Judging Freedom - James R. Webb (Jim) : Will US Troops Kill Iranians?

Episode Date: July 24, 2026

James R. Webb (Jim) : Will US Troops Kill Iranians?See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Undeclared wars are commonplace. Pragically, our government engages in preemptive war, otherwise known as aggression with no complaints from the American people. Sadly, we have become accustomed to living with the illegitimate use of force by government. To develop a truly free society, the issue of initiating force must be understood and rejected. What if sometimes to love your country you had to alter or abolish the government? the government? What if Jefferson was right? What if that government is best, which governs least? What if it is dangerous to be right when the government is wrong? What if it is better to perish fighting for freedom than to live as a slave? What if freedom's greatest hour of danger is now?

Hi, everyone. Judge Andrew Napolitano here for judging freedom. Today is Friday, July 24th, former United States Marine Sergeant and current podcaster Jim Webb of the famous Webb family will join us in just a moment and I will ask him, will American troops kill Iranians? But first this. You know, just a few years ago, if you told someone you were stocking up on emergency food that would have called you a tinfoil hat conspiracy theorist, not anymore. We've all seen supply chain chaos, devastating natural disasters, inflation, war, civil unrest, and preparedness has gone mainstream. That's why we're so excited to partner

with my Patriot Supply, America's original Patriot Preparedness Company. Right now, they're celebrating America's 250th birthday with one of the best deals they've ever offered. Two hundred and $50 off their best-selling six-month emergency supply of food, available now at preparewiththejudge.com. This is the exact same survival brand trusted by over three million American families. Why? Because because they deliver 2,000 calories a day. Their food lasts up to 25 years without refrigeration. And it contains no GMOs or artificial colors or flavors. And you can count on it to keep your family fed no matter what happens.

Even at full price, it's still the best decision you'll make for your family. With this $250 discount, it's a no-brainer. Go to preparewith-a-judge.com to get your emergency food kit today. That's preparewith-a-judge.com. Jim Webb, welcome here, my dear friend, a pleasure to chat with you. Absolutely. Thanks for having me. Thank you. From your five-year experience in the Marine Corps and all you did there, do you have an opinion

as to whether American ground troops that would be Marines and Army are prepared to engage in a land invasion of... of all or parts of Iran. Wow, that's a big question, Judge. So let me break this down in a couple different segments for you. Sure. We have probably the most highly trained and capable Marines and soldiers on the planet. But the problem when it comes to invading a place like Iran is mostly it's very much on the logistics side.

It's like, okay, I keep hearing that we're going to put guys and Kesham or Karg or seize limited objectives on the coast. And I have no doubt that if we inserted them, they would be able to achieve their initial objective, which is the whole terrain. But the problem comes when you ask them to sit there and hold it. And this is an issue as old as warfare itself, because once you stop moving,

you become a static target. And in this particular environment, you're looking at logistical lines that are incredibly long. All of our bases, which usually support these types of, of operations in the region in Kuwait and Qatar. I mean, probably going all the way back as far to Jordan have been either evacuated or effectively blown up by the Iranians, which means the guys you put on the ground there, not only are you relying on probably primarily some sort of helicopter air-based resupply, which is very predictable. It hasn't worked historically. You can go back to something like Stalingrad to take a look at that or any number of campaigns.

D.M.B.Fu is another one. K-San, which was very, very, very precipitous. It was a very dangerous operation in which we eventually abandoned the base after. It doesn't really work. And in this case, you're talking about excess of 100 degree Fahrenheit heat on a daily basis, the amount of water you'd have to get in there before you used to have to worry about things like ammunition, food, and casualty evacuation. And all of these types of operations have a very, very deliberate type of approach where you go in. You have limited landing zones, whether it's a field or some kind of

air strip you sees that the Iranians obviously know where they are. And then you have to account on the flip side for Iranian capabilities and the fact they've been preparing for something like this for decades. And anybody who doesn't think that's the case can just take a look at the way that they have fought this war to this point. And they're doing it on their terms in a way which they have mapped out our capabilities and intent and approach for decades. So, no, it's a, it's a horrific idea. The Pentagon, as you understand it, which failed to take into account the likelihood of the closing of the Strait of Hormuz and its economic consequences.

The Pentagon, as you understand it, which failed adequately to protect American troops and assets in Gulf bases, which now have been harmed and large. destroyed by the Iranians, would the same Pentagon take into account the variables and logistical problems that you just articulated before it says to 10,000 Marines, go take that island? I mean, I would really hope so, Judge. I mean, it's so once again, this is a kind of a bifurcated issue, right? I believe the Pentagon knew exactly what the Iranians were going to do at the outset of this war. They've run war games on this. You go back to General Van Riper's war game on this in the early 2000s. And he predicted a wholesale annihilation of whatever kind of landing force we

were throwing in there. And that's before the Iranians had the types of capabilities they do now. The problem here is leadership. There is nobody in the Pentagon who's standing up and, you know, taking a hit for the team on behalf of their guys. There's, there's nobody saying, stop. This is stupid. And that's really your job. Is this because they're afraid of being fired by Hedgeseth if they dare disagree with him, even in a private conversation? Yeah, that's got to be it. judge. And it's it's cowardice. Wow. Wow. Do do the troops now I'm talking about guys like you who God God bless you you're not there. But if you were guys like you troops on the ground, do they concern themselves with why the U.S. is fighting Iran? Yes. I mean, it's it's

inherently part of the job, right? Now you've got to be able to separate this out. so you can focus on coming back alive and getting your Marines back alive, in my case, as a Marine. But yeah, you want to know why because at the end of the day, you're risking your life. And if you don't have a good reason to not go back to say your wife and your kids and your parents, that's going to weigh on you. That's going to affect morale. It's going to affect the entire way you approach these things.

I mean, think about this way, I guess in civilian terms. How would you react if someone came through your front door and threatened your kids. I mean, I know how I'd react. I would lay it all on the line unhesitatingly without question. But if it's a different scenario where like you see a guy on the street trying to take a bike and it doesn't really matter. There's there's no reason to risk your life for. This is similar. There's no threat to the United States. This whole thing was ginned up on behalf of Israel. And all the statements are out there going back to day one. And the guys on the ground know this. 100% and I have absolutely no doubt it impacts their morale and I wouldn't say willingness to do

their job because you don't really have a choice in that environment right you're you're part of the military you do what you say you have a completely different set of laws that govern you under the UCMJ you don't have a first amendment so you have to execute but at the same time it's going to it's very much going to impact your your ability to put it all on the line shall we say What is, if you know, the level of morale of the 50,000, I guess we don't even know the number. I should ask you the number. Is it 50,000 troops that are there? Now I'm counting, you know, medics and backup and cooks and everybody, not just ground troops.

Whatever the number is, give me an estimate on the number. And then tell me what you think the level of morale is. Is it like it wasn't Vietnam, which was terrible? Or is it something else? So, yeah, I think you're about right with 50,000. That is not 50,000 combat troops. It's the actual trigger pullers are probably roughly a third, a quarter to a third of that number. So we do not have a very large force on the ground that is capable of seizing much terrain,

let alone fighting the entire Iranian army on their own turf. Morale is low. I have talked to a number of people who are still on active duty or still in service of some kind. And this goes back all the way to February, where you had the rumblings of this conflict coming up. and they did not want to do it. It's one of these things where they were looking at a very capable enemy who they were going to start a fight with for a reason they didn't quite understand. And the biggest concern was that they were not fully prepared.

And if you look at the evidence on the ground, once again, with the effectiveness of the air war there, it's very clear that we did not have the assets in place to fully execute this. And everybody who is taking part in it knew it. Wow. Do the troops talk to each other? I know they don't have a First Amendment, right, but we're not talking about standing on a soapbox

and criticizing the president or the secretary of defense who calls himself the Secretary of War. I'm talking about chit-chat amongst the troops. Do they talk to each other about why are we here? And does Iran really pose an imminent threat to my family back home? I'm sure they do. I mean, I can go back to my own experience in Iraq to really break that down very simply, where there were some of us, myself included, who went over and understood, I mean, you know my dad,

he was against the Iraq war from day one. I was brought up with that and I went anyways because it's family tradition. But I understood the quasi futility of it or the futility of it at the time. And we had some people who were, you know, very much true believers in the George W. Bush line back then. However, by month X, I mean, not very long in, all that was gone. And people understood that what we were doing was not going to work. So you do talk. You see what's going on around you.

And, you know, they understand the polling here back home that this is the most unpopular war in American history, you know, but that's part of what, you know, it makes the military a great organization, you know, is that we have the ability in the military to filter out the noise and focus on the job. job at hand and try and go get it done. But I don't think there's any question at all that the troops on the ground understand that this is very unpopular and doesn't have any tangible benefit to the security of the United States. I don't know if you saw the numbers that Chris just put up. Do these numbers surprise you approve of the way Trump is handling the war, handling Iran, I should

say, 29 percent, disapproved 69 percent. I don't even know if LBJ had a number that low. I'm not surprised at all, Judge. I mean, this whole thing is such a debacle. I mean, we attack them on day one. We killed their leadership and an assassination. We killed the Ayatollah. And that's an unprecedented move in terms of how the U.S. portrays itself around the world.

And if you look at precedence for our actions around the world, we don't just go around assassinating foreign leaders. And the whole thing has been downhill. I mean, ever since, we've achieved no objectives. we have cratered parts of our own economy. And unless we pull back from this, we're standing on the abyss of causing a global depression. And that's unbelievable. That's an unbelievably nasty, self-inflicted wound.

And what we're solely focused on right now is opening the street of Hormuz, which is a problem we created that was completely predictable from the front end. And everybody see this. So when you see, you know, some 70% of the population, doesn't agree with the way this is being handled. I wouldn't be surprised if that's actually low, and they're giving, you know, the president a little extra credit, so to speak. Wow. I know you're not an economist and neither am I,

but we have a global depression. Gasoline prices are going through the roof. And the president's imposing 10 and 12.5% tariffs on almost every product coming into the United States. These tariffs began eight hours and 15, minutes ago at midnight last night at 12.1 a.m. actually, today, July 24, 2026. Do you think he recognizes what this will do with voters at the polls in November? He mustn't, I mean, because the ramifications are clear as day. You know, you look at any number of U.S. elections, and it becomes very apparent to

even somebody just taking a look at it as a hobby, if mind you, that Americans vote with their pocketbooks time and time and time again. You can go back to the first George Bush during the Gulf War to get a very clear picture of this where, I mean, what were his approval ratings at the end of the Gulf War? They were in the 80s. Yeah, 80s, 90s. And then he had that one slip up where he raised taxes. And boom, he was gone instantly replaced by conman in Bill Clinton. And this is this is historic historical arc. But more to the point, like, you know, there's the economic side.

But what I can't grasp is how he has completely forgotten his campaign promises. Like myself and any number of people voted for this guy because he had seemingly had the testicular fortitude to get up there and say, hey, we're not going to fight any more stupid wars. But here we are. We're fighting the dumbest war that we have ever fought. And it's quite possibly going to be the most destructive. So, you know, I think he had a chance to kind of pull out of this nosedive on behalf of the Republican Party probably a couple weeks ago when they first got the MOU done. Right. There was a chance.

But now, I mean, there's none. You know, he is ensuring a Republican blowout in the fall. You are a former rifleman in the Marine Corps. How difficult is it to kill somebody? Somebody you don't know, somebody who doesn't threaten you just because, they're on the other side. I mean, that's a, excuse me, that's a pretty, sorry, pretty difficult question to answer, judge, someone who doesn't threaten you, you're covered under the, you know, the rules of engagement.

You don't pull the trigger. You need positive ID. You need hostile intent in order to pull the trigger. And that's drilled into our guys over and over again. Granted, my situation was a little bit different because we weren't fighting a uniformed enemy. They were in tracks suits. They looked like the sopranos, we would joke, you know, military age males and whatnot. And you had to really go through a very rigorous escalation process of force to pull the trigger.

You had to see a weapon. They had to shoot at you. When you're fighting a uniform enemy, I imagine it's different. I wasn't there during the initial invasion. We were actually fighting the Iraqi army proper in uniform. But I would imagine it's a little more difficult for these guys to do their job. knowing that this situation is not above board constitutionally. It's not benefiting the American people at home.

But at the same time, when it comes down to it on the ground, you have an absolute duty to bring yourself and your guys back. And you'll do whatever that takes. And in the heat of the moment, if they're on the ground and they're getting shot at, it's sad and it's unfortunate, but they're going to do their job. They're going to pull the trigger. and they're going to take out as many people as they can in order to get their people back. Wow.

You just have to make sure it's worth it on the front end before you can make that. Right, right. From the outside, which is where you are now, because you're, I know you're a Marine forever, but you're not on active duty. Thanks to be, God. Oh, yeah. Does it appear to you that Secretary Hegseth understands the ramifications of what he's doing or to use the language of the streets that he knows what the hell is going on?

Not really. I think he's a very destructive secretary of defense slash war. You know, he's, I will give him a little bit of credit with his, at least his rhetoric to focus on lethality and to get past a lot of kind of the woke nonsense that's infiltrated the military over decades, really. But I don't know how effective that is in terms of the practical application of those policies. The military has unfortunately been a petri dish for social experimentation going back to, I mean, at least Clinton. But in terms of how does he understand like the effectiveness on the deck on the ground of what we're doing, he's either doing one or two things. He's either lying to cover his ass and keep his job by putting out these little propaganda videos and getting up there and talking about, you know, we have incredible magazine depth and all these different things.

or he truly does not understand the situation that the military is in. And if we commit any degree of ground troops, that will be a giant red flag. This guy has absolutely no clue. But overall, I think he has done a tremendous amount to undermine the credibility of his own office and of large aspects of our force through any number of his policies up there to be frank. Why did you join the Marine Corps, Jim? family tradition you know it's uh my grandfather my mom's ibo's on iwojima my dad fought in vietnam and i was going to join the military no matter what we go back to the uh you know the french and indian war in my family uh we've been here we fought basically as militiamen as citizen

soldiers the entire way through so it was uh it was duty and i picked the marine corps because it was my impression i was brought up probably very heavily propagandized in this in this regard that uh they were the best of the best um And if I was going to go fight in a war, I would be in the premier organization that takes care of its people and looks out for, you know, the guys on the left and the right. So that's why I choose them. And I loved every day I was in it. Would you encourage or even permit your sons to join the Marine Corps? No.

No. And I've, you know, I said this on Tucker show in March where I would absolutely not. Not at this point in time. I have a two-month-old son. I have two daughters. My wife was in the Army. And I would not allow them to join at this point. Grand, you know, it's like when they turn 18, you can, you only have so much say.

And they're probably going to do what you don't want them to do just despite you. Why would you discourage them? Because we're no longer fighting on behalf of America. You know, you just take a look at this war. There's, I hate to say it, but the people who have died have not died defending this country. They may have died, you know, for their buddies on the left and the right. But this war is openly being prosecuted for a foreign actor, you know, a client state that now runs our foreign policy. And that is not worth your life.

There are any number of things you can do. I do not want my kids dying for Israel. I do not want my kids dying for any other country. If they want to step forward and put their life on the line to defend our way of life, our constitution, what has been built in this country, my hats off to them that's my family tradition but that is not the case right now and i just i would never be able to reconcile with myself if they were to go do that and i was to enable it you know uh secretary heggseth uh referred to these poor 20 i guess it's up to 20 now people who died as heroes i don't think they were heroes i think they were sitting ducks they were

you know and it's um the the the the action i think there is heroism is thrown around a lot as a buzzword. And I'm not trying to take anything away from the dead. They definitely sacrificed themselves for an ideal. That ideal may have been deep inside them. But they were sitting ducks. They did not have proper protection in any area where they've been killed. And that is just, it's evident in the base fact that we did not have the proper air defense equipment in place when this kicked off. We did not have a plan. And it's all over the place. You can look at Jordan, you can look at Kuwait, you can look at Saudi Arabia, even in areas where we don't have KIAs or mass casualties, we are unable to defend ourselves from the most predictable and most probable course of action that the Iranians would use, which is their missile systems. This is no secret to anybody inside of DOD, DOW, if you want to call it that, the intelligence agencies.

We know their capabilities. They have been shooting these missiles in various forums, at least at the Israelis for years. And this speaks to a guy like Hegset, not being able to say, do his job and say, hey, Mr. President, you know, we don't have the assets in place to effectively defend our people or even really counter what they're going to do. And that's a failure of leadership. And that's on the people at the top 100%. You know, I've played this a couple of times this week, but I love. for your comments on it. It's about two minutes long, but it's a very telling, grilling of Secretary Heggseth by Senator John Ossoff, and I'd like you to comment on it. You'll cringe a few times. Chris, cut number nine, please. On day 14 of this conflict, Mr. Secretary, day 14, nearly five months ago, you stated that Iran's military had been, quote, destroyed and quote, made combat.

ineffective that was on day 14 of the war was that an accurate statement they didn't have a Navy any longer it's completely sunk their missiles were buried underneath a lot of their underground facilities and their defense industrial base has been almost completely destroyed on day 14 of this conflict in the second week of the conflict you stated that Iran's military had been quote destroyed and quote made combat ineffective was that an accurate statement yes or no Iran's a to challenge the United States of America at the level of which we're capable of. That's not what I asked you, Mr. Secretary. You said on day 14, Iran's military had been,

quote, destroyed and, quote, made combat ineffective. Yes or no, was that an accurate statement? What the American military has done to the Iranian military is a historic military. Will you answer the question? Under oath, three weeks after you'd already said Iran's military was destroyed and combat ineffective, you said, quote, operational. You said, quote, Epic Fury was a historic and overwhelming victory. You said Iran's military had been rendered, quote, combat ineffective for years to come. And you stated, we had, quote, achieved every single objective. Were those accurate statements? It certainly was on behalf of the men and women in uniform a historic military victory over Iran. Mr. Secretary, you stated four months ago

that Iran's military had been rendered, quote, combat ineffective military, had been rendered, quote, combat ineffective for years to come. Has Iran's military been for the last four months combat ineffective? It's been set back not just years, but likely decades. Mr. Secretary, you stated we had, quote, achieved every single objective. Was that an accurate statement four months ago? The main objective of this was to ensure that Iran never gets a nuclear weapon. Early in the conflict on day three, Mr. Secretary, early in the conflict, day three, you said one of those core objectives was to, quote, destroy the missile threat. And as you restated on day five, to quote,

obliterate Iran's missiles and drones. Those were clearly and repeatedly stated core objectives of the campaign, which four months ago you declared had been completed victoriously with every single objective achieved. Were those objectives achieved four months ago? No one ever stated that every single missile was gone. You stated on March 8th, day nine of the war on 60 minutes, you assured the American people of Iranians surrender.

Does that remain your prediction? ultimately Iran will never have a nuclear weapon to threaten the United States of America. That has been the objective and it remains so. So just to review, you will not answer whether your statement made on the 14th day of the war that Iran's military had been, quote, destroyed and made combat ineffective was a truthful statement to the American people as you sit here and ask for tens of billions more for the The senator's time has... That a historic and effective military campaign against the largest state sponsor.

of terrorism. Won't answer the question. Hey, that would be your boss if you were still in the Marine Corps. Yeah. Who, boy, he, I feel like just a little bit of levity here. I feel like he's kind of like a puppy who's peed on the rug,

and awesome, just like rubbing his face in it a bit. Not that I condone that kind of action with a monkey, but man, and he deserved it, quite frankly. But this is the thing with him on all of this is, he has been making some bombastic statements which very much demonstrate that, I mean, he should probably own this. He does not understand the nature of this conflict at all. The Iranians very

clearly are not combat ineffective. And counting the number of boats they've sunk or tanks they've destroyed is besides the point because Iran has not gone towards or built towards or does not have a conventional military capability like the United States. They never, it's not one of their objectives. Their whole objective was to build a kind of a modern asymmetrical type of capability that sits right in the seam of the gaps in our defense, which is what we're seeing. The weakest part of our military right now is our air defense, and they are able to exploit that weakness at will, and it's highly effective. They are dictating the tempo right now. They have what we would say, the complete initiative.

And it would behoove, to pull out a military term, like I used to get lecture by my staff and COs, it would behoove the secretary to accept that because until he accepts that, you can't change it. And quite possibly the only way to change this at this point is to pull our guys out, because we do not have the munitions to defend against these missiles and these drones, nor do we really have the capabilities to do it built into our forces anymore because it was one of those things that was stripped out. during the global war on terrorism because we didn't fight an enemy in Iraq or Afghanistan.

It had a massive air capability. And as such, we moved those people elsewhere. And we were actually in the process of retooling the entire military to face more conventional threats, built around drones and hypersonics and various kinds of missile systems. But that process had just started. I used to work in this industry. They had just put the bids out to really be. up these capabilities and to bring them up to the modern day standards and had to even start a

production yet and he knew this and once again that's a failure of leadership and his insistence to focus on you know eliminating things that don't matter on the battlefield and classifying it as somehow getting rid of the Iranian military is at best disingenuous and if he truly believes that he needs to quit because he doesn't know what he's doing Jim I enjoy very much our conversation what is the name of your podcast and how can we find you and one of you up next judge uh i truly appreciate you bring me back on your show it's always great i've had a tremendous amount of respect for you for a very long time um one of my my favorite moments working on the hill was uh you coming into a hearing i set up on war powers and i it's uh it was fantastic but uh you can find me at the jim web podcast on

youtube uh anywhere podcasts are out there um it's jim web under james web underscore 16 on x but But we are up at noon today. It's noon every day over on YouTube. And I promise your listeners, it doesn't compete with your time slot. I think it's so come on over. Just check it out. We've got Daryl Cooper today. We've been doing a series on some parts of history you don't really get to see.

Right now we're talking about the Mine Wars in West Virginia, which is probably the coolest bit of history that they don't teach you in school. I love it. My family is from that part of the country. And so is Daryl's. So it's a it's a laborer love. Well, you're very articulate, and it's great having you on, and I hope you'll come back. Good luck with the podcast. Thank you for your time today.

Give my best to your dad. I will. I will. I'll pass along once again. He says hello from last time, and he did not mind that you called him my grandfather. I won't ask what your mother thought. All the best, Jim. Thank you.

I appreciate you. Thank you. A great conversation with a very, gifted and courageous young man coming up later today the end of the day the end of the week our favorite time the intelligence community roundtable today with ray mcgoverned larry johnson and joe kent at four o'clock eastern judge napal tano for judging freedom