The most concerning question involving Acting Attorney General Matthew Whitaker’s relationship to Sam Clovis, the national co-chairman of the 2016 Trump campaign, has been missed by many. It’s not simply that the two are friends or that Whitaker was the chairman of Clovis’ own campaign back in 2014 for state treasurer in Iowa. Rather, the two men’s relationship, particularly during the presidential campaign, raise potentially far more significant conflicts of interest than even Whitaker’s prior public statements critical of the Mueller investigation.

I. Connections to the Trump Campaign

First, Whitaker may have served as something like an informal adviser to the Trump campaign. Clovis recently told Reuters that Whitaker was a “sounding board” for him when Clovis worked for the Trump campaign. To realize the full importance of that statement, and just how problematic it is, one has to understand Clovis’ role on the campaign. Whitaker was not advising just some random, low-level official. Alongside, Paul Manafort, Clovis served as co-chairman of the Trump Campaign. Clovis also assembled the campaign’s national security group headed by Jeff Sessions, and reportedly was involved in bringing on board George Papadopoulos and Carter Page. Depending on what information Clovis shared with Whitaker in using him as a sounding board, Whitaker might be best described as a campaign insider.

It’s currently unknown what advice Clovis sought from Whitaker, whose main expertise would have likely been as a former US Attorney. We do know one instance in which Clovis referenced, in an internal campaign email with other campaign officials, to legal concerns raised by a potential meeting with Russians and Trump. The proposed meeting arose out of Papadopoulos’ correspondence with Russian agents. “There are legal issues we need to mitigate, meeting with foreign officials as a private citizen,” Clovis wrote in the email.

II. Communications with a grand jury witness

Second, Whitaker has apparently engaged in frequent private communications with a key grand jury witness while, at the same time, serving as Chief of Staff to then-Attorney General Jeff Sessions. That witness: Sam Clovis. Whitaker began his work as chief of staff in late September 2017. Clovis testified before the grand jury in October 2017. The fact that Clovis was a grand jury witness became public that same month. The White House first learned from the news media that Clovis had testified before the grand jury. Unlike other members of the White House staff, Clovis had not informed the President’s legal team. The two men–Whitaker and Clovis–then continued to correspond regularly with on another after Whitaker must have known Clovis was a grand jury witness. In an interview last week, Clovis said that “he and Whitaker have kept up, and regularly still text one another, as recently as within the last few weeks.” But then just how central is Clovis to the Mueller investigation?

Clovis is “an important witness in the Russia probe,” Rep. Adam Schiff (D-Calif.), the incoming chair of the House Intelligence Committee, wrote. That’s no exaggeration. Just look to Papadopoulos’ plea documents provided by Mueller in federal court. Clovis served as Papadopoulos’ supervisor. When Papadopoulos told Clovis of his initial contacts with the Russians, Clovis was very supportive, telling the young national security adviser “Great work.” Papadopoulos later proposed to arrange a back-channel, “off-the-record” meeting between Trump campaign representatives and senior Russian officials. In June 2016, when Papadopoulos emailed Paul Manafort about his efforts with the Russians, Manafort referred him to Clovis who Manafort described as “running point.” You read that right. In mid-August 2016, Clovis instructed him: “I would encourage you” and another foreign policy advisor to the Campaign to “make the trip[], if it is feasible.” Three days after Papadopoulos’ guilty plea was made public, Clovis withdrew from consideration for a Senate-confirmed position in the administration; his nomination hearing was already scheduled and would have taken place the following week.

Making this situation even more problematic is the fact that Clovis reportedly advised Whitaker on how to get a job in the Trump administration, a strategy that involved Whitaker going on national television and disputing allegations of collusion and the legitimacy of the Russia probe. This reportedly succeeded with Trump who “liked what he saw.” So Clovis, now a grand jury witness, also advised Whitaker in getting his job at the Justice Department. It would be important to know whether Clovis also recommended Whitaker to Sessions for the position of chief of staff (since one of Whitaker’s most recent jobs on his resume was the work for Clovis, and Clovis knew Sessions from their work together in the 2016 campaign).

III. Implications for overseeing the Russia probe

When I first read that Whitaker had worked as campaign chairman for Clovis’ run for Iowa state treasurer in 2014, it caught my attention but did not overly concern me. But these later revelations, one in the interview with Reuters and the other in an interview with Talking Points Memo, do.

It may be more of a judgement call whether the pair’s friendship (Clovis says they are “very close friends”) and Whitaker’s work for Clovis in 2014 are sufficient cause for recusal (I have my doubts). But serving as an informal adviser to Clovis during the 2016 presidential campaign would be a clear red line. The same Justice Department rules that precluded Sessions from overseeing the Russia investigation, because of his ties to the Trump campaign, would apply to Whitaker.

Depending on the content of the communications between Whitaker and Clovis while Whitaker was Sessions’ chief of staff, that second set of issues could raise a host of other ethical issues. The burden is on Whitaker to resolve these problems. In the meantime, he should certainly not oversee the Russia probe.