What Trump Wants in Cuba

Summary

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Podcast Summary: Big Take – "What Trump Wants in Cuba"

Date: March 24, 2026
Host: Sarah Holder (Bloomberg News)
Guests: Jim Wiss (Bloomberg Reporter on Cuba), Eric Martin (Bloomberg State Department and Foreign Policy Reporter)

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Overview

This episode of Bloomberg's "The Big Take" explores the sharply escalating U.S. pressure on Cuba during President Donald Trump's second term. The focus is on the American strategy—political, economic, and potentially military—aimed at triggering profound change in Cuba's government. The discussion also analyzes the key role of Secretary of State Marco Rubio, the impacts on everyday Cubans, reactions from the Cuban diaspora, and what might come next as both countries reach a possible inflection point.

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Key Discussion Points & Insights

1. Escalation of U.S. Policy Toward Cuba

• President Trump’s attention to Cuba has intensified in his second term.
• The appointment of Marco Rubio (son of Cuban immigrants, Miami political base) as Secretary of State signaled a renewed hardline posture. ([02:15])
  • Quote: “The naming of Marco Rubio...was a strong signal that the communist governments in the Western Hemisphere were going to be a big focus of attention for the administration right out of the gate.” – Eric Martin ([02:15])
• Rubio led the push to re-designate Cuba as a state sponsor of terrorism, reversing Obama-era thawing efforts. ([02:40])

2. The Oil Blockade and Knock-On Effects

• After the US ousted Venezuelan President Nicolas Maduro in January, a key source of Cuban oil was severed.
• Imposed American oil blockade has devastated Cuba’s energy and economic sectors, causing week-long blackouts and severe hardship. ([03:11], [03:30])
  • Quote: “Some nights the entire island goes dark.” – Sarah Holder ([03:30])

3. Cuba at a Breaking Point

• Cuba is experiencing its worst crisis since the "special period" following the fall of the Soviet Union. The government has acknowledged being unable to deliver food and aid due to lack of fuel. ([04:09], [04:47], [08:04])
  • Quote: “It’s a huge moment... 67 years and it's looking really unclear if this one-party system is going to survive the year.” – Jim Wiss ([04:09])
  • Quote: “Industry is grinding to a halt, and resorts... have had to shut down because there’s not enough fuel. ...Hunger is real.” – Jim Wiss ([08:04])

4. The Venezuela-Cuba Relationship: Critical Context

• Historical context: Venezuela became Cuba's lifeline after the Soviet Union’s collapse, sending oil in exchange for Cuban expertise and labor.
• The U.S. cutoff of Venezuelan oil to Cuba—and threats against other suppliers like Mexico—has left Cuba isolated. ([05:25], [07:03])

5. Popular Dissent and Government Survival

• Unconfirmed reports of deaths in hospitals, more visible protests including attacks on Communist Party offices, and general dissatisfaction toward both governments. ([09:02])
• Outright demonstrations are banned, but discontent is surfacing.
  • Quote: “There’s a lot of dissatisfaction on the street, some of it aimed at Washington, some of it aimed at the local authorities.” – Jim Wiss ([09:02])

6. U.S. Goals: Dominance and Democratic Change

• The Trump administration’s national security strategy, released in December, focuses on reasserting U.S. dominance in the Western Hemisphere and preventing influence from nations like China.
• Nostalgia and strategic interest among the Cuban-American exile community in Florida further shape policy. ([09:49])
  • Quote: “This is an administration that... is very focused on asserting US preeminence and dominance in the Western Hemisphere.” – Eric Martin ([09:49])

7. Diaspora and Expatriate Reactions

• The Cuban diaspora shows interest in investing and changing Cuba, especially with recent Cuban legislation allowing exiles to participate in the economy.
• However, skepticism abounds due to Cuban government history of expropriation and complicated legal realities. ([11:08], [17:38])
  • Quote: “There’s a lot of skepticism in the exile community about putting money into Cuba... this is not nearly enough for what people need to see.” – Eric Martin ([17:38])

8. Cuban Government’s Response

• Cuban President Miguel Díaz-Canel has publicly acknowledged U.S. actions are hurting the country; describes U.S policies as "collective punishment."
• Simultaneously, the government insists it will not negotiate over who leads Cuba, maintaining a tone of defiance. ([12:13])
  • Quote: “They keep saying that... we’re not willing to discuss who leads our country.” – Jim Wiss ([12:13])

9. Prospects for Diplomacy, Intervention, or Economic Takeover

• U.S. and Cuban officials are engaged in talks. The Trump administration reportedly seeks the removal of Díaz-Canel, favoring Raul Castro's grandson ("Raulito/El Congrejo") as a possible leader more open to compromise and markets. ([15:42])
• U.S. strategy includes fostering Cuba’s private sector to trigger political opening, reminiscent of Gorbachev-era reforms in the Soviet Union. ([15:42])
  • Quote: “The US is looking to use economic pressure... to foster this private sector, which they see as leading to a political opening in Cuba.” – Eric Martin ([15:42])
• The administration weighs three options:
  • Diplomacy/deal-making (ongoing),
  • Military action ("friendly takeover" rhetoric, but no preparations observed yet),
  • Economic pressure to make Cuba dependent on the U.S. and force political changes.
• Much depends on the outcome of current U.S. involvement in Iran; a resolution there may shift more focus to Cuba. ([19:04], [20:11])
  • Quote: “He’s repeatedly said Cuba would be dealt with after Iran.” – Eric Martin ([20:11])

10. Historic Stakes and Latin American Perceptions

• Any U.S.-enforced change in Cuba would have massive historical significance after decades of failed U.S. efforts.
  • Quote: “Ever since Kennedy, successive U.S. Presidents have been trying to... force a change, negotiate a change... It’s an incredible story of kind of political survival in Cuba... if Trump was the one to do it, that would be incredibly significant.” – Jim Wiss ([21:15])
• The collapse of Cuba’s one-party system would reshape regional politics and fuel leftwing nostalgia throughout Latin America.

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Notable Quotes & Memorable Moments (with Timestamps)

• “Taking Cuba in some form. Yeah.” – Jim Wiss ([03:34])
• "Some nights the entire island goes dark." – Sarah Holder ([03:30])
• “Industry is grinding to a halt, and resorts... have had to shut down because there’s not enough fuel. ...Hunger is real.” – Jim Wiss ([08:04])
• "Ever since Kennedy, successive U.S. presidents have been trying to either force a change, negotiate a change... And it’s never happened." – Jim Wiss ([21:15])
• “He’s repeatedly said Cuba would be dealt with after Iran.” – Eric Martin ([20:11])

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Key Timestamps

• 01:46 – Episode content begins, setting stage with Trump’s renewed interest in Cuba
• 02:15 – Analysis of Marco Rubio’s impact as Secretary of State
• 03:11 – US-mandated oil blockade, economic and social impacts described
• 05:25 – Deep dive into Cuba-Venezuela alliance and its breakdown
• 08:04 – Humanitarian impacts: blackouts, hunger, hospital crises
• 09:49 – U.S. strategy: Western Hemisphere dominance, Florida exiles' influence
• 12:13 – Cuban government response: public pain, private intransigence
• 15:42 – Current state of diplomacy: who’s negotiating, what’s at stake
• 17:38 – Cuban-American investment skepticism
• 18:31 – Military intervention as a possibility, administration’s signals
• 20:11 – Trump’s sequencing: Iran first, then Cuba
• 21:15 – Historical significance and regional implications

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Conclusion

This episode paints a picture of unprecedented U.S. pressure on Cuba, intersecting humanitarian crisis, and the real possibility of regime change under President Trump’s administration. The voices of Bloomberg’s foreign policy experts capture both the human impact on Cuba’s population and the political ambition animating American strategy. The collapse or transformation of Cuba’s government under pressure from Washington would leave lasting ripples across Latin America and American political history.

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Transcript

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[Sarah Holder (Bloomberg News Host)]

President Donald Trump has been talking more and more about Cuba.

[Jim Wiss (Bloomberg Reporter on Cuba)]

You know, all my life I've been hearing about the United States and Cuba. When will the United States do it? But I do believe I'll be the honor of having the honor of taking Cuba.

[Sarah Holder (Bloomberg News Host)]

Bloomberg's State Department and foreign policy reporter Eric Martin says Trump's interest in the island nation has been building in his second term. One of the first signs was his pick for secretary of state.

[Eric Martin (Bloomberg State Department and Foreign Policy Reporter)]

The naming of Marco Rubio, senator from Florida, the son of Cuban immigrants to the US Having grown up in this Miami exile community and that being his political base as the nominee for secretary of state, was a strong signal that the communist governments in the Western Hemisphere were going to be a big focus of attention for the administration right out of the gate.

[Jim Wiss (Bloomberg Reporter on Cuba)]

Under the new Trump administration, they put Cuba back on the state sponsor of terrorism list.

[Sarah Holder (Bloomberg News Host)]

Jim Wiss covers Cuba and the Caribbean for Bloomberg.

[Jim Wiss (Bloomberg Reporter on Cuba)]

And so that really kind of set the stage for everything kind of going forward.

[Sarah Holder (Bloomberg News Host)]

And just over a year into Trump's second term, his Administration's hard line stance and its rhetoric has only picked up. After the US Captured Venezuelan President Nicolas Maduro, Rubio sent a warning to Cuba in a press conference.

[Jim Wiss (Bloomberg Reporter on Cuba)]

Yeah, look, if I lived in Havana

[Eric Martin (Bloomberg State Department and Foreign Policy Reporter)]

and I was in the government, I'd

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be concerned at least a little bit.

[Sarah Holder (Bloomberg News Host)]

Then the US Imposed an oil blockade of the island, which has crippled its economy and energy sectors.

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Now, since the US Ousted Venezuelan leader Nicolas Maduro in January, Cuba's main supplier of oil has been choked off, triggering weeks of blackouts. Some nights the entire island goes dark.

[Sarah Holder (Bloomberg News Host)]

And just last week, Trump started talking about taking Cuba.

[Jim Wiss (Bloomberg Reporter on Cuba)]

That'd be good. That's a big honor, taking Cuba. Taking Cuba in some form. Yeah.

[Sarah Holder (Bloomberg News Host)]

The U.S. s approach to Cuba address, especially over the past year, has had significant impacts for people on the ground.

[Jim Wiss (Bloomberg Reporter on Cuba)]

The United nations has basically said that the government can no longer deliver food and aid to kind of the most vulnerable parts of the population simply because they don't have enough gasoline to put in the cars.

[Sarah Holder (Bloomberg News Host)]

So it's dire and it's all building, Jim and Eric say, to an inflection point, one that could alter the course of Cuba's history and the legacy of the Trump administration forever.

[Jim Wiss (Bloomberg Reporter on Cuba)]

I mean, it's a huge moment. I mean, arguably everything's at stake right now for the government. They've been in power 67 years and it's looking really unclear if this one party system is going to survive the year.

[Eric Martin (Bloomberg State Department and Foreign Policy Reporter)]

Quite frankly, we've seen a dozen presidents come and go, unable to change the government in Cuba. So if the Trump administration and Secretary of State Marco Rubio are able to bring about that change, it would be a huge legacy issue for them and a historic change that they would be implementing and catalyzing in Cuba.

[Sarah Holder (Bloomberg News Host)]

I'm Sarah Holder and this is the big take from Bloomberg News today on the show Cuba at a turning point. Why the US has been ramping up pressure on the nation and what could come next. When the US Carried out a military operation to capture former Venezuelan President Nicolas Maduro in January, it was a pivotal moment for another country, too. Cuba. The relationship between Venezuela and Cuba is a key piece of context for understanding what's happening today. Here's Bloomberg's Jim.

[Jim Wiss (Bloomberg Reporter on Cuba)]

So you know, when Hugo Chavez took power in Venezuela, he immediately or very soon after taking power saw enfidel, kind of a mentor and kind of a godfather. And of course, the two of them became kind of the leaders of what was known as 21st century socialism, Latin America. At the root of that relationship was Venezuela's support for Cuba Cuba was coming out of what was known as the special period after the fall of the Soviet Union, and they lost their Soviet backing. They went through a true economic crisis, and Venezuela stepped in as kind of its savior. And so this relationship developed where Venezuela was sending hundreds of thousands of barrels of oil a day to Cuba, and Cuba was paying for it by sending teachers, security personnel, engineers, and people of that sort. And so there was this barter system in place that worked very well for both sides until it didn't. And, you know, even as the Venezuelan economy started to fail, they still continued to support Cuba. And so Cuba, at the end of the day, was kind of very, very overly dependent on their Venezuelan patrons. And when Trump essentially cut that off cold on January 3rd, you know, the effects have been very, very evident.

[Eric Martin (Bloomberg State Department and Foreign Policy Reporter)]

Protesting the latest power cut on the

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streets of Havana after Cuba's entire electricity

[Sarah Holder (Bloomberg News Host)]

grid collapsed last night.

[Jim Wiss (Bloomberg Reporter on Cuba)]

The power cut comes as campaigners delivering humanitarian aid have started arriving in the country as part of efforts to mitigate the effects of Washington's blockade.

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In a nation used to hardship, Cubans

[Jim Wiss (Bloomberg Reporter on Cuba)]

say the situation has never been worse. The president of Cuba, Miguel Diaz Canel, has basically said they haven't had a major oil delivery in over three months, basically, essentially since the US Incursion into Venezuela. And the US has basically threatened anybody who comes to Cuba's energy aid, that's particularly Mexico, with punitive sanctions if they do deliver fuel. Right now, as we're speaking, there is a Russian oil tanker on its way to Cuba, but there's no telling whether or not it's actually going to make it or not. One previously diverted at the last minute and ended up going to Trinidad, so they're not getting major oil shipments. Now. The private sector is being allowed, in theory, to bring in some supplies to cover its own needs, but those are minuscule and do not really address the issue at hand.

[Sarah Holder (Bloomberg News Host)]

And what half those three months effectively without oil at all, meant for conditions

[Jim Wiss (Bloomberg Reporter on Cuba)]

on the island, Conditions were hard to begin with, and now, you know, they're frankly quite terrible. There have been lots of reports, many of them unconfirmed, about people dying in hospitals as ventilators are getting cut off. That's part. And due to the power outages, which were endemic before the fuel crunch, but they've only gotten worse since then, Industry is grinding to a halt, and resorts, which are one of the big main money earners for Cuba, have had to shut down because there's not enough fuel. It's rippling all the way through society, and hunger is real. The United nations has basically said that the government can no longer deliver food and aid to kind of the most vulnerable parts of the population simply because they don't have enough gasoline to put in the cars. So it's dire.

[Sarah Holder (Bloomberg News Host)]

And what has that dire situation that's already been a struggle for many people in Cuba. How has that changed the political situation on the ground and people's attitudes towards their government?

[Jim Wiss (Bloomberg Reporter on Cuba)]

Well, you know, outright demonstrations, protests are essentially banned in Cuba. And yet there are more sounds, more rumblings of discontent over these last couple of weeks. There have been some very kind of high profile protests, including one in a little town called Moron where basically people got together and attacked the seat of the Communist Party in this town. So there's a lot of dissatisfaction on the street, some of it aimed at Washington, some of it aimed at the local authorities. I think there's a lot of blame to go around right now, but for the government itself, at least publicly, it's sticking to its ground.

[Sarah Holder (Bloomberg News Host)]

I asked Bloomberg's Eric Martin, who covers the State Department and foreign policy for Bloomberg, about why the US has been putting this pressure on Cuba and its economy, what its goals are.

[Eric Martin (Bloomberg State Department and Foreign Policy Reporter)]

Cuba has had patron states throughout the last 70 years. The US is really looking to follow in those footsteps in terms of a superpower that exerts great influence and control over the island. This is an administration that has articulated a national security strategy, an actual document released in December that is very focused on asserting US Preeminence and dominance in the Western Hemisphere. We've seen China in particular trying to establish a foothold and a presence in Cuba in recent years. We've seen this patron relationship that Venezuela had with Cuba for several decades, even going back to the relationship of the Soviet Union in Cuba in the 1960s. And so this has been a national security threat across different American presidencies. But it's also a priority for the Republican Party and for voters, particularly Cuban exiles in Florida. And this is administration that we see a lot of influence from Florida. And so there's a lot of constituents here that would like to see a change and an opening and a more democratic, more US Friendly Cuba.

[Sarah Holder (Bloomberg News Host)]

I am wondering, Jim, what role do Cuban Americans and Cuban expats play in all this? How are they reacting to the situation on the island?

[Jim Wiss (Bloomberg Reporter on Cuba)]

Well, that is really interesting. I think the diaspora has been waiting for this moment for 60 years. And they are interested in investing, they are interested in seeing changes in Cuba. The Cuban government kind of in theory, is trying to open the doors to that. Just in recent weeks, they have announced legislation that would allow Cuban exiles to invest in companies and own companies in Cuba and kind of participate in the economy. But there's still so many hurdles both on the US side and on the Cuban side. For that to actually happen, we shouldn't hold our breaths and wait for the wave of Cuban investors coming from Miami.

[Sarah Holder (Bloomberg News Host)]

You mentioned one of the ways that the Cuban government has been responding, but what steps have they taken? What signals have they sent over the last three months as the US has ratcheted up this pressure?

[Jim Wiss (Bloomberg Reporter on Cuba)]

It's interesting. I think one thing they've been doing is kind of acknowledging it. President Miguel d' Escanel has gone on national television a couple of times now and, you know, and basically said, yes, we're hurting. These U.S. measures are affecting us. And they keep describing as akin to collective punishment, everybody on the island's gonna suffer because of these U.S. policies. And so on one side, I think they are kind of acknowledging their vulnerabilities and their pain in a way that maybe they haven't in quite some time, acknowledging that the US is hurting them. And on the other side, again, for the lack of a better phrase, I think it's just defiance. They keep saying that, yes, we're willing to work around the margins, we're willing to let Cuban exiles invest, but we're not willing to discuss who leads our country.

[Sarah Holder (Bloomberg News Host)]

So without an obvious exit ramp, where could this all be heading? What paths is the Trump administration angling for? That's next.

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[Sarah Holder (Bloomberg News Host)]

I want to walk through some of the possible paths US Cuba relations could take from here, starting with diplomacy. Both the Trump administration and Cuban officials have confirmed they're in talks. So Eric, what do we know about who exactly is at the table and what each side is looking to achieve with these talks?

[Eric Martin (Bloomberg State Department and Foreign Policy Reporter)]

So we reported last month that the US Is looking to replace Cuban President Miguel Diaz Canel, that he is somebody who they see as having failed in terms of his economic management and his leadership in Cuba. We know that Raul Castro, the former president and the brother of Fidel Castro, his grandson, whose name is also Raul, he's called Raulito or sometimes his nickname is El Congrejo the Crab, has been having discussions with the Trump administration via Secretary of State Rubio. That's one name that we've seen out there as somebody who is more open, who is more of a global business minds, is more open to making a deal as less ideological. We saw an important signaling mechanism where in a recent speech by Miguel Diaz Canel, the President Raul Castro's grandson, he was in the room for that speech, which was very unusual. And so the Cuban authorities have acknowledged that these talks are going on. The US Is looking to use economic pressure, particularly by cutting off energy sales to the government, but permitting energy sales to the small but fast growing small and medium sized enterprise and businesses in Cuba to foster this private sector, which they then see as leading to a political opening in Cuba. So it's kind of the same in some ways similar to comparable to the process that we saw the attempts in Russia in the 1980s to have an economic and political opening.

[Sarah Holder (Bloomberg News Host)]

Yeah, well I want to talk about that potential opening because last week on March 16, the Cuban envoy to the US said the country is moving to allow more investment from Cubans Living abroad. How big of a change is that? And how did the Trump administration respond to that news? Is that the kind of deal that they're looking for here?

[Eric Martin (Bloomberg State Department and Foreign Policy Reporter)]

Well, Secretary Rubio has responded to that by saying it's not dramatic enough in terms of the kind of moves that the administration needs to see. And there's a lot of skepticism in the exile community about putting money into Cuba, investing money in Cuba with a government with a history of expropriation. Many of the people in the exile community in Florida are either from families that have themselves in living memory, had assets expropriated, or they can remember from their parents and grandparents what that experience was like. So there's a lot of skepticism to this offering by the Cuban government in terms of opening to outside investment. Just a feeling like this is not nearly enough for what people need to see in terms of. In terms of an opening and in terms of a democratization.

[Sarah Holder (Bloomberg News Host)]

And, Eric, in the lead up to these talks, and even as these talks are ongoing, members of the Trump administration have also implied that they could take a tougher approach in Cuba. Right after the US Captured President Maduro in Venezuela in January, Secretary of State Marco Rubio told reporters, quote, if I lived in Havana and I was in the government, I'd be concerned. And earlier this month, Senator Lindsey Graham told Fox News that, quote, iran is going down and Cuba is next. So, Eric, what do we know about whether the US Is considering a military option in Cuba?

[Eric Martin (Bloomberg State Department and Foreign Policy Reporter)]

Well, we haven't yet seen reporting of military preparations to invade Cuba or strike Cuba. But the rhetoric that we've seen from President Trump has been speaking about. Shortly after our story, he came out and talked about the idea of a potentially friendly takeover of Cuba. He's more recently entertained the idea that it could be a friendly takeover or not so friendly. And so he's teased this idea of using force in Cuba. Already, the threat of force and interdiction has stopped. For instance, Mexico, which was the main supplier of oil to Cuba after Venezuela, from sending oil to Cuba. And so we've already seen the threat of force at work here, Eric.

[Sarah Holder (Bloomberg News Host)]

We've talked about sort of three ways that the Trump administration is pursuing putting pressure on Cuba. The first is, you know, continued talks, diplomacy, deal making. The second would be military intervention. And the third would be using financial pressure to make Cuba dependent on the US do we know about which option the Trump administration prefers or which option would be most likely?

[Eric Martin (Bloomberg State Department and Foreign Policy Reporter)]

Well, one thing we've seen from President Trump's comments is that his expectation and his view is that Cuba wants to make a deal, but he's also talked about Cuba being dealt with. He's repeatedly said Cuba would be dealt with after Iran. So I think one important signal will be watching what happens with the current war in Iran if there is a de escalation or a negotiation to reopen the Strait of Hormuz to de escalate the conflict in Iran. And so attention, I think is likely to turn more to Cuba if there is a resolution or an easing of the conflict and the war in Iran.

[Sarah Holder (Bloomberg News Host)]

And Jim, I want to turn back to you here. The US has opposed the communist government in Cuba for decades, since the 1960s. How significant would any of these outcomes, a diplomatic resolution, a military intervention, an economic takeover, be in the sweep of Cuban history? And what message would they send to the rest of Latin America?

[Jim Wiss (Bloomberg Reporter on Cuba)]

I mean, this would be incredibly significant. I mean, as you've mentioned, ever since Kennedy, successive US Presidents have been trying to either force a change, negotiate a change, finesse a change in the island. And it's never happened. The government has always rallied. The government has always been able to protect itself. It's an incredible story of kind of political survival in Cuba. And so if they ended that 67 year run of single party rule, if Trump was the one to do it, that would be incredibly significant. There is this really romantic notion about Cuba in the Latin American left. I suspect that a Cuba that actually fell, that succumbed to Washington, would only increase kind of the nostalgia of what Cuba once was. I think we'll be dealing with the consequences of whatever happens in Cuba one way or another for decades to come in Latin America.

[Sarah Holder (Bloomberg News Host)]

This is the Big Take from Bloomberg News. I'm Sarah Holder. To get more from the Big Take and unlimited access to all of bloomberg.com, subscribe [e-mail] podcastoffer if you like this episode, make sure to subscribe and review. The Big Take. Wherever you listen to podcasts, it helps people find the show. Thanks for listening. We'll be back tomorrow.

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