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Gray Day: My Undercover Mission to Expose America’s First Cyber Spy by Eric O’Neill is a non-fiction book following the author’s investigation into the FBI’s most damaging spy. Mr. O’Neill is a cybersecurity expert and a former FBI agent.

I have read many books about cybersecurity, and many books which spy Robert Hanssen (code name: Gray Day) is mentioned, but I never realized the two subject had anything to do with one another, until now. Gray Day: My Undercover Mission to Expose America’s First Cyber Spy by Eric O’Neill is a thrilling memoir about the author’s FBI assignment to “work” for Hanssen while secretly investigating whether he is a Soviet spy or not.

The author starts by introducing the reader to his world of shadows. As an FBI “ghost” he was an expert at surveillance while blending into the background, gathering information without notice. Real spy work some might say.

As a young agent, Mr. O’Neill was tasked at joining the new cybersecurity division that Mr. Hanssen was put in charge of. Unbeknownst to the spy, the author was there to gather information. Unbeknownst to the author, he was part of a much larger investigation into one of the most damaging spies the US has known. Unbeknownst to Hanssen, his who promotion was a simple ruse.

The author got to know the spy very well, the worked close on the same projects and in close proximity. As the sole employee of the new department, Mr. O’Neill got the brunt of Hanssen’s wrath, demeaning mannerisms, insulting style of leadership.
Quite honestly, even if Hanssen wasn’t a spy it would be difficult to find people who’d want to work with him or for him.

The book goes beyond a spy vs. spy case. The author tells about the heavy price that individuals and families pay while one of the partners works a hectic, stressful job that requires lying to everyone (co-workers and family).

Mr. O’Neill wrote a very personal book, which reads like fiction but is a cautionary tale. He tells us what it’s really like working in intelligence in a cohesive, well written memoir. I just wonder what he couldn’t tell us?

This was a fascinating look into the FBI and counter espionage about one of the most notorious moles in our nation's history. If you've seen the film "Breach" then this will feel like you've read this story before however career AFTER the breach is fresh and new. Who would be better at identifying security loopholes than a spy? The story of Robert Hanssen is intriguing and beguiling. It is astonishing that this could go undetected for so long and proves that the Russians were, are, and remain a threat to our democracy..

The story of the takedown of Robert Hanssen, arguably one of the worst spies the United States has every had. Hanssen, a FBI employee, sold out to the Russians, giving them some of our most highly classified secrets for over twenty years. He was responsible for many deaths, and did untold damage to our national security.
The author was a young FBI "ghost", a person assigned to surveillance of people. He found himself placed in a position to work closely with Hanssen, trying to gain his trust, all the while attempting to bring him to justice.
The story is gripping. You find yourself pulling for the author's success.
Here's hoping that the FBI, and other agencies, learned from their mistakes, and that they never have another traitor like Hanssen in their midst!

I assumed, after reading other accounts of Robert Hanssen's horrific "career" in espionage on behalf of the USSR and, later and more briefly, the Russian republic, that I was familiar with the outlines of the case, especially since I'd also seen the film "Breach", which features author Eric O'Neill as a key character. (Indeed, those who have seen and recall that film will find many parts of this book very familiar.) But there was plenty here to find intriguing, from O'Neill's background as a low-level FBI employee assigned to follow suspects for hours at a time, changing his look as frequently as needed to blend into the background and avoid detection, to O'Neill's assertion that Hanssen's crimes make him the first cyber-spy of the modern era.

Indeed, it's that dual structure -- O'Neill is simultaneously trying to recreate the tension of his experiences trying to cope with the volatile Hanssen and assist the mole hunt that uncovered him in its final weeks, while at the same time trying to educate the reader about cyber-espionage and laying the groundwork for his final argument -- that makes the book slightly less compelling than it could be. The author jumps back and forth between the attempt to take down Hanssen, and events before and after that mole hunt -- some directly relevant, but others, that occurred long after Hanssen had pled guilty and headed off to a lifetime behind bars, that felt like a reach. It's not that the argument about cyber-espionage as a significant threat, and O'Neill's argument that Hanssen was early to identify the weaknesses of the FBI's technology (and to exploit them, of course) is, eventually, compelling. But the constant shifting from one theme or idea or experience to another ultimately made this a book that was distracting to read. Just as I was becoming engaged, the author veered off on a new tangent -- also important, also interesting but nonetheless something that felt like a distraction.

The bottom line? Imperfectly structured, but nonetheless fascinating. In some ways, indeed, I found O'Neill's post-FBI career and current involvement in anti-cyber espionage more fresh and intriguing than the rehash of the Hanssen affair. I assume the latter is there because, hey, he's never been able to tell his own version of the story and he can relate it to his broader points, but the latter were really what I ended up finding the most fascinating. Where are our weaknesses today, and are we aware that they ARE weaknesses? I couldn't help feeling that however fascinating this book could become, there remained a lot left unanswered with respect to that crucial question, if not about Robert Hanssen.

I'd recommend this to anyone who isn't very familiar with the Hanssen case and who hasn't seen "Breach", in particular. The more you know, the more repetitive about half to two-thirds of this book will feel.