With his Fifth Avenue-redneck persona and his affinity for the alt-right, Donald Trump, Jr., has sometimes been described as a chip off the old block. But his relationship with his father hasn’t always been a smooth one.

When Trump, Jr., was twelve, his father left his mother, Ivana, for a much younger woman, Marla Maples. It has been widely reported that Trump, Jr., stopped talking to his father for a time after that. They reportedly had some run-ins later on, too, when Trump, Jr., was enrolled at the University of Pennsylvania. “Don Jr. opened the door, wearing a Yankee jersey,” Scott Melker, one of his former classmates, wrote on Facebook last year, describing what happened on one occasion when Trump came to take his son to a Yankees game. “Without saying a word, his father slapped him across the face, knocking him to the floor in front of all of his classmates. He simply said “put on a suit and meet me outside,’ and closed the door.” (The Trumps have denied this account.)

After graduating, Trump, Jr., spent some time as a ski bum in Colorado. But eventually he joined the family business, and this apparently improved the father-son relationship. In dynastic fashion, he ascended rapidly. During his father’s Presidential run, he took an active role in the campaign. At last year’s Republican National Convention, Trump, Jr., delivered a speech that culminated in his statement that America needed a President “who will unleash the greatness in our nation and in all of us. . . . That president can only be my mentor, my best friend, my father, Donald Trump.”

After the election, the plan was for Trump, Jr., to stay behind in New York and run the family business with his younger brother Eric Trump. But that’s not how things have worked out. During the past few months, Trump, Jr., has become thoroughly embroiled in the investigation that the special counsel Robert Mueller is conducting into Russian interference in the 2016 election, and he’s already been hauled up to Capitol Hill to testify before a Senate committee. When President Trump gets back to Washington on Tuesday night, following his lengthy trip to Asia, one of the first things he will be asked about is his eldest son, who is once again in the soup—right up to his throat this time.

On Monday, Julia Ioffe, of The Atlantic, revealed that, during the final weeks of last year’s campaign, Trump, Jr., corresponded via direct messages on Twitter with WikiLeaks, which was then busy posting e-mails that had been hacked from the personal account of John Podesta, Hillary Clinton’s campaign chairman. According to Ioffe’s article, Trump, Jr., also sent an e-mail informing other people on the campaign—including Steve Bannon, Kellyanne Conway, and Jared Kushner—about this contact.

Evidently, Donald Trump himself wasn’t included in this e-mail chain, but he has been implicated indirectly in this chain of events. Shortly after Ioffe’s piece appeared, the Wall Street Journal’s Byron Tau pointed out that on October 12, 2016, just fifteen minutes after WikiLeaks sent Trump, Jr., a message suggesting that his father should tweet out a link to a WikiLeaks search tool, Trump tweeted, “Very little pick-up by the dishonest media of incredible information provided by WikiLeaks. So dishonest! Rigged system!”

It should be noted that there is currently no proof that Trump, Jr., informed his father about his contacts with WikiLeaks. But the timing is certainly suggestive. “I suppose you could say it was mere coincidence that Trump tweeted about WikiLeaks 15 minutes after the organization asked his eldest son for him to do just that,” CNN’s Chris Cillizza noted on Tuesday. “But, that would be one hell of a coincidence given the timing of the tweets and the fact that we know . . . that Don Jr. let the senior staff of the campaign know that WikiLeaks had made contact back on September 21.”

Those fifteen minutes aren’t the only troublesome timing issue for Trump and Trump, Jr. On October 7th, just five days earlier, the Department of Homeland Security and the Office of the National Intelligence Director had issued a joint statement, saying, “The U.S. Intelligence Community (USIC) is confident that the Russian Government directed the recent compromises of e-mails from US persons and institutions, including from US political organizations.” Referring directly to WikiLeaks, the statement went on, “These thefts and disclosures are intended to interfere with the US election process.”

All this raises serious questions about Trump, Jr.,’s actions. Foreign nationals are barred, by law, from interfering in a U.S. election by contributing something “of value” to a campaign. Any U.S. citizen who assists the perpetrator of such an action may be guilty of conspiracy, which, unlike the vaguely defined term “collusion,” is certainly a crime. Earlier this month, the Wall Street Journal reported that the Department of Justice is considering criminal charges against at least six Russians who it believes were involved in the hacking of the Democratic National Committee.

To be sure, none of this proves that Trump, Jr., broke any laws. The timeline as it is publicly understood suggests that Podesta’s e-mails were hacked well before Trump, Jr., corresponded with WikiLeaks, so there’s no suggestion he was complicit in that crime. But, under the federal Computer Fraud and Abuse Act, it can also be a crime to aid in the dissemination and public release of stolen material with knowledge and intent of furthering the underlying crime of unauthorized access to a protected computer or network.

The law here is somewhat murky—as a lengthy piece at the Lawfare blog helpfully explained in July. Also, Alan Futerfas, a lawyer for Trump, Jr., insisted in a statement to the Atlantic about the direct messages that he had “no concerns about these documents and any questions raised about them have been easily answered in the appropriate forum.” But this still looks like an avenue that Mueller and his colleagues will be eager to explore, just as they will be looking to find out what exactly happened in the now infamous meeting that Trump, Jr., held with a group of Russians at Trump Tower on June 9th of last year, which was set up with the promise of dirt on Hillary Clinton.

In short, Trump, Jr.,’s campaign activities have created a real problem for him and his father, and a public-relations disaster for the White House. Even though Roger Stone, a longtime Trump ally, boasted during the campaign about communicating with Julian Assange, and Trump himself repeatedly touted the hacked D.N.C. and Podesta e-mails—saying, on one occasion, “I love WikiLeaks”—the Trump camp has consistently and vehemently denied that it had any ties to the organization. Last October, while WikiLeaks was sending Trump, Jr., direct messages, a Fox News interviewer asked Mike Pence, who was then Trump’s Vice-Presidential candidate, whether the campaign was “in cahoots” with WikiLeaks. He replied, “Nothing could be further from the truth.”

On Monday night, after the Atlantic’s story appeared, a spokeswoman for Pence said that he was “never aware of anyone associated with the campaign being in contact with WikiLeaks. He first learned of this news from a published report earlier.” That is a pretty humiliating admission for the Vice-President to make; it appears that, in his earlier statements, he was either lying or being taken for a naïf.

As of Tuesday afternoon, the President hadn’t commented publicly about the latest Trump, Jr., firestorm, but in a tweet he did say that he “will be making a major statement from the @WhiteHouse upon my return to D.C. Time and date to be set.” Will he announce that Trump, Jr., was a foundling, or describe him as “a young, low level volunteer” and say that he “has already proven to be a liar”? (That was how he described George Papadopoulos, one of his former foreign-policy advisers, who is now a coöperating witness in the Mueller investigation.) Given Trump’s own interest in minimizing the WikiLeaks story, it seems more likely that he will describe his son, who is thirty-nine years old, as “a good boy . . . a good kid,” which is what he said in July, after the June, 2016, meeting at Trump Tower came to light.