers were discussing giving hacked emails to Flynn. Where would they get that idea?

Any involvement from Flynn could be quite significant. He’s known to have had many contacts with Russian officials, and he advised Trump on foreign policy matters during the presidential campaign.

Afterward, Trump named him national security adviser. But he didn’t last long in the post, resigning in February due to controversy over whether he falsely described his contacts with Russian Ambassador Sergey Kislyak during the transition.

By then, the White House had been told that Flynn was under federal investigation. And then-FBI Director James Comey has since testified that the day after Flynn’s firing, President Trump took him aside and told him, “I hope you can see your way clear to letting this go, to letting Flynn go. He is a good guy. I hope you can let this go.”

So Trump has already been trying to shield Flynn from investigators — making the question of just what Flynn might know ever more interesting, and one that special counsel Robert Mueller’s mind appears to be trying to get to the bottom of.