Excerpt

Inside James Comey’s Bizarre $7M Job as a Top Hedge Fund’s In-House Inquisitor

A few years before his unforgettable cameo in the 2016 presidential election, the future FBI director worked at Ray Dalio’s Bridgewater Associates, where he pursued the firm’s goal of “radical transparency” with prosecutorial zeal.
Inside James Comeys Bizarre 7M Job as a Top Hedge Funds InHouse Inquisitor
Illustration by Khoa Tran.

They called him the “Godfather.”

Before he was FBI director, Jim Comey was general counsel of Bridgewater Associates, the world’s largest hedge fund. There he would practice and perfect the knack for drama that later thrust him into the center of the national political scene.

Comey was far from a household name when he joined Bridgewater in 2010. He was best known for his stint as US attorney for the Southern District of New York, and he made no secret to friends of his financial motive for jumping to Bridgewater, which would pay him $7 million per year.

Bridgewater founder Ray Dalio, famed for devising a collection of so-called “Principles,” also made no secret of his hopes for the new hire. Dalio’s Principles, later adapted into a best-selling book and TED Talks, centered on a philosophy of “radical transparency” that involved tearing into the firm’s troublesome corners. They called for videotaped, internal “trials,” and investigations of even the smallest problems at the firm; these were often called “diagnoses” to find the “root cause.” Staff voted in real-time on disagreements. Dalio told staff that Comey would be like a godfather adjudicating it all.

Comey’s early days were inglorious. He often acted as if the hedge fund’s rules did not apply to him. Most every meeting, no matter how minor, was recorded at Bridgewater’s Connecticut headquarters, and at six foot, eight inches, Comey would sometimes reach toward the ceiling to deactivate any hidden recording devices in the light fixtures. He tended to speak in meetings from his experience, so Dalio would quickly correct him that he should apply the firm’s Principles rather than his own (one read, “Don’t tolerate badness,” while another prescribed “truth at all costs”).

Comey was smart enough to course correct—he was soon citing Principles with such frequency that Dalio told the whole firm that his new general counsel was a “chirper,” or someone who repeats stale ideas. Evidently eager to finally prove his worth, Comey found an opportunity to earn some points.

A relatively new lawyer on Bridgewater’s staff, Leah Guggenheimer, had taken to The Principles with gusto. She ostensibly worked in the operational side of the organization, but had earned a reputation for hunting firmwide for “badness,” including writing up a colleague for failing to bring in bagels on the agreed-upon day. This went on long enough that her colleagues voted to let her go. Her salary was cut off.

Dalio caught wind and didn’t like the idea of penalizing an employee—even a tedious one—for speaking her mind. He called in Comey for a second opinion.

Comey seemed to sense an opening to impress his new boss.

“Do you want it done like case law?”

Dalio energetically confirmed that he did.

“Well, Ray, the trial has happened. It’s gone through due process. It looks like it followed The Principles. So reopening it doesn’t make any sense, unless we hear it de novo.”

“What’s that?”

“You assume that the other trial never happened and you look at everything fresh.”

Dalio was fine with that.

Comey threw himself into the investigation. He listened to reams of meeting recordings and told Dalio that his review indicated the firing was justified.

Dalio concluded that beyond adjudicating the blow by blow of the bagels, Comey had performed a poor diagnosis:

“You didn’t get to the root cause.”

Dalio ordered a third investigation.

This time around, Comey applied brute force. He searched the records of Guggenheimer’s company-issued cell phone and found that she’d turned it on at home after her trial. When she protested that she needed to save personal contact information, Comey said she should have asked for permission.

He also began searching through the files on Guggenheimer’s office computer. Amid the usual mundanity, Comey came upon what he thought was quite the kompromat. Guggenheimer, a single woman, was using the computer to send messages on dating websites. Some of the messages bordered on blue—“near pornographic,” Comey told some at Bridgewater.

Dalio saw it differently. “What is pornography?” he mused. People have their private business, and the messages weren’t nearly a fireable offense, he concluded.

“Weak case, Jim,” Dalio told him.

Embarrassed in more ways than one, Guggenheimer decided not to return.

Comey’s responsibilities included oversight of Bridgewater security. This vast role gave him an excuse to poke and prod in virtually all corners of the firm. As one Principle laid out, “You should have such good controls that you are not exposed to the dishonesty of others.”

The taping of meetings represented just the tip of the surveillance ecosystem at Bridgewater. A slew of ex FBI agents staffed the security team. Not only did cameras cover seemingly every inch of the property, but they seemed to be watched in real time. Staffers who left their desks even briefly would return to sticky notes left on their computer monitors admonishing them for failing to put up a screen saver. New employees were often warned to be careful about their use of the company gym, which lent out clothes. One staffer, exhausted after a particularly tough workout, was chastised after absentmindedly walking out wearing a pair of Bridgewater loaner socks. The employee was let go. (A spokesperson for Dalio said, “No one was ever fired for taking a pair of socks.”)

As Comey’s search for office bugs indicated, most Bridgewater employees had a quite reasonable fear of being listened in on. When personal calls had to be placed during company time, many trudged out of the office and into the surrounding woods. That lasted roughly until a rumor circulated inside the fund that Comey’s team was studying how to install devices in the trees that could intercept phone calls before they reached surrounding cell phone towers. (A spokesperson for Dalio said Comey did not investigate installing devices in trees. Comey declined to be interviewed; he wrote in an email, “I will buy the book when it comes out.”)

As head of security, Comey reported to Dalio’s longtime deputy Greg Jensen, who seemed eager to prove that he took the protection of Bridgewater’s secrets as seriously as Dalio. With little evidence of actual offending behavior to snuff out, they created their own. Comey helped come up with a plan to leave a binder, clearly labeled as Jensen’s, unattended in the Bridgewater offices. It worked like a charm. Comey watched as a low-ranked Bridgewater employee stumbled upon the binder and began to peruse it. Jensen and Comey put the employee on trial, found him guilty, and fired him, with Dalio’s approval.

During and after Comey’s era at Bridgewater, tens of thousands of hours of the firm’s internal deliberations, arguments and trials were uploaded into what was called the “Transparency Library” and available for playback for all at the firm.

Lordy, there was plenty to watch.

No doubt Comey’s most infamous internal case was his prosecution of Bridgewater co-chief executive officer, Eileen Murray, who stood out like a pimple in Bridgewater’s blue-blooded executive suite. She’d grown up in a housing project in Queens, rarely wore skirts, never married, never had children, and talked frequently about her dogs. A former Morgan Stanley executive, she sent emails off the cuff, all lowercase, with typos, suggesting she was too busy to give anything her full attention.

The proximate cause of Murray’s lesson in the application of The Principles was innocuous enough. A job candidate mentioned to a Bridgewater executive that he was familiar with the hedge fund’s head of accounting, Perry Poulos, one of Murray’s hires. The job candidate evinced surprise—didn’t they know Poulos had been fired from Morgan Stanley?

Comey grabbed a former FBI agent on the Bridgewater staff and went to intercept the unsuspecting Poulos. The duo pulled him into a conference room without warning.

“Hi, guys,” Poulos said.

“We just want to know, is there anything in your background we should know about?” Comey responded.

“I had some things there, but it’s all cleared up now.”

“You wouldn’t mind if we ask a few questions and look a little more?”

There’s really nothing to find, Poulos said. Go ahead.

He exited the room, heart racing, and soon found Murray. She knew, as he did, that he had been let go from Morgan Stanley after questions were raised about his expenses. But Murray sensed a larger target at play. “It’s not you,” she told Poulos. “It’s me. They are trying to get to me.”

Comey called in Poulos for another interview.

“Did you talk to anyone about this?” Comey asked.

“No.”

“Are you sure?”

“No, I haven’t talked to anyone.”

“You live with Eileen, don’t you?”

Knowing Bridgewater’s reputation for intimate relationships, Poulos assumed Comey was sniffing for a romantic angle. During the week, Poulos said, he sometimes spent the evening at Murray’s place, in separate bedrooms.

“Even that evening, after we spoke, you didn’t talk to her?” Comey asked.

“I don’t remember saying anything in particular.”

The answer evidently didn’t strike Comey as credible, so the same question was asked of Eileen. Did she speak to Poulos? She answered no. Murray was instructed to write a memo with everything she knew about Poulos’s background.

The email that landed in Comey’s inbox, labeled as sent from Murray’s BlackBerry, was pristine. The grammar was clean and every word was properly capitalized. Comey showed it to Jensen. Both agreed it could not possibly have been written by her. Comey had access to security cameras. He pulled the footage and showed it to Jensen. Murray, sitting at her desk, was on camera, clearly in conversation with a subordinate in the minutes leading up to the email’s being sent. One could even pinpoint the moment she asked her subordinate to hit send.

Comey and Jensen pulled Murray into another meeting.

Are you sure you didn’t talk to anyone about this? they asked.

“Of course not.”

Even as the words left her mouth, Murray must have known she had made a mistake. She had worked on the email with an assistant, dictating phrases and going back and forth until they had come up with clean answers. She had been visibly nervous that she was walking into a trap and wanted to get it all exactly right. But now she was in a deeper hole of her own making. She had now been dishonest twice—once about speaking to Poulos, and now about typing the email.

Murray fled to Dalio and confessed her sins. She had lied only out of panic. She hadn’t been feeling herself, she said. She had just been trying to stay out of Comey’s crosshairs, and to keep Poulos away from the dragnet, too. “It was a white lie,” she said.

Dalio paused to confirm that the tape recorder was on and then said that Bridgewater was a place where liars were punished. There would have to be a trial.

It wasn’t just a trial, it was the trial. The investigation of Murray and Poulos went on for nine months. Cameras rolled all the while as Comey and Jensen probed Murray and Poulos on their transgressions. Everyone at the firm saw footage of Murray sitting at her desk, dictating the infamous email. The inquest didn’t stop at Murray’s pair of confessed lies. Comey seemed to act as if he had gotten Al Capone on tax evasion—once Comey had her in court, he had an excuse to investigate her whole life’s story.

Murray walked past Comey’s office one day to see the walls covered in newspaper clippings, and sticky notes, all about her, with lines drawn all over like a police sketch board on a procedural television series. She felt sick to her stomach.

It seemed to Murray and those sympathetic to her as if Dalio couldn’t get enough. He sat in as judge and turned the investigation into a real-time case, called “Eileen Lies.” Videos were released weekly, as serialized viewing for all Bridgewater staff. The updates were a combination of reality television, soap opera, and cinema verité. Comey played bad cop; in one video, he told Poulos, “Just tell the truth, it might make you feel good.” Jensen cast himself as the victim. “You lied to me,” he told Murray.

New episodes of “Eileen Lies” continued to air even after Poulos was fired, and after Murray’s assistant—called to testify against her boss—decided to resign instead.

After the better part of a year, even Comey and Jensen could wring no more juice out of the incident. Jensen presented his final argument: Eileen was an inveterate liar, and an avowed violator of the most sacred of The Principles. She had to be fired, for the good of the firm. Comey backed him up.

Dalio punted. Murray had lied, he ruled, but she hadn’t been proven to be a liar. The whole incident, Dalio told the firm, was a learning experience. It inspired him to write two new Principles. One dealt with white lies—they were acceptable, in small quantities. The other new Principle: “Everything looks bigger up close.” Of course, Murray would have to pay penance. He stripped her of her co-CEO title, bouncing her down to firm president. Everyone was unsatisfied. Murray had lost her role and her dignity. Comey was even more apoplectic—he had proven his case and lost anyway

In time, Comey came to see that a job at the world’s biggest hedge fund was not the slam dunk it had once seemed. Comey’s name was being whispered about for high-level government jobs, and what was happening at Bridgewater had the potential to burn, rather than burnish, his résumé.

For all Bridgewater’s talk of radical transparency, considerable secrecy surrounded Comey’s own resignation in October 2012, which came without an immediate explanation from Dalio. Questions piled up, and when employees were asked to vote at a Bridgewater town hall on queries to be answered, the top-voted topic was Comey’s imminent departure.

Comey laid out his thinking in an email:

From: Jim Comey 
Sent: Wednesday, October 03, 2012 
To: Bridgewater 
Subject: Why is Jim leaving?

... I like Bridgewater very much. I love the idea of our culture of transparency and truth and find both addictive...

Like all of you, I have strengths and weaknesses. Among my strengths are some leadership abilities that are not critical here, but that are both needed and highly effective in the rest of the world… Those competencies are also what makes work and life fun for me….

... There is something in the logic-based, relentless pursuit of excellence that is inconsistent with the kind of joy that animates me… I’m not saying Bridgewater’s personality should be different; only that it is different. Bridgewater reflects Ray’s personality, which is a cool thing. But he and I are very different people. . . .

I will be better as a public sector leader and teacher for having been here.


From THE FUND: Ray Dalio, Bridgewater Associates, and the Unraveling of a Wall Street Legend by Rob Copeland. Copyright © 2023 by the author and reprinted by permission of St. Martin’s Publishing Group.