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Not a Good Day to Die: The Untold Story of Operation Anaconda

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At dawn on March 2, 2002, the first major battle of the 21st Century began. Over 200 soldiers of the 101st Airborne and 10th Mountain Divisions flew into Afghanistan's Shahikot valley - and into the mouth of a buzz-saw. They were about to pay a bloody price for strategic, higher-level miscalculations that underestimated the enemy's strength and willingness to fight.

After the attacks of September 11, 2001, Coalition forces quickly toppled the Taliban regime from the seat of government. But, believing the war to be all but over, the Pentagon and US Central Command refused to commit the forces required to achieve total victory in Afghanistan. Instead, they delegated responsibility for fighting the war's biggest battle to a tangle of untested units thrown together at the last moment.

Then the world watched as Anaconda seemed to unravel.

Denied the extra infantry, artillery and close air support with which they trained to go to war, the soldiers of this airborne assault fought for survival in brutal high-altitude combat. Backed up by a small, but crucial, team of special forces, they were all that stood between the Coalition and a military disaster.

Hardcover

First published March 1, 2005

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About the author

Sean Naylor

5 books82 followers
Sean D. Naylor, 48, is the author of Relentless Strike: The Secret History of Joint Special Operations Command, to be published in September 2015 by St. Martin’s Press. Since January 2015, he has been the intelligence and counterterrorism correspondent for Foreign Policy magazine. He previously spent 23 years as a senior writer for Army Times, where his principal beat for the last decade of his tenure was special operations forces. Prior to that, he covered combat operations, exercises, training, readiness, weapons systems, force modernization and the Army's senior leadership.
Mr. Naylor received his bachelor's degree in journalism from Boston University in 1988 and a Master of Arts in International Relations from the same institution in 1990. In 1987 he traveled to Pakistan and Afghanistan as a freelance reporter covering the Afghan mujahideen, meeting and conversing with Jalaluddin Haqqani, Gulbuddin Hekmatyar and Hamid Karzai, among others.
For Army Times, Mr. Naylor covered military operations as an embedded reporter in Somalia, Haiti, Bosnia, Albania, Macedonia, Kosovo, Afghanistan and Iraq.
His coverage of 2002’s Operation Anaconda in Afghanistan earned him the White House Correspondents Association’s 2003 Edgar A. Poe award for excellence in reporting an issue of regional or national importance. It also led to a best-selling book, Not A Good Day To Die: The Untold Story of Operation Anaconda, published in March 2005 by Berkley Books, New York, N.Y. Mr. Naylor is also the co-author, with Tom Donnelly, of Clash of Chariots – The Great Tank Battles, published by Berkley to favorable reviews in 1996.
Born in Canada, and raised in England and Ireland, Mr. Naylor became a U.S. citizen on March 14, 2000. He lives in Washington D.C. on Capitol Hill, reluctantly hung up his rugby boots 14 years ago after a 25-year playing career, and is an avid soccer fan.

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Displaying 1 - 30 of 156 reviews
Profile Image for Steve.
897 reviews274 followers
January 13, 2012
Too many Chiefs...

And definitely, due to micro-management of the battlefield, not enough of our Indians. Not a Good Day to Die, by Sean Naylor, is just a terrific battle-book. It's almost overwhelming in detail, but Naylor is a fine writer taking you, with effective prose, to the mountains of Afghanistan. You as a reader are there as an Al Queda warrior studies mysterious ATV tracks in the mud while nearby he's being marked by a special ops sniper. You are there on the slopes as a few brave guys, struggling for air in the high altitude, battle an Al Queda bunker complex.

The battle itself was a mess, highlighting all the problems, a lot of them self-inflected, on the modern battle-field. The plan for Anaconda was suspect anyway, with its reliance (due to politics) on Afghan fighters driving, at night with no headlights, down a bad road into enemy country. To some extent Naylor soft-peddles this. But as events turned out this was not an operation killer, as terrific recon work had our forces holding the high ground, while our troops in the Shahikot valley occupied static (but hot) positions. With air strikes taking a toll, the killing time for Al Queda had begun. But military technocrats a thousand miles away (Air Force General Gregory Trebon in particular) wanted a piece of the action. As a result, Americans died due to a series of bone-headed decisions by Trebon and his on the ground man, SEAL Vic Hyder. Don't get me wrong, Anaconda was a "victory," but it could of been more. What is amazing is how Naylor is able to plot all of this, the various calls from troops on the ground and in the air, wrong transmissions, screw-ups, heroism, virtually every moment of the battle is there for the reader. What cuts against the effectiveness however is the dizzying use of acronyms - without a good glossary, and what seems to be an incomplete index. For example, the above General Trebon is last referenced on page 94, even though his (notorious) role goes on pretty much until the end of this 377 page book. And after checking out the paperback version, I saw this has still not been corrected. One other caveat, Naylor really seems to have something against the SEALS, who come across as whiney cowboy prima donnas. I'm not sure I buy that, it just comes across as something personal and beyond the lines of the story. Finally, as much as you come away disliking Hyder and Trebon's roles in all of this, their silence in this account leaves you feeling you've not yet heard the full story - though as it stands now, the indictment is formidable.

Profile Image for Sleepy Boy.
1,005 reviews
May 20, 2011
A sobering look at a completely mismanaged operation in Afghanistan. A true story of heroism, idiotic government bumbling, and how the men on the ground are the ones who have to deal with it and overcome the obstacles of not only the enemy but their faulty high command. Those responsible for this failed endeavor should be put before a court martial for their decisions and ignoring the intel presented to them by men who were actually on the ground. Their refusing to believe the facts cost us dearly in American lives. This story wouldnt be out of place in the Vietnam era when it comes to just how much intel was ignored and deemed irrelevant by people thousands of miles away from those who had boots and eyes on the ground. Overall an excellent book but one that just makes you shake your head and truly feel sorry for the men who had to endure what they did and the families who lost who they did.
Profile Image for Mike.
1,233 reviews173 followers
January 18, 2012
Not a Good Day to Die is a decent 3-Star account of our first major battle in Afghanistan after we kicked out the Taliban. This operation defines the acronym FUBAR. I decided the author wanted to get that concept across by writing almost 200 pages about the lead up and planning in such a way as to completely confuse the reader. I did not find his account of the plan (or lack of one) as enlightening or analytical as it should have been. I also did not enjoy the obvious slant he brought to the account, using anonymous sources and loaded descriptions to place blame. Not to say his portrayal wasn’t accurate but I felt he should have been more dispassionate in assessing responsibility. He is a reporter, not a trigger puller or commander in the fight (although he was there in theater). Once the battle gets going, you can’t help but hear the Jaws theme in the background as things go wrong. The intel assessment of how many Al Queda and other terrorist fighters proves to be wrong. The fighters stay and fight instead of fleeing from the US forces. The final chapter of the story is about the fight on Robert’s Ridge, where the Navy SEAL fell out of the chopper and the rescue team was shot down when trying to get into to find him. There were a lot of tough fights and brave men out there. His combat scenes are the highlight of the book. This operation ended and touched off a major pissing contest between various services and headquarters. It was FUBAR but the soldiers and airmen tasked with executing the fight performed magnificently. A good read (but what a terrible title for the book)
Profile Image for Jared.
18 reviews
September 10, 2011
I was part of this mission back in 2002 and I was initially excited when I heard that a book about Anaconda was being released. This narrative explains little to those who are familiar with operation and glorifies certain personalities (whom I know personally) that do not necessarily earn the laurels Naylor gives them here. Ultimately this book fails to deliver a definitive account of the planning or execution of Operation Anaconda, and the details which the author chooses to focus on are certainly not ones that I would have selected, nor do they contribute to the history which he is attempting to document. Still, at least a book was written about a military operation which is very personal to me.
Profile Image for Chris.
64 reviews28 followers
November 28, 2011
This was a great book detailing Operation Anaconda. It's apparent the author did a lot of research, and interview quotes from the people involved are seamlessly integrated throughout the text. The book is incredibly thorough, describing how everything ended up the way it did and why. The author seemed to give a very objective assessment about the successes, failures, and the men involved which I appreciated. Furthermore, this book did an excellent job showing how this operation exemplifies how the friction and fog of war can affect an operation and the troops involved.

Despite all of these favorable points, I will say there were times when I got lost as to the orientation on the battlefield when the author was covering specific troop placements. Sometimes the author would state a cardinal direction, and I'd be completely thrown off because I'd be thinking it was a completely different direction. A few maps were placed throughout the text, but I would have preferred more maps showing exactly where the troops were located incorporated, along the lines of the maps in the book We Were Soldiers Once...and Young: Ia Drang - the Battle That Changed the War in Vietnam.
Profile Image for Naim Luqman.
19 reviews2 followers
April 21, 2023
Sean Naylor has ways with word to make this chaotic operation grounded. Great explanation of why putting all your special forces into one giant basket doesn't necessary work.
Profile Image for Kevin.
218 reviews2 followers
September 13, 2010
One of the best "War books" I have read. The first half of the book did proceed relatively slow, laying all of the background for what would happen. However, it introduces all the main characters and paints a wonderful picture about what will take place during "Operation Anaconda."
Spoiler alert!: Operation Anaconda was the first battle with 'conventional' forces (i.e. rangers, mountain infantry, etc., not the special forces and delta working with the native tribal warlords like some of you might have seen on the tv)Initially, Anaconda started out as a decent plan to oust Al Qaeda from the Shahikot valley. Unfortunately, due to military leaders trying to govern the battlefield from too great distances, limiting what forces (artillery, helicopters, support trops, etc) were 'allowed' to enter afghanistan, disunity of command, ego, misunderstanding of capabilities, misunderstanding of the state of the battlefield, and false promises, alot of good guys died for no reason. I could write pages on what people did wrong, but you can find that out for yourself. Bottom line is: Don't place an air force general in charge of ground force operations, and lastly fight how you train. That is to say, if you train using artillery and air assets as support, then don't go to battle with any less, despite what General Franks or 'Donny' Rumsfeld says. You are bound for heartache.
Once the battle began it was quick paced and I couldn't put the book down. The author is not in the military, but was present at the briefings and during the battle. He has done his homework and has done a spendid job putting the details together in a concise way. From what I understand, he took some flak from higher military and defense, because of the bad light that it painted regarding their policy and performance.
Profile Image for Oceana2602.
554 reviews155 followers
March 13, 2011
Sean Naylor has an amazing talent for describing details.

I now know the personality of each of the 1700 US troops involved in Operation Anaconda, when they first met each other, and what their first dogs were called. Also, what they had for breakfast. On every single day of the mission. Well, I suppose there were some days they didn't have breakfast.

Sadly, Naylor does not have the same talent for storytelling, and so I know almost nothing about Operation Anaconda, because that information was kind of hard to make out between all the breakfast and dog-name details. Or maybe it has to do with the fact that I gave up "reading" this book after about 75 pages, then tried to skip through to the real information for the next 200 pages and finally jumped to the end, in the desperate hope that this would enlighten me, at last.

It didn't.

So, as far as battle accounts or reports about military operations go, this book is a complete failure.

I do feel strangely obliged to keep it on my shelf, though, for reference. I mean, who knows if the knowledge when First Sergeant Something or Lt.Col. Something else first served together and what were wearing when they did then may not be useful some day.

(also, if anyone knows any good books about Operation Anaconda, please tell me)

Profile Image for Evan.
784 reviews14 followers
February 16, 2020
I finished "Alone at Dawn" a few weeks ago and read this to find out more about the operation where John Chapman died. The book is fairly exhaustive, I think, with respect to the planning the lead up to the operation and what happened in the first few days. Unfortunately, I thought the writing was horrible - sentences were repeatedly 40 words or more and lots of passive voice (e.g., "Training their polyglot Afghan force in basic infantry tactics was no small task for, oddly enough, given the mission the Americans would ask them to perform a few weeks later, one field in which Zia and his small band of peasant warriors—only half the size of a U.S. infantry company when he joined forces with Texas 14—had almost no experience was combat."). I had to read sentences two or three times and sometimes still couldn't figure out what phrases were describing what.

Some of my thoughts
- Leadership, DefSec Rumsfield, did not want conventional troops in Afghanistan to avoid the drawn out operations American forces were doing in Bosnia.
- Before Anaconda, relying on Afghan militias, resulted in many Al Qaida troops escaping into Pakistan during the battle of Tora Bora. The same thing happened again at Shahikot.
- Naylor makes it sound like the military has hidden special forces that the public knows nothing about - not even the names.
- A multitude of reasons that Anaconda went horrible: no unity of command (each component, such as special forces, rangers, air force support, reported to their own leadership), breaking up units that trained together, not allowing infantry to bring their artillery support, none changing the plan when new intelligence revealed the original plan wouldn't work, and taking command away from the most qualified person to have it (Blaber)
- Amercian Special Forces are freaking amazing - well some of them. Some did their jobs and others were portrayed as whiners

Quotes I highlighted:
- "a lone AK-47-wielding guerrilla firing a bullet that cost pennies had come within millimeters of downing a multimillion-dollar Black Hawk helicopter and consigning the brigade commander, his air mission commander, operations officer, and air liaison officer, as well as an RTO and the air crew, to their doom."
- "By seizing the low ground, TF Rakkasan had put itself on terrain from which it was hard to identify the enemy positions from which it was receiving fire."
- "As ever in combat, it was left to captains and sergeants to bear the consequences of mistakes made by generals."
- "To the AFO personnel in Gardez and in the valley, Trebon’s move to have TF Blue take over the operation was ill-considered and appeared to be motivated by professional jealousy."
- "The selection of Hyder to command and control the SEAL elements in Gardez was a strange decision on the part of Captain Joe Kernan, the Task Force Blue commander."
- "(Despite repeated requests, Trebon, Kernan, and Hyder were not made available for interview for this book by U.S. Special Operations Command.)"
- "It is a reconnaissance axiom that a recce team should never infiltrate by helicopter directly onto its observation post, because doing so essentially signals the team’s location to the enemy."
- "Yet again in Anaconda, senior leaders’ failure to establish a tight, unified chain of command was adding unnecessary friction to that which is inevitable in any combat operation."
- "Suddenly another voice came on the radio, that of Brigadier General Gregory Trebon, the TF 11 commander, who was a few hundred meters away in the TF Blue TOC. “We don’t need you getting all worked up on the radio,” the Air Force officer told Jimmy condescendingly."
- "Trebon was making a decision he would come to regret."
- “They had a lot of heat, a lot of general officers and colonels pumping them for information and offering advice, and they had the least SA [situational awareness] down there in their cave,”
- Again, the decision to take Blaber out of the command chain was revealed to be a terrible mistake.
- “Whatever you do, don’t send them back to this same LZ,” he told Naler. “It is absolutely hot.” It was a message that was sent from Masirah, but never received.
- This wasn’t just the view of those on Takur Ghar. Juliet Team, who watched and listened to the entire battle, also reported up the TF 11 chain of command that the LZ was secure and the casualties could be medevaced. But it was not to be. At least, not until it was too late for one more brave airman.

Profile Image for Lawrence Roth.
221 reviews10 followers
November 19, 2025
Sean Naylor is a remarkable talent at war reporting. The only other book I've read of his was Relentless Strike, his history of Joint Special Operations Command (JSOC) which I read possibly a decade ago but remember being very impressed by. I came away convinced that Naylor was the type of researcher/writer/journalist who you could depend on to get to the important details of whatever topic he was covering.

Naylor wrote Not A Good Day to Die before Relentless Strike. He was apparently embedded as a journalist within the units that took part in Operation Anaconda. The combination of his first hand experience plus the impressively lengthy list of interviews and research he had done for this book has clearly paid off in possibly the best analyses of a military operation/disaster that I've ever seen.

You learn more from when things go wrong than when things go right. This is an important concept for
militaries to acknowledge of course, but upon reflection, I realize many of America's greatest war stories are disasters, and many of America's military disasters that I've personally read about have valuable lessons to teach people who are in a MUCH BETTER POSITION TO USE THESE LESSONS THAN ME.

To go down the list off the top of my head:
George Washington's leadership during the hellish winter of 1777-1778 in Valley Forge and the refusal/inability of the Continental Congress to fund, feed, and clothe their own soldiers throughout the entirety of the Revolutionary War teaches the military student about the value of effective quartermasters (Nathaniel Greene likely saved America during Valley Forge), and the price paid by the common soldier when the government does not support them.
We Were Soldiers Once and Young by Harold Moore teaches the military student the risk of conducting a search and destroy operation in enemy held jungle with no idea of the enemy force or disposition. Moore's air cavalry basically dropped hundreds of troops into what would turn out to be a shooting gallery in which they were surrounded by thousands of NVA and Vietcong fighters. Rescue was complicated by the sheer size and ability of the enemy force to continuously inflict major casualties on US forces. It should have also been a lesson that helicopter assault troops were not some terrifying, invincible force to US adversaries, but rather a threat to properly adapt to and study.
Black Hawk Down by Mark Bowden teaches the military student the risk of conducting a capture or rescue operation in enemy held urban environments with little idea of enemy force or disposition. The Rangers and Delta force that were caught in the fights in Mogadishu were forced to hold positions until evacuated, just like Moore's troops in the Ia Drang Valley. Those rescue troops were often tangled up in their own firefights, just like Vietnam. There are also lessons in there about the cultural friction between the Rangers and Delta, how high command screwups and miscalculations cost lives, how aerial recon and intelligence observation sometimes just does not cut it for a fast-evolving operation on the ground, and a few others I'm forgetting here.
The Lone Survivor story featuring Navy SEAL Marcus Luttrell, the sole survivor of his four man team which was caught in a vicious firefight on Sawtalo Sar mountain as part of Operation Red Wings, teaches the military student about the risks of reconaissance and organizational friction. Outside of Luttrell's personal account, Ed Darack's Victory Point book expertly picked apart the flaws of the Operations Red Wings and Whalers, including the cultural friction between the Marines and the SEALs, the completely separated and compartmentalized chains of command that both forces had in general in Afghanistan, the assumptions about on the ground conditions, flawed intelligence on enemy displacement, and complications in mission continuity (the main objective of locating and killing Ahmad Shah was put on hold in order to rescue Lutrrell and locate the bodies of other SEALs and aviators).

It is shocking, then, when Naylor matches Ed Darack's excellent investigative reporting and reveals that Operation Anaconda was so incredibly flawed that it's genuinely a miracle more Americans didn't die on Takur Gar mountain and in the Shahikot Valley. The lessons of most of these previous military disasters were spinning through my head as I turned the pages on this massive volume. THIS IS A GENUINELY FRUSTRATING READ in that Naylor does an excellent job at showing the calamity that will unfold. Nearly everything goes wrong in this operation. The chain of command between Task Forces, Mountain, Rakkassan, Rangers, and Air Force units was so tangled I could not actually believe what I was reading. It was actually worse than the command and control friction in Victory Point. Incredibly aggressive deployment moves like putting Rakkassan soldiers into valley floors where they would be fired upon from high ground ridgelines or dropping off SEALs and Rangers onto the peak of Takur Gar screamed of the helicopter assault arrogance and surrounded-on-all-sides consequences of Moore's book. Being prevented from sending quick reaction forces in to rescue troops in contact, or having those QRF shot down and killed, was so obviously Black Hawk Down it was ridiculous. All of this chaos as well caused by fragmented chain of command, sensitive egos of military leaders that possibly went all the way to the top, and the underestimation of Afghanistan's biggest set piece battle as a winding down operation when Iraq was coming down the pipe.

There was even a remarkable moment when one of the AFO teams had planted themselves on the side of a mountain, and encountered a goat herder who almost walked into them. "That could have been very bad" is what I imagine Marcus Luttrell and everyone involved with Operation Red Wings would have said had they read this book.

It's not just these lessons from other books of course. It was the failure of radios to work, the crowded air traffic that interfered with being able to give air support, the fact that mortars weren't brought into the valley during the first wave of Rakkassan infiltration, the fact that truer intelligence on enemy numbers and disposition was ignored because the operation just couldn't change due to ego and organizational friction, the fact that artillery and multiple attack helicopters and lots of other military resources were denied entry into Afghanistan because it would have been too much commitment, the friendly fire incident where an AC-130 gunship fired on special forces and their Afghan partners, which precipitated a near panicked full scale retreat when those same Afghan forces came under heavy Al Qaida mortar fire, and more. I could genuinely go on and on. But I don't need to. You need to read this book, because it's remarkable and ridiculous and boy does it point to several reasons why the United States was unsuccessful in its grand strategic mission in Afghanistan in the first place.

A last semi-interesting note: for those of you who were instilled in the military first-person shooter craze of the 2000s and 2010s like I was, you may remember Electronic Arts releasing a rebooted version of its Medal of Honor series. The 2010 videogame called Medal of Honor (how original) is clearly based on the events of Operation Anaconda. I haven't played it in a while, but I remember driving ATVs through the Afghan wilderness, controlling "Tier 1 operators" that were split in to AFO teams. I remember witnessing the AC-130 friendly fire incident on Afghan allies, and the SEAL operator falling out of the helicopter on the mountain. Hell, this book dragged up a memory of one of the mulitplayer maps in which a downed Chinook helicopter was a spawn point for the American faction. The campaign clearly ended in tragedy like the real life Operation Anaconda, and I suppose after all these years I figured I'd finally learn the real truth about it. My god did this book not disappoint.

Overall, an incredible military history and forensic investigation of a military disaster. It's a bit slow in the beginning as Naylor is introducing seemingly every single goddamn unit in the country, their commanders backstories, and other rather bland details that just get jumbled together. But as the operation gets the go ahead, the book becomes unputdownable.

This, and every other book or operation I listed in my review, has to be REQUIRED READING FOR ANYBODY IN ANY MILITARY ACADEMY. I swear to god, the next time the United States enters into some sort of military disaster, my first guesses as to how it happened are going to be inter-organizational friction and uncoordinated chains of command. This book genuinely hurt my opinion of the Navy SEALs and of special operations command mainly because of their arrogance but for a myriad of other reasons. What a remarkable read.
Profile Image for Jack.
240 reviews26 followers
September 4, 2017
Well written with significant inputs from the men on the ground. Anaconda was the first action for us in a generation. Elite us Airborne, Ranger, Delta, SEAL, SAS, and not-so-elite Afghans moved into the Shahikot valley expecting Al Qaeda to surrender after realizing they were hopelessly surrounded. Well, the enemy gets a vote. 100-300 enemy forces turned into about 800...with crew-served weaponry. They kindly declined to surrender and put the Rakkasans through their paces. The battle unfolds similarly to Mogadishu except the urban miasma of the Mogue is now the hinterland of Afghanistan. Several helos are shot down. Command and control, specifically unified command, is lacking resulting in missed comms and casualties. It is a wake-up call to us that Afghanistan is not over. The enemy is willing to go head to head with the firepower of the US military. They are willing to take the casualties. This is a signal for us that decades of war are around the corner. Radical Islamic fundamentalists will be our enemy from now until...well we do not see that clearly into the future. Nonetheless the war will go on.

I highly recommend anyone interested in US arms to read this book. A book about the beginning of our Islamic wars.
Profile Image for Don.
151 reviews
November 3, 2010
Fascinating read about the early stages of the war in Afghanistan. Naylor does a good job of presenting the events, decisions, and players leading up to Operation Anaconda and the ensuing... outcomes. The book shows the perils of command and control (C2) from afar and how relying too heavily on limited information (even nifty images from UAVs) can lead to poor situational awareness and bad decisions. Naylor tries to stay out of the blame game, but his opinions on that front do leak through at times. It's amazing what the men on the ground were able to accomplish despite C2 shortcomings.
Profile Image for Homira.
35 reviews15 followers
March 9, 2017
Excruciatingly painful level of detail although or perhaps because it was so well-researched, but I couldn't get past first 1/2 of book. This is probably excellent journalism but reads more like an after-action review or lessons-learned report. I'm normally a military/battle junkie and an Afghan. Loved Sebastian Junger's War and First In.
294 reviews4 followers
August 30, 2025
Great read about one of the first large operations the US military conducted in Afghanistan. Well researched and well told, this story of an ad hoc task force assembled without previous training experience together, the opportunity to conduct joint rehearsals, or even a single operations order directing all tasked units is full of lessons we must learn from.

There are many, but a few that stood out to me:
- Clear command and control relations must be established early, clear defined, and adhere to the principles of unity of command and unity of effort.
- Cohesion enhances lethality. This starts during training and should be built all the way through the rehearsals immediately preceding an operation.
- Flat, fast, effective communication saves lives. Without it, people die that otherwise could have lived.
- Organic indirect fires are hard to replace. (Note: I think this principle holds today even with drones. Small unit sUAS could potentially provide similar effects but it is hard to replicate/replace artillery)
- Trust the guy on the ground; they likely know better than any displaced HQs what is happening.
- Simple is usually better.
- Listen to intelligence reports that contradict your beliefs about the situation. They may be wrong, but dismissing them outright demonstrates arrogance and is irresponsible.
- Rehearsals are essential. This includes your communications plan.
- The enemy always gets a vote. Sometimes the weather and our the environment is your enemy.
- Physical fitness and mental strength (grit) matter.

Had it not been for the tenacity and skill of service members on the ground and a few aviation assets, many more would have died. As it was, too many died.
1 review
February 25, 2025
Very interesting perspective, goes well with "The Mission, The Men, and Me" as well as "My Share of The Task" and connects them. It also made highlighted a lot of the finger-pointing that happened during the operation.
Profile Image for Nicolas Hromyk.
6 reviews
October 15, 2023
Very informational, and very well researched, but holy moly what a slog to get through. Best read as a sleep aid in small sprints.
Profile Image for Brook.
919 reviews32 followers
May 18, 2016
2.5 stars, putting me in the minority.

This reads like a 450-page After Action Report, with a little bit of romance novel thrown in. I'm not some bloodthirsty, kill-'em-all gore hound, looking for guys gunning down faceless bad guys like Rambo. I'm fine with a battle/war narrative that is mostly logistics, background and movements. This book is as much Congressional Investigation as it is narrative. There is a lot of "who's fault was this" and "figure out what happened after the fact" that took me out of the story. By comparison, Last Stand of the Tin Can Sailors, which I just finished, managed to explore mistakes and savvy decisions without pulling the reader out of the story as much as Naylor's book did.

But what *really* pulled me out of the story were descriptions of the soldiers, Marines and sailors that could have been plucked out of Fifty Shades of Gray (I'm guessing). "Captain Smith was a rugged, muscular man, with bulging arms and chest, steely blue eyes, a full, luxurious beard, and the sort of deep gravelly voice that could stop a charging bear."

Clutch the pearls!

While the above "quote" does not actually appear in the book, many like it do. Without fail, the operators on the front lines are described as (and no doubt are) extremely physically fit, intense, steely-eyed guys with brass hangers. Again, I have no doubt that that's the case. But the tone, for me, was just a little quizzical-dog-head-turn off, and the descriptions were repeated for different team members enough times that I was groaning by the 5th or 6th one. On to the story...

Naylor manages to spend very lengthy passages describing events that might take place over a short period of time, or introducing facts that do not end up being relevant to the larger story. Again, something that is good for an AAR, where all actions need to be accounted for, but that don't advance the story. Spending a page and a half describing a position where two al Qaeda fighters are holed up, from their dress to their armaments to their fortifications, is very interesting. "And then the lieutenant called in an airstrike and wiped them off the face of the earth." No doubt it happened, but it does not tell me anything about the larger conflict other than "and then this happened."

We are given descriptions of the service members down to their gaze, which would seem to indicate the desire on the part of the author to have us empathize with them or understand them on some personal level, but then they are treated as chess pieces, for the most part. We are given "personal" data that is largely irrelevant to the story, and then it's troop movements and airstrikes after that.

It'd be like writing an Executive Summary of a business meeting you had with an outside vendor to be read by your boss, and starting off with what color tie everyone had on, and where they usually at lunch, and then describing the vendor's plan to modernize your payroll system. A diary entry might include tie color, but an executive summary will not.

If you are reading this book to understand Operation Anaconda, you will find much of what you need here. It is, if accurate, a good reference source. If you are reading this for a narrative, look elsewhere. It gets 2.5 stars because anytime I hear tales of cunning, courage, and general damn-the-torpedoes mentality, it's good to read about.
Profile Image for Chris.
779 reviews10 followers
November 22, 2020
An excellent book filled with combat, adrenaline rushes, and an understanding of how the USA went from fighting a proxy war in Afghanistan via the ODA Teams of the Green Berets to a larger footprint with >100,000 troops and bases, COPs, FOBs, etc.

I highly recommend this book.
Profile Image for Jerome Otte.
1,913 reviews
March 25, 2016
A great, engaging history of Operation Anaconda, with a stress on its infamous command difficulties. The flow of the narrative is smooth, all of the players are fleshed out, and Naylor admirably sorts out all of the decisions made and actions taken.

Naylor describes the problems in running a battle from thousands of miles away and the effect of Rumsfeld’s and Franks’ desire not to put huge numbers of American soldiers on the ground. He describes the confusing command relationship between CENTCOM and 5th Special Forces Group, the lack of coordination between the SEALs and the Rangers, and how American forces often fought according to the plan rather than on-the-ground conditions, although improvisations were eventually made.

The book starts off pretty slow, though, the ending is abrupt, and I’m not sure why Naylor or the publisher thought that title sounded good.
Profile Image for Gordon.
642 reviews
October 2, 2011
An outstanding, contemporary history of a short, but significant battle fought in the dead of winter in 2002. As I am currently based in Gardez and regularly fly over the Shahikot it was an extremely interesting read. Sean Naylor does an outstanding job of setting the scene and bringing the protagonists, their decisions and actions to life. The only thing that could have made this better would have been to include testimony of some of the Al Qaeda participants in the battle. Sean superbly highlights numerous lessons learned by the conventional and special operators, and by the tactical and operational staffs in his narrative. Lessons that are pertinent today and will remain so for years to come. A must read for any inbound task force or regional command.
Profile Image for Stephen Ritchie.
Author 1 book3 followers
September 2, 2016
Not a Good Day to Die is an excellent account of Operation Anaconda that lays bare many of the organizational and communication problems that plague large-scale operations. There were clearly many involved in the operation who knew their job and performed it admirably. However, mistakes were made. The mistakes made and lessons learned are very well presented and described. These are important when trying to understand the key principles and failure modes that underlie command, control, communication and intelligence.
Profile Image for Joe.
556 reviews20 followers
November 20, 2008
This book was okay. It is not very unbiased and a lot of what he chose to write about was only part of the story. I know a lot of the people that he wrote about and sometimes he presents an accurate description but sometimes he is pretty far off. It's worth reading however if you have no idea what has been going on.
206 reviews5 followers
Read
June 21, 2009
good dense,thorough,detailed, and descriptive
Profile Image for Neil.
1,311 reviews15 followers
October 15, 2017
I read this book partly out of an interest in reading it and partly because I chose it for a report for a class I was taking. I found it to be an interesting book, overall. There was a lot of detailed information in the book, and the narrative focuses primarily on the 'build-up' to the mission and then the first three days of Operation Anaconda (in the author's mind, the battle was already wrapped up after the third or fourth day, and the following couple of weeks were more political posturing and attempting to show the Afghani allies/forces as being triumphant against Al Qaeda). While the author definitely seemed to be biased towards particular groups and individuals, I still felt that he did try to be "unbiased" in most of the book. I had the distinct impression that some of the frustration that came through was because of how the chain of command became muddled and the problems with communicating that occurred before and during the operation itself.

The "biggest" part of the book is focused on the build-up to the operation. He discusses how the men trained, how information was acquired, and how the officers in charge attempted to get around limitations placed upon them by superior officers (including Cheney) who felt they "knew better" than everybody in command below them. Another "issue" was that the upper echelons of command felt that the "War" was "already over" and Afghanistan was more of a "sideshow" that did not require a lot of support or military personnel. There were also "political issues" that the lower-echelon commanders might not have been aware of (such as the desire to NOT to appear to be invaders or conquerors a la the Soviets in 1980 and the decision to NOT use artillery or helicopters extensively, at first, because of the damage caused by Soviet artillery and helicopters during the Soviet invasion and occupation). As the operation grew in scope, greater expectations were placed on the men involved. These greater expectations were directly contrasted with the lack of support or materials that could be used to ensure success. There were numerous communication issues, as well, up and down the chain of command as well as the structure of the chain of command of the operation. It also describes how special operations forces in conjunction with Afghani allies moved into the valley to figure out the lay of the land and what forces would be opposing the Americans and their allies.

The second part of the book deals with the first twenty-four hours or so of the operation. It details the craziness of that first day, how very little of the operation went according to plan. The "biggest issues" of the day seemed to be (1) the inability of the ground forces to communicate with the support aircraft overhead, (2) the chain of command being subverted further as officers hundreds and thousands of miles away attempted to micro-manage the battle from afar, (3) Afghani units not operation as promised, and (4) not enough flexibility being built into the plan (especially as the plan failed once contact was made with the enemy). This is not to say the American forces and some of their Afghani allies did not fight gallantly against their opponents; the American forces did fight gallantly. The frustration stemmed from the fight being more difficult than it necessarily needed to be due to the limitations placed upon the soldiers by officers further up the chain of command.

The third part of the book focuses on the helicopters that were shot down atop Takur Ghar as well as the rescue missions that were enacted to get the men to safety. The "biggest thing" I took from this section was, again, the lack of communication. That, and the author does not seem to think too highly of SEALs. The decision was made to establish an outpost on the mountain to act as some kind of overwatch for the American forces as well as to spy out enemy positions for subsequent air attack. The SEAL team failed to communicate with any officer related to the operation and acted, essentially, on their own in terms of attempting to find a place to land so the SEALs could disembark. Because of the lack of communication, the helicopter landed in the middle of an outpost of Al Qaeda soldiers and was promptly attacked, causing a SEAL to fall out of the helicopter as it attempted to leave the area post-haste. Because of the lost soldier and downed helicopter, rescue teams were sent out to recover the men and bring them back to safety. Two more helicopters were shot down, and several men would die over the course of these "rescue attempts" (partly because of misunderstanding with Headquarters as HQ failed to understand that a (relatively) safe landing zone had been established that would allow helicopters to land in relative safety). Helicopters were sent back in overnight to bring the various soldiers out (the walking, the wounded, and the dead).

The "final" part of the book essentially wraps things up. The author expresses his opinion that the battle was over after the third or fourth day, that most of the surviving members of Al Qaeda had already withdraw before Afghani allies were brought in to "finish" the battle after the heaviest fighting had already occurred. The opinion of the upper echelon commanders had changed as well, and the men who were sent in to reinforce and replace those already in the valley came in heavily armed and prepared to fight (unlike the first teams of American soldiers who were not expecting the severe battle which erupted).

I know the book focuses primarily on the Americans and their Afghani allies, but at one point it was mentioned that an Australian SAS team was allowed to join the mission because they had their own vehicles to transport the men to and from the battle, yet no mention is ever made of them again, after that point. I have read that other nations were involved in the battle, but I have not yet found out if that was during the period covered by the book or afterwards (in the "mopping up" period that the author seems to discount). I cannot decide if the "failure" to mention these other teams was a weak point or not; it would depend on when these other teams entered the valley in relation to the time period covered by the author.

I did enjoy reading the book. It was very informative, and it had an incredible amount of information needed. The author gives some backstory (backhistory?) on many soldiers in the narrative, and I thought it worked (for example, we are told the backstory of a sergeant who takes command of his platoon after the officers are either killed or incapacitated; we find out he was a former supply sergeant and this was his first time acting in a "command capacity" and how he excelled at it. Had we not known of his prior background, the reader would not have known how impressive it was that he was able to take command like he did or that his unit performed successfully during that time). It does get a bit long in the tooth at times (especially how he focused on the "build-up" to the operation and the amount of frustration that was prevalent during that time as the expectations of the operation increased while the amount of materials, men, and support available decreased).

I had intended to read the book at some point in the near future; having to read it for an online course accelerated the point at which I was going to start reading it. I am glad that I read it; it was an informative book, and it was a "good" book (in my opinion).
Profile Image for Tyler Standish.
437 reviews
March 15, 2017
What a fantastic book! I haven't read such a compelling war story since We Were Soldiers Once...And Young. The author does a great job of highlighting the courage and the sacrifice of almost every soldier, sailor, and airmen that participated in Anaconda, but it is perfectly balanced with the mistakes that were made along the way that cost the lives of numerous heroes. The lessons presented in this book are applicable at every level from tactical to strategic - the proper use of combined arms; the need for robust fire support from mortars to close air support; unity of command and when not possible, unity of effort; massing of effects; situational awareness; main effort / supporting efforts; controlling the high ground and other key terrain. However, it is always a shame that we have to relearn these lessons with the loss of blood and treasure.

Additional thoughts:
There was a strict cap on the number of regular military troops that were allowed in Afghanistan in 2002, set by CENTCOM. The reason for the cap was to not invade Afghanistan in the same manner as the Soviet Union. When the 101st deployed this put their attack helicopters and artillery on the chopping block.

The command structure for operation Anaconda was jury rigged from the beginning.

Even after several requests for artillery Operation Anaconda went on without and it was never addressed at the general officer level. All fire support would have to come from CAS and the few Apaches that the 101st brought with them, but the 10th Mountain Division Headquarters didn't have their air planning staff in theater.

Leadership by VTC is a symptom of micromanagement.

Task Force Hammer was never treated like the main effort of Operation Anaconda.

"Once we got the mortars firing we owned the battlefield."
Profile Image for Gregory Keeney.
4 reviews1 follower
January 23, 2020
One of the earliest accounts of the war in Afghanistan launched by the US military in revenge for the attacks on America on September 11, 2001. Sean Naylor's detailed narrative of Operation Anaconda is gripping, taking the reading into the tactical operations centers of the Joint Special Operations Command, specifically Delta Force, SEAL Team VI and their accompaniment of resources, & the 10th Mountain Division and 101st Airborne (Air Assault) Division, as for the first time in over 10 years special operations and conventional forces worked on the same battlefield to close with and attempt to destroy Al-Qaeda and Mujahideen fighting positions in Afghanistan's Shahikot Valley. Sean expertly details the lunacy of the "hodgepodge" command structure, and disjointed planning & resource allocation at all levels, as everyone senior military leader wanted a piece of the action. They violated their own teachings (combined arms training/planning) and specific principles of warfare (simplicity, unity of command, economy of force) in an effort to "get in the only game in town." America's enemy would live to see another day, mostly, but the toughest lesson captured by Naylor in his book is the harden fact that experience is a "MF" to the inexperienced American Soldier willing to die for their nation.
Profile Image for Derrick.
279 reviews5 followers
March 21, 2024
Wow, how this book caused me to dislike people I will never meet and have absolutely no bearing on my life at all. I knew of Operation Anaconda and what we learned as a military from the mistakes that were made in this operation. This was my first time really diving into a lot of the details. I was surprised, maybe surprised isn't the right word but for lack of a better word, at how when hearing some of the decisions and the friction and fog of war was going on of knowing there were decisions made that were just awful and directly cost peoples' lives. Wives who no longer will have a husband, children, who will no longer have a father. I could tend to get really worked up about a lot of this.

It was a good book though, and I enjoyed it. When I would get home at the end of the commute after having listened to it for 20 - 45 minutes, depending on traffic, I would be fired up! I'd recommend this to someone who enjoys military stories and hearing about what some have been able to accomplish. I felt like the author has a large disdain for SEALS from listening to the book though. That disdain seemed to shine through very clearly and maybe for good reason because of some of the decisions made during this operation, maybe because he just had a previously bad experience, I don't know.

5/5 recommend the book though, it was good.
438 reviews5 followers
November 19, 2021
First my gripes. It's "free rein" not "free reign". It's also "report" not "report back".
The split infinitives make me crazy ~ with almost every author, not just Mr. Naylor. "Every American put his head down." NO! Every American put down his head. Grrr.
This book is the adjunct to "Roberts Ridge" and it doesn't really matter which order you read them.
This book is also the Afghan version of "Black Hawk Down". Eventually, it is gripping.
Mr Naylor is very thorough. He has done his homework, of that there is no doubt. He interviewed a great many people and he was actually IN Afghanistan for some of "Operation Anaconda" judging by the photo with the bigwigs of the operation.
That the operation was a clusterf**k is of no doubt and illustrates how important communication is in any situation, especially one where lives are at stake. No matter if you're Army or Navy, striped or plaid, one needs to include, rather than exclude, ALL divisions involved in any vital operation.
Mr. Naylor did a creditable job of presenting the facts and the backstory of Takur Ghar and those involved in Operation Anaconda. Highly recommended.
Profile Image for Joshua Greer.
40 reviews1 follower
July 24, 2017
An excellent book with great lessons learned about fire support, coalition operations, unity of command, and American hubris. Highly recommended for field grade and senior company grade officers.

Naylor has written a few good military history books and generally does a very good job. This one is a very good analysis of the planning and execution of Anaconda that occasionally gets bogged down in the "who-shot-John" level details of battle. While interesting for many readers, someone who is interested in the regiment level planning doesn't really care about individual soldiers and their stories of shooting individual enemies. That being said, the occasional vignette at the soldier level does keep the reader engaged.
Profile Image for Bill Conrad.
Author 4 books10 followers
March 21, 2018
Not A Good Day To Die was an amazing book and it highlighted a story that I was unaware of. This book was gripping from page one. The team experienced every possible type of problem and nothing seemed to go their way. Slowly they learned the land and the people who lived there. There were several touching stories about interacting with the locals and it was nice to see the military portrayed in this kind light. When they began engaging the enemy, the fighting was fierce and effective. This was a perfect example of what the right people could do, with limited resources at the right time. Sean Naylor did a wonderful job of capturing this important event. The story was well presented and it made for a fantastic read. This book in on my list of books to read again.
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