‘I hate having to do it’: The Comey ‘October Surprise’ in 2016 that was no surprise to some at FBI

Months before he was fired as FBI director, James Comey expressed discomfort in the final weeks of the 2016 election when he was compelled to tell Congress that agents had found more Hillary Clinton emails on a laptop belonging to disgraced former Democrat Congressman Anthony Weiner, according to newly released court records.

“I hate having to do it," Comey wrote a friend in an email recently made public by federal prosecutors that gives Americans new insights into the ex-director's mindset during the contentious 2016 presidential election.

Comey is currently being prosecuted on charges he misled and obstructed Congress when he denied authorizing leaks to the media about the FBI’s Clinton investigation in 2016.

As Comey denies wrongdoing and fights to dismiss the charges, the Justice Department has released never-before-seen messages from Comey to his friend and confidante Daniel Richman, showing that Comey expected Clinton to emerge victorious over Donald Trump and shining more light on the so-called “October Surprise” — the Weiner laptop emails — which actually came as no surprise to FBI leaders.

In fact, since-fired FBI special agent Peter Strzok had known about the Weiner laptop emails since September 2016, well before Comey's email to Richman.

Comey expected Clinton to be “president-elect Clinton” after the November 2016 election, according to recently-unearthed emails he sent to Richman, and further emails released this week by the DOJ show that he was unhappy but believed he needed to alert Congress to the fact that the bureau had found more Clinton emails on the Weiner laptop.

Richman, a former DOJ official and current Professor of Law at Columbia University Law School, was assisting the FBI during the 2016 election. It is already public knowledge that Richman later assisted Comey by leaking the so-called “Comey Memos” to the New York Times in 2017 after Comey's firing by President Donald Trump.

The DOJ alleges the emails show Comey was aware of and was encouraging Richman's contacts with the media in 2016, contrary to his later claims to Congress. Comey has pleaded innocent and portrayed his prosecution as a political vendetta.

Despite going after Clinton for her improper use of a private email server, Comey himself was using a personal and anonymous Gmail account to discuss FBI matters with Richman, the new memos show.

Comey did not respond to a request for comment sent to him through his lawyer Patrick Fitzgerald.

DOJ releases secret emails from October 2016 after Comey lawyer’s court request

Last month, Comey lawyer Jessica Carmichael told the federal court that her client “moves this Court to order the government to provide a bill of particulars as described below” as she argued that “Mr. Comey seeks specificity with respect to Counts One and Two of the indictment to apprise him of the offenses with which he is charged and to allow him to prepare a defense at trial. The indictment in its current form does neither.”

U.S. Attorney Lindsey Halligan filed her response this week, arguing that “contrary to defendant’s request, a bill of particulars is not to be utilized as a discovery device” and that “given that the indictment provides defendant with the essential facts constituting the offenses with which he is charged, the Court should not require the Government to disclose the manner in which it will attempt to prove the charges, the precise manner in which the Government intends to prove that the crimes charged were committed, or to provide the defendant a preview of the Government’s evidence or legal theories.”

The DOJ’s court filing also shed new light on Comey’s actions in October 2016, noting that the FBI director’s alleged scheming with Richman kicked into high gear after he sent Congress his October 2016 letter.

“Almost immediately after sending the above-described letter, the defendant appears to have begun coordinating with Daniel Richman … to respond to resulting media coverage,” the DOJ said. “On the same day that defendant sent his letter to Congress, he was already coordinating with Richman on the coverage.”

Richman has previously admitted to agents in interviews that he routinely communicated on behalf of Comey, his longtime friend, with New York Times reporter Michael Schmidt, whose work was among the newspaper's 2018 Pulitzer-winning stories on alleged Russian election interference. The goal, Richman told the FBI, was "to correct stories critical of Comey, the FBI and to shape future press coverage" outside the bureau's official press office, according to internal FBI memos.

"Richman was pretty sure he did not confirm the Classified Information. However, Richman told the interviewing agents he was sure 'with a discount' that he did not tell Schmidt about the Classified Information," one FBI memo recounted.

Defending Comey’s letter to Congress on Clinton

Comey largely exonerated Clinton in a July 2016 press conference, saying he would not seek criminal charges against her for the misuse of a personal email account to transmit classified information. His FBI then turned its focus to launching the Trump-Russia collusion-focused Crossfire Hurricane inquiry at the end of that same month.

Comey alerted Congress in October 2016 that further Clinton emails had been found on a laptop belonging to Weiner, then the husband of top Clinton aide Huma Abedin. The files were on Weiner's laptop in a folder labeled "Life Insurance."

Richman told Comey on Oct. 28, 2016 — the day that Comey sent his letter to Congress — that “Wittes and I are spending a lot of time saying your letter means exactly and only what it says. ‘Cause we, you know, speak English.”

“Wittes” is almost certainly a reference to Comey friend Benjamin Wittes, who had written an article for Lawfare that day titled, “Memo to the Press: What Comey's Letter Does and Doesn't Mean.”

“Comey represented to Congress that the Clinton email investigation was ‘complete.’ But as the letter relates, new emails have now come to the bureau's attention that appears relevant to the email investigation. (Weiner's estranged wife is one Clinton's top aides.) Comey has okayed a review of that new information to determine whether the emails contain classified material and also whether they are, in fact, relevant,” Wittes wrote at the time. “And this fact renders his prior statement to Congress no longer true. The key point here, in other words, is not that Comey is ‘reopening’ a closed matter because of some bombshell. It is that he is amending his public testimony to Congress that the FBI is done while the bureau examines new material that may or may not have implications for investigative conclusions previously reached.”

Wittes also offered up a defense of Comey in his October 2016 article, saying, “What you can't reasonably say is that Comey has been anyone's political lackey. Over the howling objections of many Republicans, he ended the Clinton email investigation, concluding that ‘no reasonable prosecutor’ would go forward with a case.

"Over the snarls of the Clinton forces, at the same time, he commented quite disparagingly about the behavior of the woman who is likely to become his boss. And now, with the election only days away, he has amended his prior resolution of the case to deal with new information. Say what you will about the FBI, but it's surely been independent," he said.

In his message back to Richman that day, Comey misspelled the names of all three main players in the laptop saga — wrongly spelling the names of Clinton, Weiner, and Abedin, but nothing else.

“You are both right. And he nailed the position I found myself in. The team comes to me yesterday and says there are over 600,000 emails on Weiser’s [sic] computer, and they include 10 years of Huma Abeddin’s [sic] emails with HRC and that metadata shows are from the ‘missing’ blackberry domain used for the first months of Secretary Clinin’s [sic] tenure at state,” Comey wrote in the newly-disclosed email. “Appears Huma didn’t know all her stuff was backing up to his computer. What am I gonna do? I gotta authorize the work and correct the record with congress. Imagine what I would have done to my institution if I didn’t do both of those things. Not a hard call although I hate having to do it.” 

Richman wrote to Comey the next day to “make sure you keep your eyes shut” because “the country can’t seem to handle your finding stuff,” 

Comey replied: “Thanks for the battling you have done against unreason. This is a strange time. B[u]t we press on.”

The next day, Richman sent Comey an email about an opinion piece he had been asked to write for the New York Times about Comey’s letter to Congress. Richman stated that he was “not inclined” to “write something” but that he would “do it” if Comey thought it would “help things to explain that [Comey] owed [C]ong[ress] absolute candor” and that Comey’s “credibility w[ith] [C]ong[ress] w[ould] be particularly important in the coming years of threatened [C]ong[ress] investigations.”

“No need. At this point it would [be] shouting into the wind,” Comey said in his Oct. 30, 2016 response back. "Some day they will figure it out. And as [Individual 1 and Individual 2] point out, my decision will be one a president-elect Clinton will be very grateful for (although that wasn’t why I did it).”

“When I read the times [New York Times] coverage involving [Reporter 1], I am left with the sense that they don’t understand the significance of my having spoke about the case in July [2016]. It changes the entire analysis. Perhaps you can make him smarter,” Comey told Richman on Nov. 1, 2016.

Richman responded the next day, saying: “This is precisely the case I made to them and thought they understood. I was quite wrong. Indeed I went further and said mindless allegiance to the policy (and recognition that more evidence could come in) would have counseled silence in july to let hrc [Hillary Clinton] twist in the wind.”

Richman soon added, “Just got the point home to [Reporter 1]. Probably was rougher than u would have been.”

Comey then emailed Richman shortly thereafter, saying “pretty good” and sending a link to a New York Times piece about Comey’s alleged options in late October 2016 concerning the Clinton email investigation. Comey told Richman, “Someone showed some logic. I would paint the cons more darkly but not bad.”

Richman then responded: “See I *can* teach.”

The DOJ said this week that “despite the defendant’s above-described November 2016 instruction to Richman — and his subsequent expression of approval regarding Richman’s provision of information to the media concerning the Clinton email investigation — the defendant” went on to allegedly mislead Congress in 2017 and 2020 when he denied authorizing Clinton-related media leaks in 2016.

Comey lets Clinton off the hook

Notes from a 2016 FBI interview with Abedin reveal Obama used a pseudonym when emailing Clinton in 2012. Obama later claimed in March 2015 that he found out about her private server “the same time everybody else learned it — through news reports.”

The FBI’s Clinton emails investigation — dubbed “MidYear Exam” — was led by FBI officials who would also soon be involved in the Trump-Russia Crossfire Hurricane investigation as well. Since-fired FBI agent Peter Strzok exchanged numerous anti-Trump texts with former FBI lawyer Lisa Page, with whom he was having an affair, and Strzok promised Page that “we’ll stop” Trump in August 2016.

Kevin Clinesmith, now an ex-FBI lawyer, expressed favor toward Clinton and said “Viva le resistance" in the weeks after Trump's win. Clinesmith later pleaded guilty in Special Counsel John Durham’s investigation for editing an email in 2017 to falsely state Trump campaign associate Carter Page was “not a source” for the CIA.

DOJ inspector general Michael Horowitz said that “we found that the inappropriate political messages cast a cloud over the MidYear investigation, sowed doubt about the credibility of the FBI’s handling of it, and impacted the reputation of the FBI” and that “we found the implication that senior FBI employees would be willing to take official action to impact a presidential candidate’s electoral prospects to be deeply troubling.”

The DOJ watchdog also noted “the preference for consent over compulsory process” to obtain evidence in the investigation, decisions not to seek certain evidence such as senior Clinton aides’ personal devices, “voluntary” witness interviews, “Queen for a Day” immunity agreements with witnesses, the use of “consent agreements” with Clinton’s lawyers, and Clinton’s lawyers being allowed in her July 2, 2016 interview, which “was inconsistent with typical investigative strategy.”

Without alerting then-Attorney General Loretta Lynch of what he would be saying, Comey announced in July 2016 that she was “extremely careless” in handling classified emails but that charges should not be filed against her.

Comey said that from the group of 30,000 Clinton emails returned to the State Department, 110 e-mails in 52 email chains were determined to contain classified information when sent, eight chains containing Top Secret information, 36 chains containing Secret information, and eight containing confidential information. He said 2,000 more emails were “up-classified” to make them confidential after they were sent.

Comey also claimed he “found no evidence that any of the additional work-related emails were intentionally deleted in an effort to conceal them.”

Horowitz said in 2018 that, at key moments such as the July 2016 speech, Comey “clearly departed from FBI and Department norms, and his decisions negatively impacted the perception of the FBI and the Department as fair administrators of justice.”

Clinton was investigated under 18 U.S.C. 793(f), whose statute cites “gross negligence.” Comey said in July 2016 that “although we did not find clear evidence” that Clinton or her associates “intended to violate laws governing the handling of classified information, there is evidence that they were extremely careless in their handling of very sensitive, highly classified information.”

An earlier draft of the FBI statement said “there is evidence to support a conclusion that Secretary Clinton, and others, used the private email server in a manner that was grossly negligent with respect to the handling of classified material.”

Comey declared that “although there is evidence of potential violations of the statutes regarding the handling of classified information, our judgment is that no reasonable prosecutor would bring such a case.”

Horowitz’s 2018 report concluded Comey’s actions were “extraordinary and insubordinate” when he announced Clinton wouldn’t be charged.

Unpacking the “October Surprise”

The FBI’s Clinton emails investigation was forced back into public view when, in late September 2016, thousands of emails belonging to Abedin were found on the laptop belonging to her then-husband, Weiner. Comey sent a letter to Congress on Oct. 28, 2016, saying the FBI uncovered emails possibly pertinent to the investigation.

"In connection with an unrelated case, the FBI has learned of the existence of emails that appear to be pertinent to the investigation,” Comey wrote in his letter. “I am writing to inform you that the investigative team briefed me on this yesterday, and I agreed that the FBI should take appropriate investigative steps designed to allow investigators to review these emails to determine whether they contain classified information, as well as to assess their importance to our investigation."

FBI agent John Robertson, who worked in its New York office’s child sex crimes unit and was later cited (though not named) in Horowitz’s 2018 report on the handling of the investigation of Clinton’s unauthorized private email server, was quoted in the book October Surprise.

Robertson unearthed tens of thousands of Clinton emails in late September 2016 on the laptop belonging to Weiner, the husband of Clinton aide Huma Abedin, in a sex crimes case involving underage girls, but for weeks after being alerted, top FBI leaders (including Strzok, since-fired FBI Deputy Director Andrew McCabe, and former FBI counterintelligence chief Bill Priestap) took little to no action to investigate.

“The crickets I was hearing was really making me uncomfortable because something was going to come down,” Robertson reportedly later told Justice Department investigators. “Why isn’t anybody here? Like, if I’m the supervisor of any [counterintelligence] squad … and I hear about this, I’m getting on with headquarters and saying, ‘Hey, some agent working child porn here may have [Hillary Clinton] emails. Get your ass on the phone, call [the case agent], and get a copy of that drive,’ because that’s how it should be. And that nobody reached out to me within, like, that night, I still to this day don’t understand what the hell went wrong.”

Robertson reportedly wrote a “Letter to Self” in late October after an Oct. 19, 2016 meeting, during which he implored then-Assistant U.S. Attorney Amanda Kramer of the Southern District of New York to push FBI leadership to look at the thousands of emails he had unearthed.

“I have very deep misgivings about the institutional response of the FBI to the congressional investigation into the Hillary Clinton email matter. … Put simply: I don’t believe the handling of the material I have by the FBI is ethically or morally right. But my lawyer’s advice — that I simply put my SSA on notice should cover me — is that I have completed CYA [Cover Your Ass], and I have done so,” Robertson wrote. “Further, I was told by [Kramer] that should I ‘whistleblow,’ I will be prosecuted.”

Robertson continued: “I possess — the FBI possesses — 20 times more emails than Comey testified to. … While Comey did not know at the time about what I have, people in the FBI do now, and as far as I know, we are being silent. … If I say or do nothing more, I am falling short ethically and morally. And later, I may be accused of being a Hillary Clinton hack because of the timing of all this. … But if I say something (i.e., whistleblow), I will lose my reputation, my career, and risk prosecution. I will also be accused of being a Donald Trump hack.”

The FBI agent wrote that “nothing could be further from the truth” because “I am apolitical.”

Horowitz’s 2018 report noted a federal search warrant was obtained on Sept. 26, 2016, for Weiner’s devices and that the “Weiner case agent” (Robertson) noticed “within hours” that there were “over 300,000 emails on the laptop,” including between Clinton and Abedin. The FBI New York Field Office’s William Sweeney was reportedly alerted two days later, and key FBI executives such as McCabe were informed by Sweeney.

Text messages show McCabe, Strzok, and Priestap discussed the Weiner laptop on Sept. 28, 2016, and Strzok said he initially planned to send a team to New York to review the emails, but a call with the FBI’s New York office was scheduled for the next day instead. Horowitz wrote that “after October 4, we found no evidence that anyone associated with the MidYear investigation, including the entire leadership team at FBI Headquarters, took any action on the Weiner laptop issue until the week of October 24, and then did so only after the Weiner case agent expressed concerns to SDNY, prompting SDNY to contact the Office of the Deputy Attorney General on October 21 to raise concerns.”

Horowitz said that the FBI’s explanations were “unpersuasive justifications for not acting sooner” and “the fact that Strzok and several other FBI members of the MidYear team had been assigned to the Russia investigation … was not an excuse for failing to take any action.”

The public version of the 2018 report by the DOJ watchdog also uncovered evidence that the FBI had delayed following up on information about Clinton emails found on a laptop belonging to Weiner and that the delay may have come from the FBI’s desire to emphasize the baseless Trump-Russia collusion investigation over the Clinton emails scandal.

Horowitz wrote, "We did not have confidence that Strzok’s decision to prioritize the Russia investigation over following up on the MidYear-related investigative lead discovered on the Weiner laptop was free from bias.”

Horowitz found that it was not until Oct. 27, 2016 “when Comey was briefed by the FBI Clinton email investigation team regarding the Weiner laptop issue” despite the Clinton emails being discovered on the Weiner laptop weeks before. Comey’s communications with Richman about his letter to Congress — released by the DOJ in recent days — began the next day.

“In assessing the decision to prioritize the Russia investigation over following up on the MidYear-related investigative lead discovered on the Weiner laptop, we were particularly concerned about text messages sent by Strzok and Page that potentially indicated or created the appearance that investigative decisions they made were impacted by bias,” Horowitz wrote, adding that “we did not have confidence that Strzok’s decision to prioritize the Russia investigation over following up on the MidYear-related investigative lead discovered on the Weiner laptop was free from bias.”

Strzok later admitted in a book that he absolutely prioritized the Trump-Russia investigation over the one into Clinton.

“There was simply no equivalence between MidYear and Crossfire,” Strzok claimed in his book, Compromised, referring to the Clinton emails investigation and the Trump-Russia investigation. “At its core, MidYear was a glorified (because it involved Hillary Clinton) mishandling case, the type that but for the celebrity subject rolls through WFO on a weekly basis. Crossfire was a first-of-its-kind, enormous investigation into complex, ongoing attacks on our presidential elections and Russian interactions with members of one of the candidate’s campaigns. Of course, I had prioritized that.”

Horowitz wrote that “the FBI’s inaction had potentially far-reaching consequences” because Comey told Horowitz that “had he known about the laptop in the beginning of October and thought the email review could have been completed before the election, it may have affected his decision to notify Congress.” Comey told Horowitz, “I don’t know [if] it would have put us in a different place, but I would have wanted to have the opportunity.”

Comey sent a follow-up letter on Nov. 6, 2016 telling Congress that “we have not changed our conclusions” about not charging Clinton.

Trump defeated Clinton 304-227 in the Electoral College two days later.

Clinton blames Comey for her loss

The FBI investigation was closed again just before the election. Former President Barack Obama and Clinton both criticized Comey’s reopening of the investigation, with Clinton eventually blaming Comey for her loss.

Clinton wrote in her 2016 memoir, What Happened, about what she dubbed “The Comey Effect” as she argued, “What happened in the homestretch that caused so many voters to turn away from me? First, and most importantly, there was the unprecedented intervention by then FBI Director James Comey.”

Abedin wrote in her own book, Both/And, that Comey’s “decision to play God” is why Trump won and claimed that “the totally gratuitous reopening of the FBI email investigation had tilted the election” in Trump’s favor.

The delays by Strzok and other FBI leaders — knowing about the Weiner laptop emails in September 2016 but failing to act until pressure stemming from Robertson in late October 2016 — are not mentioned in Clinton’s book nor in the one penned by Abedin.

Comey is now slated to go on trial in the Eastern District of Virginia in January 2025 on charges stemming from allegedly misleading about authorizing Clinton-related leaks in October 2016.

The Comey trial may end up being just one part of the Trump DOJ’s “grand conspiracy” investigation related to Russiagate and other aspects of anti-Trump lawfare, and subpoenas are being sent out from the nation’s capital and from Florida as a clearer picture about Comey’s actions in 2016 continues to emerge.