Punching Out: Latest ‘Dear Boss’ Letter Decries Air Force’s Lack of True Leadership

Punching Out

The Air Force is in the throes of a pilot retention crisis. Not a problem, issue, dip, or down-cycle, but a full-blown crisis. The service is several dozen squadrons worth of pilots short of what it needs to successfully perform and sustain its mission. That shortage is worsening by the day as each pilot arrives at the career crossroads, assesses the options, and promptly makes the decision to bail out.

While this crisis packs increasing risk into the national defense portfolio, Air Force senior leaders dither and bumble, somewhere between confused and paralyzed by an issue that should be crystalline to them. Lt. Gen. Gina Grosso, the Air Force’s chief of personnel, went before Congress to discuss the pilot shortage recently and seemed to have less to say on the matter than her Marine and Navy counterparts who have far less at stake and shortages far more mild. Her brightest idea thus far? Ask the airlines to stop wanting our pilots so badly … and being so willing to treat them better.

While she and other generals misapprehend the crisis as a cash flow issue or something they can cure with policy memos, the rank and file have been doing some thinking of their own. Turns out they also care about the shortage … because they care about the Air Force. Turns out they have their own ideas about the nature of the crisis — ideas that make a lot more sense.

Some people believe this crisis has a dominant cause. A root cause. I happen to think they’re right … because in a military organization, all crises have the same root cause: a failure of leadership. Sometimes a failure of leaders to anticipate, listen, or react appropriately to facts. Sometimes, the failure is more fundamental and systemic … a failure of leaders to foster an operating environment capable of attracting and retaining the talent necessary to win. 

On that score, I think this letter nails it. If Gen. Goldfein wants to win, and I’m sure he does, let’s hope he reads and internalizes every word of this letter. Time to act on it is running short … and when that last grain drops in the hourglass, we will have last the next war before the first shot is ever fired.

Read, respond, and share freely. 


Dear Boss,

I’ve fucking had it. I’m finally giving up on my Air Force and I’m throwing in the towel. Flying fighter jets is no longer cool enough to outweigh the bullshit, and so I’ve broken the mach for the final time. You’re going to believe that I’m leaving because I’m tired of deploying, that I’m sick of the queep, and that I seek the money bags and greener pastures of the Airlines. I’ve heard you on TV spouting those same lines over and over. Boss, I probably will join the airlines, but that’s not why I’m leaving. I’m leaving because my wife (I love my wife) got tired of hearing me come home every night and bitch about how the leaders of my Air Force are running it into the ground. I’m leaving because you took the coolest job on the planet, you, the leaders of this job, and you ruined it. You took one of the few jobs left in the world that kids hang posters of on their walls, and you made it so damn miserable that thousands of guys like me are calling it quits. And the worst part is, you have no idea HOW you made it miserable, and even less of an idea how to fix it. You are focusing on the second and third order effects, but not the root cause.

Boss, you were a fighter pilot. You were trained for years in how to identify the root cause. I know you have the ability to dig past the airlines, ops tempo, queep, and other reasons you’re currently focusing on, and find the DFP. I know that you know what it is, I just don’t think you have the stones to call it out in public and do something about it, so I’m pulling the handles.

Yes, life in my Air Force has gotten tough. But the real reason I’m leaving boss, the heart of the issue is this. I’m a leader, I always have been. People follow me because I’m good in the Air, I have a strong act in the bar, and I give a shit about the people that work for me. And because I’m a true leader, I will never lead in this Air Force. Instead, the guys that are leading in my place, and in the place of all of the others like me, are boot-licking, risk-averse, yes men who have spent an entire career being faithful followers and couldn’t lead a 2 ship to the end of the runway. They’ve been rewarded their entire careers for being non-confrontational, making only safe decisions, punishing downhill and protecting uphill, and most importantly, being loyal to the bad leaders above them.

That’s the real problem here, boss…. loyalty has become the new CURRENCY of your Air Force. More than integrity. More than excellence. More than tactical ability. More than taking care of the people in your charge. Absolute loyalty to your superiors is what gets you promoted. And in return for that loyalty, you get protection. Protection by your bosses for every stupid, unethical, illegal, hair-brained, vindictive decision you make that degrades morale, drives people out, and makes good leaders like myself write this letter.

As a result of decades under this bullshit system, boss, you’ve created the largest true leadership vacuum in the history of our Air Force. We’ve never been farther from Robin Olds than we are today. We could never pull off an Operation Bolo in today’s Air Force! No way we would take that risk! And it’s a self-licking ice cream cone! It’s only going to get worse, and you’re going to keep losing the real tactical leaders because they will never kneel, swear loyalty, and play the game! They know how the game is played, but they choose to do the right thing instead. They will never be blindly loyal to the toxic leaders in today’s Air Force, and neither will I. I’ll salute smartly and do my duty, but they will never earn my loyalty.

And what happens when we identify these horrible, toxic leaders, boss? Do we drive them out? No! we promote them! Our entire senior leader ranks work like a mafia crime family. Once you are a “made man,” you can literally take any action you want and you know you will be protected! We see it in our Air Force on a daily basis! Generals threaten their people with “Treason” for giving valuable input on the validity of combat airframes – they are protected and promoted. Generals tell test pilots that if they leave the Air Force in accordance with current guidelines, their careers will be “torpedoed.” They are protected and promoted. Generals take vindictive, uniformed, punitive action against their people, like they did to the FAIPS in molly-gate… they are protected and promoted.

At the wing and group levels, Colonels and Generals crush their people and fire anyone that disagrees with them–they are protected and promoted while their people languish. On and On it goes, a new story every week of a MADE MAN doubling down on his authority after making an uniformed decision, and without fail, being supported the entire way by his leadership. It’s criminal, boss, and I’ve had enough. It’s gotten to the point where any time I see a chicken or a star on a flight suit or ABU, I want to vomit.

Boss, I dare you to show me a single Colonel or General that is completely irreplaceable because of the quality of their leadership. I ask you seriously, all of these leaders that are oppressing their people and driving them out… what is so amazing about them that you can’t just sack them and replace them?? The higher in ranks you get, the easier you should be to replace. They aren’t maintaining any tactical or technical skills. So why have our Generals and Colonels become so valuable? So valuable that we will allow them to continue to make toxic decisions that are crushing our airman and forcing them out? You know the answer, and it’s why I’m leaving. Because leadership is a club. And that club protects itself. Protecting leadership is the most important part of the Air Force today, and it’s more important than keeping me around, Boss.

You ask yourself why we are all leaving… well, you’ll realize the answer when the only people left in the Air Force wearing flight suits are the CGO’s that can’t leave, and the protected senior leaders. The answer to the riddle of why we are leaving in droves, is the Air Force has to make a decision. What does it value more? Keeping pilots in the cockpit? Or protecting its senior leaders at all costs? You can’t have them both, boss. And until we start to see Senior Leadership being punished and held accountable for the way they’ve fucked up their charge, we aren’t sticking around. It’s us or them, and you’ve been choosing them for as long as I can remember.

Boss, you know that I’m right. But in case you don’t, then please assume that there are horribly vindictive Cols and Generals out there, that act illegally, unethically, and capriciously. There are toxic senior leaders that make horrible decisions. You have to believe that there are some. And if you DO believe that, then ask yourself a further question…. What the hell do the people serving under this toxic leadership do to get out from under it? How do they get help when they are oppressed by toxic leadership—who do they appeal to? I hope you don’t say the Inspector General. Because if we thought the IG could help us, we wouldn’t be leaving, we’d be sticking around and using the IG. But we’re not. Because we have figured out what you have known for a very long time… That the Inspector General exists not to help us escape the illegal acts of our toxic leaders, it exists to protect those very same leaders by identifying the hole in the dike, and allowing the senior leaders to circle the wagons and protect each other. The guys I’ve seen that filed IG complaints have consistently not found resolution. The only consistency they found was the reprisal that universally follows a challenge to “the club.” They’ve been stonewalled for ridiculous amounts of time. In cases that would take a group of rational humans a few hours to decide if a complaint warrants investigation, our IG system takes months and even years. Even if they determine a case has merit, they are extremely unlikely to even do anything about it. Rather, they will refer the complaint to another senior leader up the chain, after delaying for enough time to make the complaint a distant memory. Without fail, that senior leader will do what all senior leaders are trained to do in today’s Air Force… MAKE THIS HEADACHE GO AWAY. If I believed for a second that the IG was a watchdog intent on holding leaders accountable for their actions and keeping them from taking unethical and improper action, I would be staying in. But I don’t, and I’m going to the outside world, where these toxic leaders can’t touch me anymore.

Don’t believe me boss? Why do you think so many of our airmen are going to congress and social media justice warriors like John Q. Public? Is that because we are the whiniest generation of Snaps you’ve ever seen? I hope you aren’t stupid enough to believe that. It’s because as Colonels and Generals have grown more toxic, our ability to protect ourselves INSIDE the system has completely died. So we take our complaints to the only place we still believe desires to help us. We take it outside the system.

Good luck getting your issue taken up by Duncan Hunter and the other justice inclined leaders of congress… every week they have 10-15 more fights to make against your senior leadership mafia. They are winning them, but their case load has grown too large for us to all be heard. Good luck getting John Q. Public to fight your case for you… he’s too busy being the only voice out there that can actually hold toxic Air Force leaders accountable for their actions! He’s too damn busy to help us all! You want me to stay? Then do the jobs that congress and JQP are doing for us right now! If you want us to stay, THEN FIGHT FOR US, DAMMIT! Break up the damn leadership club and make them scared for their careers! Make the bad leaders leave, and you’ll keep us. As I said before, boss, it’s them or us. Who do you want miserable and leaving in droves… your operators? Or your toxic leaders? Pick one, and pick fast, cause we’re not currently sticking around to see if you make the right decision.

As I said before, you were a fighter pilot. You understand how to find the root cause. All of the reasons you’re hitting on for the mass exodus of fighter pilots have small arrows next to them, but they aren’t the root cause. The root cause is YOU ARE PROMOTING THE WRONG PEOPLE AND PROTECTING THEM AT ALL COSTS. Everything that’s wrong with the Air Force right now, everything that’s contributing to making people leave, it can all be fixed by promoting the right people, and crushing the wrong people. You can’t fix it yourself, boss. No matter how much you say the Squadron is the heart of the Air Force, you will still have Ops Group and Wing Commanders acting like squadron commanders and micromanaging their people. Your message will never make it past the same leadership club that you somehow navigated. They will dilute it and distort it and twist it to benefit them. You have to roll up your flight suit sleeves and get dirty. If you want to keep us around, you have to start making some cuts. Hell, if you actually declared war on toxic leadership, declared transparency and accountability as CORE VALUES, and vowed to break up the club, I’d stick around just to see it happen! Hell, I’d volunteer for a non-flying 365 to the desert just to watch it happen! I’d do extra queep just to be around when it happened! I’d eagerly do IDE and SDE if you promised me that I’d have a chance at leadership based on my abilites and leadership talents, and assured me that there was about to be a huge availability of leadership positions after you cast the money lenders out of the temple!

Boss, what do you have to lose?? Your legacy? Because no matter what you do while you’re running the show, your legacy right now will be that you presided over the largest voluntary rated exodus in the history of the Air Force! Unless you fix this, that’s what you will be remembered for! Instead, your legacy can be that you brought ACCOUNTABILITY back to the senior leadership ranks and sent a message to the entire force that everyone is under the same justice system. What do you fucking have to lose??? None of the guys you’re allowing to be protected really give a shit about you! They would cast you aside just like they’ve done to us in order to keeping moving up the ladder! Fuck them! Pitch into this fight and help us clear the lane!

I’ll close this up, boss. Not because I hear the bros singing songs in the bar and I’m late for roll call–because all we hear in the bar (heritage room, sorry), is the echoes of the days when the fighter pilot was king. We are in the death throes now. Even our young fighter pilots see it. They treat their time in the cockpit as a gift. A gift they know they will give up voluntarily before they are ready. They watch us old burn outs talk about the days when being a fighter pilot was everything we thought it would be. They watch us talk with great reverence of leaders that we followed to combat without hesitation, because we knew they had our backs—in AND out of the cockpit. They listen with amazement to the stories of our fuck ups, and marvel that somehow our careers continued. They cannot fathom a day and age where you could make mistakes and your leadership would punish you but not drive you out, because you were a valued commodity.

We talk with great respect about a time when our leaders were tactical gods, and made decisions without fear of failure. We tell them that being a squadron commander of a fighter squadron used to be the greatest job on the planet, and the only job we ever wanted, more important than being a general or colonel. They look at us with confused looks, because they have been taught even at this young age that all that matters is to continue to climb the ladder, at all costs, and at the expense of your troops, until you reach the club and are protected. They are taught this not by words, but by the actions of the Colonels and Generals. They learn from watching.

Boss. I want to stay, I really do. I love being a fighter pilot more than I’ve ever loved anything. But I know the end to this story. I know the Air Force doesn’t have the balls to call the baby ugly and risk the public exposure shit storm that would come about if it declared war on the senior leadership club. I’m tired of being terrified of what awaits me when I walk into the squadron. I wish it was our leaders that were terrified. Terrified that they have been given so much responsibility and authority—that they have been trusted with the greatest commodity known to man—that they have been trusted with the care of their airmen and if they fuck it up they will be punished. But they’re not terrified. They’re smug. They’ve run this ship into the ground and everyone is jumping off, and they’re aren’t sweating it one bit.. because they know that they will be protected. They got theirs, and that’s all that really ever mattered to them.

It’s been a good run. If you ever do turn it around, boss, let me know. I’ll drag my washed up ass back on base and straight to the nearest fighter bar and buy a round. I’ll bust out every fighter pilot song that I can remember. But I think you and I know that’s not gonna happen.
I do take joy in one thought though. I know that when I leave, none of my bros will shed a tear. There are still bros that are sticking it out and trying to make it better. And I know these bros, the TRUE leaders of the Air Force, would only have one thing to say upon hearing that I left. And that one thing is music to my ears… because it’s the ONE THING that I wish you had the guts to say to the toxic mafia running your Air Force into the ground…..


Knock if off.
See ya, boss. Time to drive the painted tube of shame…
“Gear Up… Flaps Up… Pudding Cup!!”

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