Bob Woodward’s new reporting that former president Donald Trump has spoken to Russian President Vladimir Putin as many as seven times since leaving office raises all kinds of questions. Among them: What might they have talked about? Why the continued cloak-and-dagger on Trump’s talks with Putin? Did any such conversations continue after Russia invaded a U.S. ally, Ukraine, in February 2022, and pertain to that?

All are valid questions, given Trump’s provocative and often-cozy relationship with Putin.

And the significance of nearly all of those questions was quickly made clear, however unintentionally, by Trump running mate JD Vance.

“Even if it’s true, is there something wrong with speaking to world leaders? No,” Vance said Tuesday. “Is there anything wrong with engaging in diplomacy?”

JD Vance on the report that Trump had seven phone calls with Putin AFTER leaving the WH:

“Is there something wrong with speaking to world leaders? No. Is there anything wrong with engaging in diplomacy?” pic.twitter.com/qUORbZt1lS

— Republicans against Trump (@RpsAgainstTrump) October 8, 2024

There is, in fact, something potentially wrong — and potentially, technically, illegal — with a former official like Trump engaging in shadow diplomacy with Putin.

And none other than Trump himself has said as much, at least when it involved a Democrat. Trump not only pushed for but also apparently succeeded in getting a political opponent, former secretary of state John Kerry, investigated for alleged “shadow diplomacy.”

Given that, it would seem much more difficult for the Trump campaign to wave this off as a non-story.

Trump’s campaign on Tuesday broadly dismissed Woodward’s book as “made-up stories,” though Trump often falsely denies things that later prove to be true.

It’s one thing for Trump to have talked to Putin and another for this to have involved the word Vance invoked: “diplomacy.”

That could be illegal, under the letter of the law. The Logan Act bars unauthorized private citizens from engaging foreign governments with the “intent to influence the measures or conduct of” those countries, “in relation to any disputes or controversies with the United States or to defeat the measures of the United States.” Basically, you can’t seek to undermine the official foreign policy of this country by conducting your own diplomacy. If Trump offered guidance to Putin on his conduct in the war in Ukraine, that would be problematic.

But the Logan Act has never been successfully prosecuted, which was noted when it cropped up multiple times during Trump’s presidency. So it’s not as if Trump’s breaking the law is a particularly live issue.

What is a live issue, though, is the propriety of it. And Trump has made clear that he is against former officials speaking to adversarial foreign governments and undercutting American foreign policy.

Trump not only repeatedly accused Kerry of breaking the law by speaking to Iran during Trump’s presidency, he even pushed for Kerry’s prosecution. And a clear timeline of events suggests this had a real impact, resulting in Kerry’s being investigated by the Justice Department.

The Kerry matter was one of the most significant examples of Trump’s apparently weaponizing the government against his foes — something he has suggested he would do even more if he’s elected to a second term.

Trump’s criticisms of Kerry were spread out, but he repeatedly cited the idea that a former official engaging a hostile foreign country was wrong and even illegal:

“The United States does not need John Kerry’s possibly illegal Shadow Diplomacy on the very badly negotiated Iran Deal,” Trump tweeted in May 2018.
“John Kerry had illegal meetings with the very hostile Iranian Regime, which can only serve to undercut our great work to the detriment of the American people,” he tweeted in September of that year.
“You know, John Kerry speaks to them a lot,” Trump said at the White House in May 2019. “John Kerry tells them not to call. That’s a violation of the Logan Act. And, frankly, he should be prosecuted on that.”
“I think John Kerry shouldn’t have been speaking — that’s called the violation of the Logan Act,” Trump told Fox News in March 2020.
Trump Secretary of State Mike Pompeo attacked Kerry in September 2018, saying, “Actively undermining U.S. policy as a former secretary of state is literally unheard-of.” He called it “unseemly and unprecedented” to have a “former secretary of state engaged with the world’s largest state sponsor of terror” in this way.

Trump’s comments generally focused on the idea that Kerry had strategized with Iran about how to navigate Trump’s withdrawal from the Obama’s administration’s Iran nuclear deal or urged it to wait to negotiate with a Democratic administration. There’s no evidence Kerry actually did that, though, and Kerry denied coaching Iran on the subject. Kerry maintained that there was “nothing unusual … about former diplomats meeting with foreign counterparts.”

But Trump did apparently succeed in getting Kerry investigated.

Former U.S. attorney Geoffrey Berman wrote in his 2022 book that Trump’s Justice Department referred the case to his Southern District of New York in May 2018 after a pair of Trump tweets in the two days prior. The Justice Department checked in again right after an April 2019 Trump tweet, and then again the following day.

Berman called the pattern “clear — and outrageous.”

Much more is apparently known today about Kerry’s conversations with the Iranians than Trump’s reported conversations with Putin, given that investigation and the fact that Kerry talked at some length about what was discussed. Berman has called Kerry “innocent” and said two separate districts declined to prosecute Kerry.

Trump’s talks with Putin, meanwhile, have long been a black box.

That perhaps made some sense when Trump was president; official diplomacy often requires secrecy to work. But that doesn’t apply when you’re not actually supposed to be conducting diplomacy. And to the extent Trump might have been doing that with Putin, his own commentary on the subject would sure suggest we need to know more about it.

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