When former FBI Director James Comey testifies on June 8, he can expect to get this question (especially from some Republican senators): If you thought President Donald Trump was inappropriately pressuring you to end the Russia investigation, did you report that behavior to anyone? If not, why not? Those questions are important with respect to Comey’s credibility and because his failure to report to specific authorities may be construed as an indication that the president’s actions were not that problematic.

In anticipation of that question, here’s a look at what Comey’s options were for reporting wrongdoing by the president and how they narrowed over time. (As for the side issue of whether Comey was legally obligated to report Trump’s actions, several legal experts have said: no. As Just Security’s Andy Wright told Business Insider, “[Comey] might have had some sort of legal ethics requirement to do so but that’s not the same thing as violating a criminal statute.”)

Who Was in Place When?

The fluctuating leadership at the top of the Justice Department, plus the potential for conflicts of interest for people like Attorney General Jeff Sessions and others would have clearly complicated Comey’s choices, said Michael German, a fellow with the Brennan Center for Justice and former special agent with the FBI.

“In a normal situation, Comey should have reported his concerns to the attorney general and the deputy attorney general, and perhaps to the U.S. Attorney overseeing the investigation, depending on the circumstances,” German told Just Security. But nothing about this situation was normal, he added. 

During the roughly four months that Comey served as FBI director under Trump, three different people performed the duties of attorney general. The administration began with Sally Yates serving as acting attorney general until she was fired by Trump on Jan. 30. Dana Boente, U.S. Attorney for the Eastern District of Virginia, then filled in as AG until Jeff Sessions began the job on Feb. 8. Comey might not have seen Sessions, an early and ardent Trump supporter during the campaign, as an impartial repository for his growing concerns about Trump’s suggestions that he lay off the Russia investigation. If Comey had these worries about Sessions’ impartiality, they would have been confirmed by March 2, when Sessions recused himself from overseeing the Russia investigation after calls for his recusal by many, including members of Congress.

“Attorney General Sessions recused himself from the Russia investigation, so he could not be informed,” German said. “Sally Yates was fired as Deputy Attorney General, so U.S. Attorney Dana Boente was serving in that role in an acting capacity. This fact may have given Comey pause, but Boente was also leading at least some part of the Russia investigation in his role as U.S. Attorney for the Eastern District of Virginia, so he was probably an appropriate recipient anyway.”

If Comey didn’t have confidence confiding in the attorney general, he could have turned to the deputy AG: first Yates, then Boente, and then Rod Rosenstein. Yates and Boente were never going to be in the job for long. As for Rosenstein, Comey reportedly had concerns about him from early on, sharing them in a conversation with Lawfare’s Ben Wittes at the end of March. According to Wittes, Comey said, “Rod is a survivor. And you don’t get to survive that long across administrations without making compromises. So I have concerns.” Soon after starting at Justice, Rosenstein supplied the White House with a memo in which he provided Trump justification to fire Comey, knowing this was the president’s objective.

“If Comey argued he wanted to wait until an official deputy attorney general was sworn in, which Rod Rosenstein was at the end of April, I think that would be reasonable,” German said.

If Comey didn’t feel like he could confide in Justice Department leadership, he could have possibly reached out to the DOJ inspector general. Although, “the problem was not inherently internal to the Department,” Andy Wright said in an email to me. Finally, Comey could have reported Trump’s actions to Congress, but this, like the other options, was not risk-free either. Information shared with congressional leaders could leak to the press or make its way back to the White House.

“Reporting through the chain of command is always the best option, because it reflects the proper functioning of the agency,” German said. “Here, that chain was a little muddled, due to Attorney General Sessions’ recusal, but the deputy attorney general or acting deputy attorney general were certainly capable of fulfilling their responsibilities in this situation. If they received the Comey memos and did nothing, that should be a subject of further congressional inquiries.”

Wright, like German, said Comey’s best option would have been to report Trump’s actions to Justice Department leadership.

But until we hear from Comey, we don’t know if and when he felt Trump’s actions tipped the scales, moving from merely inappropriate or unethical behavior to something illegal or  criminal in nature like obstruction of justice.

“The moment at which Comey documented his conversations might not be a stand-alone offense,” Wright said.  “However the totality of circumstances sure looks like the corrupt intent necessary to support an obstruction of justice charge.”

If Comey ever thought a crime had occurred, meaning Trump was corruptly attempting to interfere in an FBI investigation, “Comey was obliged to document the event in official records and make sure it was preserved in FBI files for continuing investigation in the normal course of business, just as any FBI agent would. Of course nothing about this situation is normal,” German said.

Below is a brief timeline of the leadership changes at the Justice Department and the reported conversations between Trump and Comey to help see who was in their jobs when the events reportedly took place. Thank you to the BillMoyers.com website for its comprehensive timeline on Russia and Trump from which these key moments were pulled.

Timeline of Justice Department Leadership Changes and Comey-Trump Interactions

Jan. 14: The Washington Post reports that Rod Rosenstein is the Trump administration’s choice to replace Sally Yates as deputy attorney general.

Jan. 22: Comey attends a ceremony at the White House where he tries not to get specially noticed by the president.  The president calls out Comey and embraces him, expressing gratitude.

Jan. 27: Comey attends a one-on-one dinner with Trump, reportedly at the invitation of the president. Trump however told NBC on May 11 that Comey requested the dinner because he wanted to keep his job. The New York Times reported Trump turned the conversation to “whether Mr. Comey would pledge his loyalty to him.” Comey reportedly declined to make that pledge. In his interview with NBC, Trump admitted that he asked Comey whether he was under investigation. During that interview, Trump also said Comey told him three times that he was not under investigation. According to Trump, one of those times was at the dinner after the president asked him about it. Trump said Comey also assured him he was not under investigation during two separate phone calls, one the president made to him and one that Comey initiated.

Jan. 30: Sally Yates is fired.

Jan. 31: White House says it’s going to nominate Rosenstein as deputy attorney general.

Feb. 8: Jeff Sessions becomes attorney general.

Feb. 14: According to Comey’s memo, Trump asks Comey to halt the investigation into Michael Flynn during a private moment in the Oval Office after the president asked the attorney general and vice president to leave them alone in the room. “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.” According to the New York Times report, Comey “shared the existence of the memo with senior F.B.I. officials and close associates.”

Feb. 15: Comey told Attorney General Sessions that he did not ever want to be left alone again with the president.

Feb. 17: Comey meets in private session with members of the Senate Intelligence Committee reportedly to discuss the Russia investigation.

March 1: Comey is told the president wants to talk to him on the phone. Comey thought whatever it was, the matter must be urgent, but Trump just wanted to chit chat with him. Trump reportedly didn’t inquire about the Russia investigation during the call, but according to Wittes, with whom Comey discussed the call, Comey “perceived the call as Mr. Trump still ‘trying to get him on the team and he saw it in light of his refusal to give him his loyalty.’”

March 2: Sessions recuses himself from “any existing or future investigations of any matters related in any way to the campaigns for President of the United States.”

March 20: Comey testifies before the Senate Intelligence Committee, stating publicly for the first time that the FBI  is investigating Russian efforts at interfering in the election, including “the nature of any links between individuals associated with the Trump campaign and the Russian government and whether there was any coordination between the campaign and Russia’s efforts.”

March 27: Comey voices to Wittes over lunch his concerns with Rosenstein. As for his relationship with Trump, according to Wittes, “By the time we had lunch that day, Comey thought he had the situation under control. It had required a lot of work, he said, to train the White House that there were questions officials couldn’t ask and that all contacts had to go through the Justice Department. But he thought the work had been done.”

April 25: The Senate confirms Rod Rosenstein as deputy attorney general.

May 9: Trump fires Comey.

[Editor’s Note: In advance of Thursday’s hearing, be sure to read Ryan Goodman and Alex Whiting’s “How to Frame—and Not Misframe—Comey’s Testimony”]

Image: Zach Gibson/Getty Images