The signature of Trump’s eldest son is on two of them.

The eight checks bolster the outlines of the story Cohen has told. He recently testified that during the campaign, Trump knowingly entered into a conspiracy with him to buy the silence of Stormy Daniels about an alleged affair, a criminal violation of campaign finance laws at Trump’s direction, and then reimbursed Cohen throughout 2017, while Trump was president.

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Two of the checks came from a trust and thus were signed by Trump Organization chief financial officer Allen Weisselberg and Trump Jr.

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In a remarkable coincidence, the Times reports that one of the checks signed by Trump Jr. was issued on the same day that a Trump aide confirmed that the president had helped dictate a statement by Trump Jr. falsifying the rationale behind the infamous 2016 Trump Tower meeting. At that meeting Trump Jr. eagerly tried to conspire with Russia to corrupt our election on his father’s behalf.

That confluence of events neatly captures the seamy role that Trump Jr. has played throughout this whole affair, on multiple fronts.

Trump Jr.’s legal exposure remains unclear

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Legal experts I spoke with say the significance of Trump Jr.’s involvement in the hush-money scheme remains uncertain. One question is whether Trump Jr. was involved in the original conspiracy in the fall of 2016 to pay the hush money and whether he understood the payments as campaign expenditures.

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Cohen has declared that Trump fully understood these payments in these terms, and prosecutors have charged that Cohen carried them out at Trump’s “direction,” violating campaign finance laws, which is why Trump may end up getting charged after he leaves office.

But what about Trump Jr.?

Bob Bauer, the White House counsel under President Barack Obama, points out that Trump Jr. was a senior campaign official and may have been involved in discussions over the need to keep affairs alleged by Daniels and Karen McDougal under wraps for campaign purposes. Indeed, prosecutors have charged that Cohen “coordinated” these actions with “one or more members of the campaign.”

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“If Trump Jr. was acting on behalf of the campaign and involved in the conversation about the importance to the campaign of keeping this quiet, then he’s in the circle of co-conspirators,” Bauer told me, though he repeatedly stressed that we know very little about what happened.

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Then there’s the question of what Trump Jr. knew about the original payments when he signed the checks in 2017 reimbursing them.

“If he was aware of the purpose of the payments, then I think he could be on the hook for conspiracy to violate campaign finance laws,” former U.S. attorney Barbara McQuade told me. McQuade added that in this scenario, Trump Jr. would know that he and his father need to reimburse the payments in “installments, so as not to draw attention” to the payments and their original purpose of avoiding damage to the campaign.

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The question, McQuade said, is whether Trump Jr. “knew that was the scheme.” He may have just signed the checks without a full sense of why Cohen was getting reimbursed. “It really comes down to his knowledge and intent,” McQuade noted, adding that Weisselberg (who was granted limited immunity to testify about the payments) might shed light on that.

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If Trump Jr. does have exposure, then the question would be why prosecutors haven’t charged him yet. “It may be that they’re not done investigating or are looking for additional participants,” McQuade said. “It may be that they have other crimes or defendants they’re thinking of including.” Or it may be nothing.

Trump Jr.’s role in Russiagate remains cloudy

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Cohen testified that reports of the Trump Tower meeting with the Russians spurred him to remember an episode in which Trump Jr. may have told his father about the meeting in advance.

We have no idea whether this is true. But former Trump adviser Stephen K. Bannon has said: “The chance that Don. Jr. did not walk these Jumos up to his father’s office on the 26th floor is zero.”

Here’s what we do know: Trump Jr.’s own emails show that he eagerly wanted to conspire with a foreign power’s efforts to sabotage U.S. democracy, and he followed up by holding a meeting in pursuit of that end in his father’s signature skyscraper. He and his father subsequently issued a statement lying to America to cover this up.

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It’s fitting, in a way, that this act was confirmed on the date that one of these checks was issued. Because the bottom line on all this is that Trump had illicit help in getting elected president in two ways — from both the criminal scheme Cohen carried out, allegedly at Trump’s direction, and from Russia’s wide-ranging plot to corrupt our democracy, on Trump’s behalf. And Trump Jr. had at least some involvement, however limited, in both.

Even if not a single additional criminal charge is brought, all of that will remain true.

There is probably no one in Trump’s orbit who spends more time aggressively taunting the president’s critics and pursuers than Trump Jr. does. In so doing, he often seems to be daring the fates to come at him with a brash confidence that he will skirt any consequences, even as emerging facts seem to implicate him ever more deeply in multiple aspects of his father’s wrongdoing and alleged criminality.

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Whether that confidence amounts to hubris that will ultimately bring him down remains to be seen.