A trove of Justice Department filings sheds new light on James Comey’s final weeks as FBI director — a period marked by secret emails, internal tension, and a decision that would shake the 2016 election.
In the fall of 2016, as the presidential race between Hillary Clinton and Donald Trump entered its final, fevered stretch, the director of the FBI found himself standing at the center of a political storm. James Comey, then one of the most powerful law enforcement officials in the country, privately admitted he felt “unease” as he prepared to notify Congress that new Clinton-related emails had been found — a revelation that could shift the direction of the already volatile campaign.
“I hate having to do it,” Comey wrote in an email to his confidant, Daniel Richman, now made public through a newly filed Justice Department court record.
The message, simple yet heavy, offers a candid glimpse into Comey’s mindset at the moment the bureau’s internal actions would become front-page news — and ignite a firestorm that continues to shape U.S. politics nearly a decade later.
But today, Comey is no longer a central figure in a historic election fight. He is a criminal defendant, pleading not guilty as federal prosecutors accuse him of misleading Congress about media leaks related to the Clinton email investigation.
As his legal battle escalates, the Justice Department has released a series of newly disclosed messages showing the FBI director’s behind-the-scenes conversations during those tumultuous weeks — conversations that prosecutors say contradict his later sworn testimony.
Taken together, the documents paint a complex portrait: a director bracing for a Clinton victory, preparing for the political fallout of his decisions, and communicating in private through an anonymous Gmail account about matters he publicly insisted must remain strictly confidential.
The “October Surprise” That Never Really Surprised FBI Leadership
The new court filings revisit one of the most disputed moments of the 2016 election: Comey’s decision to inform Congress, just days before the vote, that newly discovered emails on Anthony Weiner’s laptop appeared relevant to the Clinton email investigation.
At the time, the move was described as an “October Surprise” — an explosive last-minute revelation that Republicans seized upon and Democrats harshly condemned.
But according to the Justice Department’s new records, top FBI officials had known for weeks about the emails.
Former FBI counterintelligence agent Peter Strzok — whose own texts later fueled accusations of political bias inside the bureau — had been aware since September 2016 that the Weiner laptop contained Clinton-related messages.
This detail undermines the public perception that Comey’s October letter was driven by sudden urgency. Instead, it suggests that the bureau was tracking the situation long before it became public — and that Comey’s internal concerns were less about new information and more about the potential political ramifications.
According to DOJ filings, Comey anticipated that Clinton would win.
In his message to Richman, he referred to the soon-to-be president as “president-elect Clinton.”
That belief — that Clinton’s victory was inevitable — shaped much of Comey’s approach, according to investigators. It explained his desire to “cover all bases” before she took office. It also heightened his anxiety about how the FBI’s actions would be perceived in hindsight.
The Private Exchanges: Comey’s Unease Comes to Light
The newly released correspondence between Comey and Richman — a longtime friend, academic, and sometime intermediary between Comey and the press — provides the clearest window yet into Comey’s thinking.
They show:
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Comey’s discomfort with sending the letter
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His expectation that Clinton would win
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His desire to avoid the perception of hiding information
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His active coordination with Richman about media fallout
Richman, at the time, was assisting the FBI during the election cycle, though he later became better known for providing Comey’s memos to The New York Times after President Trump fired him.
Prosecutors now argue that the Comey-Richman communication demonstrates that Comey was not the impartial actor he portrayed himself to be in later congressional testimony — particularly regarding media contacts.
The Federal Case Against Comey
Comey now faces federal charges alleging that he misled and obstructed Congress when he denied authorizing media disclosures during the Clinton email investigation.
The indictment alleges that:
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Comey used Richman as an intermediary to reporters
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He encouraged certain leaks to shape public perception
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He later denied authorizing those contacts
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He used an anonymous Gmail account to conduct FBI-related communications
Comey has pleaded not guilty, calling the charges politically motivated and an attempt to rewrite the history of his time at the FBI.
His attorney, Jessica Carmichael, filed a request asking the court to force prosecutors to provide a “bill of particulars” — essentially demanding greater detail about the specific allegations.
In her filing, Carmichael argued:
“Mr. Comey seeks specificity… The indictment in its current form does neither [inform the charges nor allow him to prepare a defense].”
The Justice Department pushed back forcefully.
Acting U.S. Attorney Lindsey Halligan argued that a bill of particulars is not meant to be a fishing expedition for the defense.
“The Court should not require the Government to disclose the manner in which it will attempt to prove the charges,” Halligan wrote.
The dispute sets the stage for a high-stakes legal fight that could determine whether Comey will stand trial.
Comey Used a Private Gmail Account While Criticizing Clinton for Similar Behavior
One of the most controversial revelations is that Comey — who publicly reprimanded Hillary Clinton in July 2016 for using a private email server as secretary of state — was simultaneously using a private, pseudonymous Gmail account to discuss sensitive FBI matters with Richman.
This detail, highlighted in the new DOJ documents, has fueled accusations of hypocrisy and double standards.
Publicly, Comey framed Clinton’s server as reckless.
Privately, he was doing something strikingly similar.
Prosecutors argue the Gmail communications show Comey was well aware of, and actively involved in, shaping media narratives during the 2016 election — the very issue he later denied before Congress.
Coordinating with Richman After the Clinton Letter Went Public
Another key DOJ claim is that Comey began coordinating with Richman immediately after his letter to Congress became public on October 28, 2016.
The DOJ filing states:
“Almost immediately after sending the letter… the defendant appears to have begun coordinating with Daniel Richman to respond to resulting media coverage.”
This contradicts Comey’s earlier assertion that he had no involvement in media strategy related to the investigation.
According to the DOJ, on the very same day Comey notified Congress, he was already:
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discussing news coverage
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analyzing political reactions
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planning responses
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coordinating messaging with Richman
These details could become central to the obstruction and false-statements charges.
A Director Navigating a Political Minefield
To understand the full gravity of the newly released emails, one must return to the intense political atmosphere of late 2016:
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The Clinton campaign was ahead in national polls.
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Trump was campaigning on “drain the swamp” messaging.
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Media scrutiny of Clinton’s emails remained fierce.
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FBI leadership faced internal pressure to act quickly.
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Agents disagreed internally about the timing and strategy.
Within this context, Comey’s message — “I hate having to do it” — reads not as a confession of wrongdoing but as the lament of a man who understood the political explosiveness of his actions.
Yet prosecutors argue that Comey’s behind-the-scenes behavior contradicts the neutral posture he presented publicly.
Comey’s defense counters that he was acting independently, trying to preserve the FBI’s integrity, and making decisions in a no-win situation.
Both narratives now collide in a court of law.
The Larger Political Implications
The newly disclosed records do not just revisit the past — they reopen questions that have haunted both parties for years:
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Did Comey’s letter cost Hillary Clinton the election?
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Was FBI leadership biased for or against either candidate?
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What did Comey know about media interactions, and when?
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Was the FBI neutral during the most heated election in modern U.S. history?
Democrats long argued that Comey torpedoed Clinton’s campaign by creating the appearance of fresh wrongdoing days before the vote.
Republicans argue the opposite — that Comey’s decision not to charge Clinton reflected political favoritism.
The new emails provide ammunition to both sides.
Where the Case Goes From Here
Judge decisions in the coming months will determine whether:
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the charges against Comey proceed to trial,
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the defense succeeds in narrowing the indictment, or
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the Justice Department is forced to reveal more of its evidence.
Legal analysts say the case could hinge on:
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the interpretation of Comey’s intent
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the definition of “authorization” in media contacts
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whether his Gmail communications constitute official acts
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the credibility of Richman as a cooperating witness
Meanwhile, the political world is watching closely.
Comey’s decisions shaped the final days of the 2016 election — and his prosecution could shape how Americans view the institutions behind those decisions.
Conclusion: A Historic Chapter Reopened
Nearly nine years after the election that shook modern American politics, James Comey is again at the center of a national debate — this time not as a FBI director but as a defendant fighting for his reputation.
The newly released emails show a man torn between duty and optics, law and politics, secrecy and transparency. They show internal conflict, strategic maneuvering, and the heavy weight of history pressing down on a federal director who expected a Clinton presidency but acted in ways that helped shape a Trump one.
Whether Comey’s actions were motivated by principle, fear of backlash, or political miscalculation will ultimately be decided not in public forums but in federal court.
But one thing is certain:
The story of the 2016 election is not finished — and James Comey, once again, is at the center of the storm.
Adrian Hawthorne is a celebrated author and dedicated archivist who finds inspiration in the hidden stories of the past. Educated at Oxford, he now works at the National Archives, where preserving history fuels his evocative writing. Balancing archival precision with creative storytelling, Adrian founded the Hawthorne Institute of Literary Arts to mentor emerging writers and honor the timeless art of narrative.