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Andrew Weiss: Putin’s Secret Strategy and the Russia-Iran Connection

Brian Kilmeade Show / Brian Kilmeade
The Truth Network Radio
May 10, 2026 12:00 am

Andrew Weiss: Putin’s Secret Strategy and the Russia-Iran Connection

Brian Kilmeade Show / Brian Kilmeade

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May 10, 2026 12:00 am

The ongoing conflict in Ukraine has created a crisis for Vladimir Putin, with his security apparatus disaffection and demoralization. Meanwhile, Iran is receiving support from Russia, which is trying to help them kill American soldiers. The US administration's policy has given Putin confidence that he can wait out Ukraine, but the Ukrainians are determined to resist and have made significant advancements in defense technology.

COVERED TOPICS / TAGS (Click to Search)
Russia Ukraine Iran Putin Trump Middle East War
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And we canvassed the opinion of FSB, GRU, SBR, Interior Ministry, expecting to hear, oh, this treasonous act, you know, we must kill and we must put this down. In fact, we found two different responses. Number one, indifference. We don't care. this guy or the other guy, whatever.

Things are terrible here in Russia. This war is going horribly. Or enthusiasm. We'd much rather Progozhin than Putin.

So Putin has a real crisis on his hands because I'm not saying there's going to be a coup tomorrow, but what he has in the ranks, including of his security apparatus, the Siloviki, disaffection and demoralization. And any intelligence officer can tell you, when that's starting to hit, you become a leaky ship, and you become very susceptible to foreign recruitment and to, frankly, penetration, which is how the Ukrainians are going in there and blowing up Russian generals all the time, which is making Putin very paranoid about a possible coup. Andrew Weiss joins us now. Andrew, we don't really know what's going on inside Russia. But we get the sense that he's bulking up security because he knows his security is an issue, and he's losing he lost 35,000 troops last month.

I would be a little cautious about the flurry of reports. Like, there's no doubt that things are not going well on the Battlefield for Russia. But we have to be really cautious that we frankly don't have great information or insight into what's happening in the Kremlin these days. It's a black box. This is not a leaky organization.

There's very little information that sort of trickles out into the public realm. It's a security state, it's run by. guys who were hardcore KGB veterans or FSB officers, they fight with each other all the time. That's not new. And last point is they're fighting against a very formidable foe, Ukraine.

And the Ukrainians are great at getting inside the Russians' heads and making them feel miserable. And so this hubbub about whether Putin's sleeping in a bunker or whether he's too scared to have a parade on Red Square. That's just a great illustration, I think, of how the Ukrainians are masters at rattling Vladimir Putin's cage. But they are helping out the Iranians, aren't they? Yeah, that is definitely true.

I think Vladimir Putin, there's, you know, there was a report overnight in The Economist magazine that indicated that Russia has potentially been offering the Ukrainians a more advanced type of drone that we've seen be very effective on the battlefield in Ukraine.

So, but at the same time, Vladimir Putin does not want to alienate Donald Trump. He sees that Donald Trump is a mercurial person, that he can flip from one position to the other, just from hour to hour. And he thinks that he can use Donald Trump to get what he wants, which is for us to kind of force the Ukrainians to surrender and to give up their independence. I think. Putin's wrong about that.

I think he's not likely to be able to instrumentalize the White House to get what he wants, but he's not going to give that up as a possibility. Right.

So the economist pointed out that they had about 5,000, they have short-range fiber optic drones. That are tough to counter, that they would be giving to Iran. And I'll tell you what, the one thing is pretty clear. They're able to do some damage to our bases because of the satellite information the Russians were able to give. Don't you think that is a fact?

Yeah, so we've seen, I think, disturbing reports of both Russia and China providing limited support to Iran. It's something that the administration has tried to downplay. I think in a rather clumsy way, you've seen Donald Trump, Pete Hegseth, and other senior figures in the White House team keep saying, oh, it hasn't really made a big difference because we continue to be very successful on the battlefield. But the short reality is that Russia is trying to help Iran kill American soldiers. That's completely unacceptable.

And I think it's a mistake for the White House to downplay it. You know what's interesting, the president goes, well, aren't we doing that with Ukraine? The president's almost rationalizing Russia's role. Yeah, no, he's using Vladimir Putin's talking points. And then, you know, the Russians have, you know, in their, you know, clever way, have said, well, if you just stopped helping Ukraine, I'm sure we can work this out.

So, you know, the United States is helping Ukraine because it's in our interest, it's in our national interest. And, you know, that's not because it's a favor, and we're not doing it because we're cynical. You know, we're doing it because Russia invaded without any reason and has been essentially conducting a genocidal war. for more than four years. Like Americans should be angry about that.

And the United States should not be in the business of helping Russia be victorious in Ukraine. And unfortunately, this administration's policy has given Putin confidence that he can wait out Ukraine, that time's on his side, and that it's just a matter of time between the U.S. either stop supporting Ukraine, that the Europeans don't have the schlitz to help them in terms of their military requirements. And it's just fostered a sense of confidence. Among Vladimir Putin and his top advisors.

Which we know is not the case because they've already generated and engineered their own long-range missiles. They've already gotten Starlink to stop providing any service to the Russians. That allowed them to make great progress. And now they've engineered robots that have entire Russian units surrendering to them. They're not going anywhere, Ukraine.

Yeah, 100%, Brian. And I think that the administration pretty early on bought into the argument that it was just a matter of time before Ukraine was forced to surrender. We've seen that Russia has now created its own worst nightmare right on its doorstep. It's got a permanently aggrieved Ukraine that's going to be well armed and determined never to let this happen again. It's reanimated NATO and the European partners of the United States and allies to rearm.

And Russia has lost hundreds of thousands of people in a senseless war.

So Vladimir Putin is not invincible. And the president keeps saying things like Ukraine doesn't have the cards. And then every day we see things get blown up due to these, as you say, remarkable defense technological advancements that Ukraine has pioneered. And we have a lot to learn from them. And we've seen in the war in Iran that there's a lot of new technology out there on the battlefield, and we're not ready for it.

And Ukraine is the place where a lot of those innovations are being seen every day. And they're, you know, they're, they want to be our friend. They want to be a partner. Russia just doesn't fit in that category. Russia's a, you know, a longtime adversary of the United States, and there's just not a prospect for the U.S.

and Russia to suddenly become partners on the world stage, unfortunately. Yeah, it isn't. And they had every opportunity to do it, and they don't seem to understand that, or they don't want to understand that.

So let's talk about Iran. Looks like the skirmishes show me that they're not close to signing any type of deal that would be acceptable to the Trump team. I want you to hear Mike Pompeo. I think he's on the money cut 10. It wouldn't surprise me if they can figure out a way to keep their economy running for months and months.

We've seen Chairman Kim do it in North Korea. We've seen they'll put their own people in absolute poverty and protect themselves at any cost, and they'll kill people if they have to do it.

So that doesn't surprise me terribly. They're looking to outlast us, and the CIA says, as bad as things are, they could outlast us through the midterms by just holding out. Yeah, it's a similar situation that we've seen, you know, the Russians facing, which is Ukraine wins by not losing. And, you know, I hope that people look at the situation in the Middle East and are, you know, asking some tough questions. Like, what's the strategy here?

And is there, you know, a timeline and a price that's worth paying? We've been in a very difficult relationship with Iran now, you know, since the late 1970s. It's not a pushover country. And I think, you know, the administration needs to be able to explain to the American people how they got us into this mess and if they have a credible plan for getting us out. Hi, everyone.

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Well, degrading one of America's premier enemies is a good objective, degrading and destroying a regime that just killed about between 30 and 40,000 of their people. Here's General Keen on what should be next. Cut six. In my judgment, I think we've got to see reality for what it is. We should go back and execute Project Freedom, take the straight of Hormuz away from the Iranians, secure it and open it for navigation, and also at some point get some assistance in doing that.

And then we have to unleash the Israelis. They have a very comprehensive bombing campaign that they're going to conduct that deals with leadership, it deals with energy, it deals with all the weapon systems we still have to go through.

So he says you keep Carg Island as a asset, cut seven. We have an ace here up our sleeve, so to speak. It's Carg Island. And we're obviously blocking it now from any transport coming out of there. And that represents 90% of their oil resources.

So we can hold Carg Island hostage. If you're going to attack Qatar's natural gas or the Saudis or the UAE's oil fields, we're going to begin to take Carg Island away from you in terms of physical destruction. And we communicate that to them very clearly and unequivocally, what the intent is here. And he says there is an arms program in the process of getting the people some arms. What are your thoughts about that, Andrew Weiss?

Brian, I think we're hearing a repeat of the kind of magical thinking that prompted President Trump to make this. Impulsive decision to launch a war against Iran at the end of February. You know, there was a presumption in the wake of the successful abduction of Venezuelan leader Maduro that we would see Iran be very easily sort of toppled, the Iranian regime toppled. And that clearly didn't happen. And I think it's unfortunate that people are continuing to suggest that there's a silver bullet or a quick fix to this problem.

Previous presidents have all been prepared to go to work. And fight Iran, but they've also always been very cautious about the limitations of U.S. power in the region and be careful not to expose the limitations of our power. I think unfortunately the strategy that this administration is pursuing has done exactly that. It's created huge tensions between the United States and our longtime allies and partners in the region, countries like Saudi Arabia and others that are really worried that the United States is creating more problems than it's solving.

And I think this is going to be an open-ended problem, unfortunately. I don't expect it to end anytime soon, despite the continued indications from the president and others that it's just another day or two and we're going to have this thing fixed. That's just, I think, patently misleading. Yeah, I think it's not a day or two. I think maybe the ceasefire was probably a mistake.

I think with the thing that's different, I think, is they've already eliminated about between 40 and 80. It's hard to get a number of their leaders. And the other thing is the Israelis are involved, and their intelligence has shown over the last three years is impeccable. And I think that their air power can handle it, and we could reopen the strait and then bring them to the table. I think they'd be much more appliable to something that we can deal with.

Yeah, it just comes back to the we're in a pain contest, and I'm not sure that the United States can absorb the kind of pain that Iran seems to be willing to dish out, as well as the impact it's having on the global economy by keeping the strait closed. What do you see next with Cuba? You know, I think the administration has done a lot of work to try to rattle longtime foes of the United States and to suggest that the U.S. is prepared to unleash all the attributes of our national power against them. There was a period in the first year of the administration, sort of culminating in the operation to seize Maduro, where I think all of that was creating a lot of worry in places like Havana.

But the results of the Iran war, I think, now are sort of making countries that breathe a sigh of relief that the United States might not be able to push on so many fronts at the same time. And that it really is, there's a real risk of overextension. And that's been something, again, that just gets back to the sort of spur of the moment, seat of the pants approach that this administration has adopted in its foreign policy. And then, frankly, the process of having an administration where the senior Most advisors see themselves as being limited to providing options to the president as opposed to providing candid advice and disagreeing with him and sort of restraining him when they think he's getting ahead of where U.S. capabilities and ambitions actually end up.

You know, it's interesting.

Sort of inability to match means and ends. But if you believe the report, Kane was providing options, but also said, you know, this is going to be tough. And vice president. The Vice President wasn't aboard, and I don't think he even denies that he was aboard on going after Iran, where it looks like Secretary of Defense Pete Hagseth was, as well as Cooper, thought he had a good plan for that, as did almost every CENTCOM commander for the last 40 years.

So that is the push and pull you expect on an effective administration, isn't it? Yeah, I'm not so sure that describes how these meetings are going. I think the president has really been, in this administration, unlike the first time he was at the White House, he really is resistant to people who don't agree with him. And I think the incentive structure of how to stay on the president's good side is to be as agreeable and supportive as possible. And we've seen him basically staff senior positions with people who either far less experience or far less political stature than he did the first time around.

I had people who really didn't like him the first time around. I think I liked General Kelly, but he was not a Trump fan, and he was his chief of staff. And the first Secretary of Defense. Not a fan.

Well, I mean, it's up to you to compare General Mattis and Pete Hagsdeth in terms of experience and the caliber of their ability to be serious advisers to the President. It seems to be pretty stark. Yeah, Mattis had much more experience. I think that also, you know, just Mattis was not on board. I think the President did a better job staffing with people that understand what he wanted them to do.

And he does get pushback. And, you know, even though he doesn't love, but he made it clear with J.D. Vance, made it clear in the meeting this could be tough. And he did not want to do Maduro. Either did J.D.

Vance. Yeah, I mean, these are tough calls. And I think that, you know, anytime, you know, President of the United States is, you know, is putting our men and women in harm's way, like that's that's the weightiest responsibility that any, you know, commander-in-chief can have. And, you know, the United States is not, you know, we're not a soda machine where we simply just push a button and things happen around the world. And I think that, as I said, the first year of this administration's tenure sort of gave, I think, a degree of, fostered a degree of overconfidence about the ability to solve tough problems overnight.

And, you know, Iran is one of the toughest problems any president has ever faced. And he's certainly addressing it. Andrew Weiss, thanks so much.

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