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Oct. 13, 2025 - Judging Freedom - Judge Andrew Napolitano
32:08
COL. Douglas Macgregor : Gaza a Sideshow; Iran the Main Event.
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Hi everyone, Judge Andrew Napolitano here for Judging Freedom.
Today is Monday, October 13th, 2025.
Colonel Douglas McGregor will be with us in a moment on Gaza and Iran.
Is peace in one related to war in the other?
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And now is the time.
Colonel McGregor, thank you for coming on the show today.
And I know it's not your usual time or date, and I truly appreciate your accommodating my schedule.
What are your thoughts, Colonel, on the events in Israel today?
I must say that I probably more than many.
I'm skeptical of all of it.
Obviously, everybody hopes for an end to the tragedy in Gaza and an end to this uh Israel versus the whole Islamic world.
But I just am unconvinced that we're going to get much beyond this initial phase of uh returning hostages.
The the remaining living hostages that uh Hamas has, along with remains, and of course uh I think it's roughly 1,200 Palestinian prisoners that are held by the Israelis.
Beyond that, I just I just have very little confidence that this kind of peace could be sustained.
And I still think that uh the war with Iran looms over the horizon.
What what undermines your confidence?
Is it the right wing pressure from within his government on Prime Minister Netanyahu?
Is it his failure to have defeated uh Himas Hamas?
Is it his recognition of the destruction he's caused to Israeli society that in his own way of thinking can only be resolved with more, can only be united with more war.
You know, I suppose it's it could be all of those factors.
I also think this is something that President Trump both wanted and felt that he needed.
President Trump has been frustrated because he hasn't been able to publicly take uh credit for some sort of peace arrangement in the Middle East.
I think he very much wants a settlement.
Having said that, he now has the optics of a settlement.
And frankly, for him, that may be enough.
Uh, he's very focused on optics, on appearances.
Right.
You saw him on the stage in front of the giant American flag, all of George Patton in the movie.
I I think he's he's very delighted with that, but I would point out that in the final analysis, he is not a completely free agent.
I think he's still a prisoner of his donors.
And his wealthiest and most important donors are those associated with Israel and its interests.
I think they wanted something, but I don't think they've given up on the Greater Israel Project at all.
So I think this is a pause.
How long will it last is anybody's guess?
Well, the Israelis are committed, A, to greater Israel, and B to eradicating the Palestinians from the Gaza Strip and the West Bank.
I mean, that that's that's in their genetic makeup, or at least this government has committed them to that.
Well, I think the Israeli population agrees with you, Judge.
I think at least 80% of them are absolutely supportive of those goals.
So this again looks like a pause to me as opposed to some sort of permanent outcome.
What happens when the IDF uh resumes bombing Gaza, which could happen next week.
Yeah, I my impression is that uh once all the hostages are returned, there will probably be some uh small period of pacification or something resembling peace, but then the shooting will resume.
And there are so many other actors involved in this thing right now.
The Israelis have some proxy forces that are Arabs, supposedly with some connection back to Syria and ISIS.
Then you still have Hamas that remains active and supportive.
I I just don't see how this mix of uh volatile participants can avoid colliding with each other.
So I think you're right.
I think at some point the bombing will resume.
Now the question is what happens with Iran, and I know that uh certainly President uh Netanyahu was able to talk briefly on the phone with uh President uh Putin and supposedly expressed the view that Israel doesn't want a war with Iran.
Well, I think the Iranians have heard that before.
I'm not sure that's going to change anybody's uh readiness to fight in Iran.
So I I'm still I'm just skeptical by nature of the whole business.
This has been tried before, it doesn't work.
I want to ask you about Iran in a minute, but before we do, I want your comments on some of the more extreme things the president uh said today.
Um I wonder if he thinks that Netanyahu is guilty of crimes and for that reason needs a pardon.
Uh, Chris number 12.
Hey, I have an idea.
Mr. President, why don't you give him a pardon?
Come on.
By the way, there was not in the speech as you probably know, but I happen to like this gentleman right over here, and it just seems to make so much sense.
You know, whether we like it or not, this has been one of the greatest wartime presidents.
This is what been one of the greatest wartime presidents, and cigars and champagne, who the hell cares about.
First of all, he's referring to the prime minister of Israel as the president.
Secondly, to say that he is engaged in behavior that can be characterized as great, is truly demented, in my view, in light of what Netanyahu has done.
He has caused the entire world to question the moral basis of the Zionist experiment.
Well, isn't that uh testimony to the extent to which uh President Trump is out of touch with reality?
Yes.
I mean, he's addressing his donors right there.
His donors are watching.
These are the people that have paid for the White House, as well as control of Congress.
Uh and Netanyahu is their hero.
They all sympathize with the the goals that we stated earlier.
I I don't think anybody should be surprised by this.
Also keep something else in mind.
You know, President Trump is somebody who interacts with audiences, and if he feels the audience likes something, he struck a chord, then he elaborates.
So if the audience hadn't clapped as vigorously as they did uh earlier, he might not have said what he did.
I'm not sure that a great deal is thought out in advance.
He said, Well, this wasn't in the original speech, As you know.
I think he's being quite honest there.
This is an impulse-driven personality.
And I don't think he carefully considered the consequences or impact of his words.
At one point, he uh praised the Mossad's wealthiest asset and recounted her inability to say which country she loves more.
Number 11, Chris.
Got 60 billion in the bank, 60 billion.
And she loves, and she I think she said no more.
And she loves Israel, but she loves it, and they would come in, and her husband was a very aggressive man, but I loved him.
He was a very aggressive, very supportive of me.
And uh he'd call up, uh, can I come over and see you?
I say, Sheldon, I'm the president of the United States.
It doesn't work that way.
He'd come in with the.
But they uh were very responsible for so much, including getting me thinking about Golan Heights, which is probably one of the greatest things to ever happen.
Miriam, stand up, please.
She really is.
I mean, she loves this country.
She loves this country.
Her and her husband are so incredible.
We miss him so dearly.
But I actually asked her, I'm gonna get her in trouble with this, but I actually asked her once I said, so Miriam, I know you love Israel.
What do you love more?
The United States or Israel?
She refused to answer.
That means, that might mean Israel, I must say.
But it was reprehensible that he would be joking about that, that he would recount it, that he would tell the world her supposed wealth, which is an extraordinary number, but nobody's business.
Well, I remember that uh Miriam's husband was the one who called Donald Trump and begged him to talk to John Bolton, urged him to consider John Bolton for the job as national security advisor.
And up until that point, uh President Trump had refused to meet with a man.
He didn't like Bolton, didn't like anything about him and didn't want him around.
But uh Adison said, please, Donald, please talk to him.
He's a good man.
Well, that's how we got John Bolton.
So I think I think we have to remember if that's how you got John Bolton, that's how you got the war in Israel.
That's how you're going to get everything else.
Is there a connection?
Can you draw a line between the ceasefire in Gaza and the Israeli slash US plans to attack Iran?
You know, to do something like that, I would have to be uh on the inside of the decision-making process.
I'd have to have intimate knowledge of what is being discussed in the joint staff and in the chairman's office, and I just don't.
So if I were to draw a line from one to the other, I could say, well, perhaps a certain amount of uh peace in Gaza is necessary while uh Israel presses ahead with its plans to attack Iran.
I don't know.
Uh one of the things that has always worked in Israel's favor has been the inability of the various uh states in the region to unify against them.
Uh, no one has been willing to do that.
And so Iran is uh really the the lone ranger in the region.
Iran has stood up to Israel, has made it clear it won't submit and is quite capable of fighting Israel.
Everyone else has sort of stood around and shivered in fear of the United States if they were to lift a finger against Israel.
I I don't know.
It's possible.
Uh I am very, very skeptical that anything that uh Mr. Netanyahu Yahoo says is true, at least uh insofar as uh saying uh we don't want war with Iran.
I think he might have said we don't want it right now.
That I might believe, but I I don't see how they get past uh the war with Iran.
Then again, I don't know the level of damage inside Israel.
And again, Israel is uh effectively what the 51st state of the United States now.
So as long as we're sustaining them and and keeping them afloat economically.
They can continue in this kind of uh Israeli Disney world where we will do whatever they want and they can do whatever they like.
I want to talk to you about tomahawks.
Not not the stake, but the missiles.
You and I had some nice Texas uh beef the other day in the great city of Dallas.
Chris, uh well, watch this, Colonel, please.
Cut number nine.
We talked about weapons, and the weapons are sent to NATO, and NATO then sends us a check.
They paid for info, and uh they would need more weapons, and we're looking into doing that.
We we hope we're gonna be able to provide them.
They'd like to have tomahawks that's a step up.
They'd like to have tomahawks.
We talked about that.
And so uh so we'll see.
Well, I don't know.
I may I might have to speak to Russia, to be honest with you about tomahawks.
Do they want to have tomahawks going in their direction?
I don't think so.
I think I might speak to Russia about that, in all fairness.
I told that to President Zelensky because tomahawks are a new step of aggression.
Are you saying that you will speak to Putin first about Tomahawk?
Talk to him.
I might say, look, if this war's not going to get settled, I'm gonna send them tomahawks.
I may said that.
If the war is not settled, that we may very well, we may not, but we may do it.
I think it's appropriate to bring up uh Lukashenko of Belarus, who often uh expresses what President Putin of Russia thinks, said they think that this is a bluff.
But can you tell us what we need to know about tomahawks?
How significant are they, how many are available, what damage can they do?
Are the Russians afraid of them?
Why would Trump be taunting them with these?
Uh well, the first thing before we go into the details about the Tomahawk, which are which are worthwhile mentioning, uh, we need to sort of note this condescending, condescending, insulting speech towards Russia.
I mean, President Trump is acting as though he's the father of two disgruntled disgruntled children, and uh he's uh admonishing one of them to be good and do what he's told.
This sort of thing does not help us with Russia at all.
It really infuriates uh the Russian population.
I'm sure it antagonizes and disappoints President Putin.
And even though I'm I'm well aware of uh President Lukashenko's remarks, and I think that he's expressing a particular viewpoint that that I think to some extent is shared by President Putin.
I think President Putin and uh the Russian leadership have just about had enough of uh Mr. Trump's uh sort of uh bloviation and uh uh silly remarks to be blunt.
Now, having said that, the tomahawk is not some sort of miracle weapon that the Russians should be death desperately afraid of.
I don't think that's the issue.
It has a 1500 mile uh range, uh, but that depends on the variant of the tomahawk we're talking about.
There's a tomahawk you fire from a bomber, there's a tomahawk that is launched from a submarine, there's a tomahawk that could be launched from a destroyer, an ages class destroyer.
Then there is a ground-based tomahawk uh that the army developed.
I don't know how many of them there are.
I don't even know what the tomahawk inventory is, but from personal experience back in 1998-99, uh, the inventory is not that large.
And if you think you're going to launch tomahawks in one theater before you do, there is usually cross-leveling between uh regional unified commands to make sure the unified command that's about to use tomahawks actually has enough of them.
I imagine that we are probably low in terms of our inventory of tomahawks, especially new ones.
We have a lot of old ones sitting around with questionable reliability.
Perhaps we'll throw those into the mix.
But again, what can we give to the Ukrainians?
And the logical answer is well, we could give them the ground launched version, which the army has, but that's going to take uh American mission planning and execution.
That means you're gonna have to have American soldiers or at least contractors on the ground with it.
Uh, it has a unique warhead.
I don't know how many of those warheads are on uh online and ready for use.
Then there is the 40-foot container version of the tomahawk.
Uh That could be mounted on a barge and then uh launched out of this uh box the way you see uh missiles launched from ships.
I guess you could put it on the uh on the track track bed of uh of a rail car.
I don't know.
I mean, this depends on on how far along we are, and again, how many of these things do we have?
Now, having said that, this is not a missile that flies fast enough to avoid being detected on radar.
Tomahawk missiles were downed during the Kosovo air campaign by the Serbs.
They shot them down.
Now they had an advantage because you were operating through Albania and through the mountains, and there were only so many places the Tomahawks could penetrate.
Whereas in eastern Europe, you've got a much wider range, uh, 1,100 miles to choose from in terms of where you might launch from.
But I don't think the Russians are that concerned about the missile per se.
However, given its range, if even one or two or three of these got through and absolutely hit targets in civilian neighborhoods, which is what the Ukrainians like to target.
They they've shot weapons and uh various missile systems, rockets, and conventional munitions into uh civilian neighborhoods.
And if that were to happen, and a large number of Russians were injured or killed, I think the pressure on Mr. Putin to respond would be enormous.
And I'm not sure how he would respond because everybody knows this is an American weapon.
Uh people will know that it could not be fired without American military personnel or contract personnel on the ground operating it.
I think the temptation to launch large numbers of Oreshniks that could strike targets all the way from Lithuania to Romania would be enormous.
I mean, people in Russia, and I don't think Americans have any idea what this is like, are really fed up, fed up by the whole thing.
This is analogous to a situation where you know the Russians or the Chinese or somebody put similar missiles, cruise missiles into Mexico, put them into the hands of the drug cartels, and then said, do your worst and walked away.
Uh, what would we do under those circumstances?
Would we simply blame the cartels?
No.
I think we would go after Russian or Chinese targets.
My concern is that would happen here in eastern Europe if President Trump decides to press ahead with it on the grounds that the Russians have failed to come around and stop the war per direction.
Colonel, are they nuclear capable?
You know, I don't think any of the ones that we have right now in the in the theater are.
There may be uh nuclear-capable tomahawks, but the ones that would be used, no, I don't think so.
I think they're gonna all they would all have conventional warheads.
Back to uh Iran, are you still of the view that when they're ready, the Israelis and the Americans will attack?
Uh Alistair Crook is of that view, and he uh believes it'll be sooner rather than later because of atmospheric conditions uh that begin around Christmas time.
Well, I don't know about the atmospheric conditions uh that may they may play a more important role than I think.
Uh I I simply think the Israelis are gonna have to make a decision.
Fisher cut bait, and if they cut bait, that means they've given up.
And you know, President Trump said under no circumstances can the Iranians enrich any uranium.
Well, that's not going to happen.
That's obvious.
The Iranians have already made that abundantly clear.
Then he says they may never have nuclear weapons.
Well, the Iranians say they have none.
And there's a lot of evidence to support the truth of that statement.
But that doesn't change the Israeli obsession with Iran.
And Israel feels that Iran is an existential threat.
I don't see that that changes with the potential for peace in Gaza at all.
Uh, one last thing about um tomahawks, if I may.
Here's uh uh very serious uh President Putin uh Talking about it quite recently.
Chris, cut number five.
It's dangerous.
As for the Tomahawks, it's a powerful arm.
Perhaps not the most modernized, but it's powerful.
Poses serious threat.
This will not change in any way the balance of powers on the battlefield, the fundamental issues of the armed forces of Ukraine.
No matter how many UAVs they get.
And no matter how many lines they create with those UAVs, without the personnel, there will be no one to lead those battles.
They have to change the tactics.
Will this pose damage to our relations?
Where we see light at the end of the tunnel, of course.
Of course.
Without direct involvement of the U.S. officers is impossible.
Which means a brand new stage of escalation, even between in the relations between Russia and the U.S. What if anything was gained by the Anchorage Alaska meeting between Presidents Trump and Putin?
I think initially there was the view, and I think the Russians held this as well, that the fact that President Putin and his team met with uh President Trump and his team was a good thing.
I think we all saw that as a as a positive development.
The problem is that it was a uh dialogue of the death.
In other words, we didn't listen to anything they said.
In fact, I'm not even sure we understood what they were telling us, because they didn't tell us anything that we hadn't heard before.
But then what's even worse is that we didn't show up with a counter proposal.
We hadn't done any homework.
We didn't walk in and say, well, we've studied your position.
Uh we can agree with these five points, but there are three other points uh where we we're looking for some flexibility.
At which point in time the question from the Russian side would have been well, tell us what these points are and we'll talk about them.
That never happened.
So at this point, we have to say it was irrelevant.
It was another uh exercise in optics by President Trump.
He put on a great show.
Uh is sort of he treats all these things as though he's going to the Al Smith dinner in New York City, cracking jokes and making wisecracks.
Uh that's what he did in the Knesset, and that's the kind of thing he likes to do.
Understand that, but this is not what you do in international relations when you're talking about issues of life or death.
And that's what we're talking about in the Middle East.
That's what we're talking about in Ukraine.
And I'm told that very recently, I keep I'm trying to track this down, but that he made a statement that we would go in on the ground in Venezuela to quote unquote attack drug cartels.
Not sure I entirely understand what that means, but that seems a rather strange thing to mention in the midst of everything else.
Wow, I don't think Congress has declared war in Venezuela, but maybe that wouldn't stop him.
I mean, he's already been blowing these boats out of the water.
And you talk about visuals, he has ordered the Secretary of Defense, who calls himself the Secretary of War, to reveal uh video footage of the boats being uh obliterated.
Senator uh Tim Kane, I don't agree with Senator Kane on much, but he's hot on this.
He's on the Senate Intelligence Committee, so I assume he knows what he's talking about.
Uh this is from three days ago, Chris.
Cut number 14.
I think there's a significant likelihood that in one of these first four strikes already that it was a mistake.
The Coast Guard stats show one in four ships that the Coast Guard interdicts for suspicion of drug activity has no drugs on it.
Oh my god.
So there's already a one in four chance that you're gonna stop somebody, it's gonna turn out that they don't have drugs.
So due process, laws of war, not letting this president or any president be able to put our troops in harm's way to wage war without having that debate and vote by Congress.
Donald Trump is saying I've created my own secret list of groups that I'm gonna target in the Caribbean.
Can we see the list?
No.
So a secret list that he's created, neither Congress nor the American public is seeing It and he's taking strikes on now four and he's threatening more.
To me, the thought of a land invasion of another country, no matter the goal without authorization from the Congress is a constitutional anathema.
Oh, listen, I agree 100%.
The problem is that when did we debate the wisdom of going into Iraq in 2003?
Right.
We did have uh, I don't know if we call it a debate as much as a series of discussions and hearings before 1991.
Uh, but nevertheless, uh we just haven't had much in the way of debates on anything, Judge, as you know.
That's a huge, hugely frustrating aspect of the whole thing.
I mean, why bother having a Congress if you're not going to debate any of these issues?
But there's something else that Americans need to understand, and no one is talking about it.
Venezuela is, I don't want to say it's brittle, but it's fragile.
And whether you like Maduro or not, he's held the country together.
Inevitably, we seem to be interested in removing him and replacing him with this new Nobel Prize winner.
Why she got the prize is a mystery to me, but nevertheless, she got it, and now they're talking about putting her in.
The problem is that I don't think she can hold the country together.
There's the other aspect of this.
Supposedly there were offers made uh in other channels back and forth from Venezuela to Washington, uh, that essentially would have given us uh access to their uh oil and gas uh reserves.
It could have brought us in to do a lot of drilling, which they desperately need, could have met our requirements, and apparently we categorically refused all those overtures.
And then finally, we underestimate the extent to which this entire Latin American continent along with Central America could blow up in our faces.
I I don't understand why no one is aware that marching into a place like Venezuela, even if you say you're going to do or conduct surgical operations.
I'm I imagine that's the next thing they'll talk about, uh, could infuriate uh millions of people all over Central America as it is.
We're already listening to people in a drug cartels down in uh Mexico threatening to kill Americans wherever they find them.
Uh there is a great deal of latent hate and hating hate, animosity, and antipathy for us.
This is not going to help our case down there.
In other words, I just don't see any benefit to it.
Right, there isn't even a debate.
There, and I, you know, like you, I'm not a cane fan, but he's effectively correct.
He's on another uh campaign, which is to, and on this I fully agree with him, rescind the authorizations for use of military force from from the George W. Bush era.
Oh, absolutely.
Because presidents, Barack Obama did this, Donald Trump did this, will rely on the open-ended language in these.
Here he is, again in the same interview, but now talking about these AUMFs.
Number 14, Chris.
The Iraq War was declared by Congress in 2002, but Congress often declares a war and then just leaves the authorization on the books.
And then a future president, like I want to do something in the Middle East.
Oh, you know what?
Here's this authorization out there.
I can say it's justified by that, and that Congress authorized it.
And as far as I know, it's gonna be the first time in the history of the United States that Congress actually repealed a war authorization that we passed, which means that a president can't then go grab it and use it for a mischievous purpose.
Well, the authorization for the use of military force not only confers essentially limitless freedom of maneuver on the White House to attack when and where they care to and attack whomever they don't like, it's worse than that.
It legitimates huge numbers of additional uh flag officer billets, in other words, more admirals and more generals and more headquarters.
And this is something, of course, that uh the Department of Defense now, the Department of War loves.
And that was written into the original authorization for the use of military force.
There are other provisions in there that allow for expenditures.
The bottom line is that the authorization for the use of military force should go away.
Absolutely, as soon as possible.
But whenever anybody brought that up, uh whether it was uh the Obama administration or uh President Trump's first administration, everybody sort of shrugged and said, Well, there's no real interest in doing that.
Well, if you look at some of the provisions and the freedom of action that it grants, I guess that's uh that makes sense, but it's not in the interest of the American people.
Colonel McGregor, thank you very much, my dear friend.
A great, a great, fascinating conversation, which uh covered all of the hot topics of the day and the week.
And uh truly appreciate it.
Thank you for accommodating my schedule, my dear friend.
Well, listen, you have a great trip and come back safely to us.
Thank you.
Thank you, Colonel.
See you soon.
Bye bye.
Bye bye.
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