Fumbling Into Havana

Before resolving the crises already consuming American power, Washington appears poised to open a new confrontation ninety miles from Florida.

We’re fumbling into a new conflict, even as we’ve failed to finish the one we’re already in.

This time, the administration is picking a fight closer to home. We’re talking about Cuba.

President Trump has long had a tense relationship with Cuba. In the first six months of his first term as President, he reversed the short-lived Cuban Thaw, set in motion by his predecessor President Obama. In June 2017, Trump issued a prohibition on travel to Cuba, reimposed sanctions, and characterized the thaw as ‘terrible and misguided.’

This week, it looks more likely than any time in the past 60 years that the United States is poised to intervene in Cuba in a significant manner. So, let’s go back and explore what’s going on and what’s the background.

The United States and Cuba have long had a strained dynamic.

Cuba was a Spanish colony for four hundred years beginning when Christopher Columbus claimed the island in 1492 as Isla Juana, until the Cuban War for Independence in the last decade of the nineteenth century.

The Cuban War of Independence was the final of three liberation wars and was fought 1895-1898. In the final year of the war, the United States sent the ship the U.S.S. Maine to Havana, ostensibly to protect American interests there. The Maine carried more than 5 tons of explosive charges for its guns, and about two weeks after its arrival, the charges detonated killing 261 service members.

The remains of the U.S.S. Maine after salvage

‘Yellow journalism’—the intellectual predecessor of clickbait—from the New York Journal and New York World blamed Spain, triggering the Spanish-American War. It must be noted that there is no certainty as to the trigger of the explosion. It could have been a small Spanish mine, as suggested by the initial investigation (the Sampson Board) and supported by the Vreeland Board of Inquiry. It could have been a false-flag operation, as suggested by several Spanish speaking media services and proposed in Operation Northwoods. Most likely, it could have been a near-spontaneous combustion as proposed by Admiral Rickover in his investigation in the 1970s.

Regardless of the cause, the result remained the entry of the United States into the war against Spain, with Congress passing a declaration of war on April 25, 1898.

Following the war, the United States enacted the Platt Amendment which outlined the conditions for withdrawing U.S. forces from the island, and requiring a treaty between Cuba and the United States. This became the Cuban-American Treaty of Relations of 1903, which ensured long-term U.S. leasing of Guantanamo Bay (for $2,000 / year, later adjusted to $4,085) and authority for the United States to unilaterally intervene in Cuban affairs. This second provision was later abrogated in a 1934 revision of the treaty, but only after the United States occupied Cuba and established a provisional government for three years, 1906-1909.

For the next half century, the relationship between the United States and Cuba was relatively close—akin to a big brother-little brother relationship. For example, during the First World War, Cuba abandoned its policy of neutrality a day after the United States entered the war, following its big brother’s lead.

Similarly, after Japan attacked the United States at Pearl Harbor, Cuba—a lend-lease beneficiary—entered the Second World War on the side of the Allies.

Throughout most of the war, Fulgencio Batista served as Cuba’s president. Following his term, he retired to Florida until deciding that he wasn’t actually done ruling the island. He returned to Cuba to run for president in 1952, but facing near-certain defeat, decided that the safer route to power lay through a coup d’etat (it should be noted that Batista originally came to influence through a coup d’etat in 1933 called the Revolt of the Sergeants). The United States quickly recognized Batista’s government, legitimating it.

Batista’s golden telephone served as a symbol of excess, indulgence, and corruption. Golden telephone? Maybe that’s what this is all about after all…

However, neither Batista nor his policies were popular in the 1950s. Socialist revolutionary currents ran deep, upset about Batista’s theft of office—particularly given that their preferred candidate Roberto Agramonte was the clear frontrunner for election.

Just a year after Batista’s coup, Fidel Castro’s M-26-7 revolutionary movement initiated the Cuban Revolution with attacks on the Moncada Barracks in Santiago de Cuba and Carlos M. de Cespedes Barracks in Bayamo. While the attacks failed (Castro was jailed), they set in motion the revolution that would overthrow Batista’s government, see Castro rise to power, and set Cuba on a path as disparate from America’s as imaginable.

For much of the revolution, the United States actively supported Batista. Not only was the United States concerned about the rise of Marxist ideologues in its backyard, but—more importantly—U.S. economic interests were heavily invested in Cuba. According to then Senator John F. Kennedy:

At the beginning of 1959 U.S. companies owned about 40 percent of the Cuban sugar lands - almost all the cattle ranches - 90 percent of the mines and mineral concessions - 80 percent of the utilities - and practically all the oil industry - and supplied two-thirds of Cuba's imports.

Eventually, however, the United States realized it was supporting a loser in Batista, and so we ended our support in 1958. First we suspended arms sales, later we imposed an embargo. But it was too late, the perception of the United States as supporting a corrupt, kleptocratic despot was cemented in the minds of the Cuban peasants. So, when Castro’s revolution succeeded and Batista resigned and fled the country, the relationship was severely damaged.

That damage was cemented in 1961 during the Bay of Pigs incident, when CIA-trained militants attempted a disastrous invasion of Cuba. The militants, known as Brigade 2506, consisted of around 1,500 men. Of those, 114 died in the attempted invasion and another 1,183 were captured, tried, and imprisoned. It took a private effort to coordinate a ransom payment for these prisoners.

Revolutionary Cuba turned towards its ideological brethren in the Soviet Union. The Soviets saw an opportunity to neutralize the perceived American advantages in nuclear power, and so they began positioning their own nuclear weapons in Cuba. The Cuban Missile Crisis eventually resolved through backchannel diplomatic masterwork, narrowly avoiding nuclear catastrophe.

Cuba then embarked on a campaign of exporting its socialist revolutionary ideology and supporting other Marxist and Marxist-aligned movements around the world and particularly in the Southern Hemisphere. For example, Cuba backed:

• The People’s Movement for the Liberation of Angola (MPLA) through arms, training, and direct action fighting against the Portuguese, the Portuguese-backed Angola government, and against the South African military.

• The Sandinistas (FSLN) in Nicaragua, securing the release of Sandinista leaders, providing sanctuary and training for them.

• The People’s Liberation Army of Namibia (PLAN) in Namibia, with arms, training, intelligence, and direction action fighting against the South African military and South West Africa Territorial Force.

• The African Party for the Independence of Guinea and Cape Verde (PAIGC) in Guinea-Bissau with artillery expertise and weapons.

• The National Liberation Front (FLN) in Algeria as the first government to recognize Algerian independence from France and supporting the nascent Algerian government in its war against Morocco with arms and troops.

• The Conseil National de Liberation (CNL) also known as the Simba rebellion in Congo.

This is not an exhaustive list of Cuban support for revolutions and Marxist movements.

It’s also important to note that many (if not all) of these organizations engaged in what could be considered terrorist tactics at some points in their existence.

Therefore, when the Secretary of State Marco Rubio categorized Cuba as a ‘state sponsor of terrorism’, there is truth to that categorization. In fact, the U.S. government designated Cuba in 1982. That designation was lifted by President Obama in 2015, but President Trump reinstated it in 2021 at the end of his first term.

Yes, this is a year old…

This however is a day old.

So, there is truth to Cuba being a state sponsor of terror.

Categorizing them as a ‘leading’ state sponsor of terror might be overstating the case, however.

Most of those organizations that received Cuban support did so in the 1960s and 1970s. Some (Sandinistas and PLAN) received it in the 1980s. What’s more, Cuba supported Hugo Chavez in his takeover and destruction of Venezuela and propped up Nicolas Maduro, after Chavez’ death.

At the heart of the U.S. Department of Justice indictment against Fidel Castro’s brother and former Cuban president Raul Castro, is the downing of flights over Cuba run by an organization called Brothers to the Rescue, in 1996. Now, the Federal Aviation Administration raised internal concerns about Brothers to the Rescue flying over or near Havana in attempts to provoke the Cuban government and military.

You know what they say: FAFO.

Cuba filed multiple complaints about the flights. The U.S. government warned Brothers to the Rescue to stop their provocation. But the organization persisted. As such, it’s hard to feel overly sorry. Like we said, FAFO. Brothers to the Rescue did, in fact, FAFO. It’s also important to remember Max Weber’s political philosophy and definition of a state which includes ‘the monopoly on the legitimate use of physical force in the enforcement of its order.’

In other words, we may not like Cuba’s action, but it was largely legitimate and it’s a hard sell to suggest that this was a terrorist act. Citing Raul Castro’s role as DefMin at the time is also a stretch.

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But the real question is whether, and to what extent, Cuba represents a national security threat to the United States.

Rubio is correct that Russia and China have presences in Cuba. That includes SIGINT posts capable of capturing signals from parts of the United States. Is that an existential threat to the United States or its interests? No. No, it’s not.

It’s also true that Cuba is acquiring modern military technology like one way attack drones. The claim about their discussions on using those drones to attack Guantanamo Bay is much harder to verify. The reality is that every military prepares various plans for operations and contingencies. Just as U.S. combatant commands maintain plans for nearly every conceivable scenarios (admittedly in varying levels of preparation based on risk), it’s probable that any Cuban conversation about using attack drones against Guantanamo was as part of contingency planning. Nevertheless, we cannot rule out the possibility that the conversations were part of an opportunistic planning effort for random cost imposition.

Regardless, the risk to U.S. interests—including at Guantanamo—from Cuba remains relatively low and certainly doesn’t cross the threshold for direct military intervention.

To be clear, Cuba is not an existential military threat, but it is part of a larger geopolitical contest in the Western Hemisphere. Its geostrategic location near America’s southern coast, its relationships with Russia and China, its growing telecommunications infrastructure, and its willingness to engage in mutual antagonism with the United States all mean that despite relatively limited capabilities, the risks it poses cannot be summarily dismissed.

So, here we are fumbling into another potential conflict that shouldn’t be a conflict at all, before we’ve cleaned up our most recent mess.

We had the chance to open relations and pull Cuba back into the orbit of the United States. But we squandered that opportunity in 2017, preferring to hold grudges in perpetuity.

Now, we have the opportunity to resolve our differences without resorting to the military. This is the perfect sort of scenario where other elements of national power can prove far more efficacious. But, we’ve squandered and defunded and folded our smart power, preferring to invest only in coercive power.

Should it come to military action, it will most likely look far more like Operation Absolute Resolve than Operation Epic Fury. But that doesn’t mean it’s the correct or most effective way of helping bring Cuba forward towards a legitimate, rules-based, and (classically) liberal democracy.

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Operation Epic Fury (Iran)

• Trump says Iran talks are in the final stages (CNBC)

• Marines board Iranian-flagged tanker amid blockade (AP)

• Iran, Oman hold talks over Hormuz Strait ship payment system (NYT)

• U.S. intel finds Iran is reconstituting its military industrial base faster than faster than original estimates (CNN)

• Iran’s Ayatollah issues directive that enriched uranium must stay in Iran (RT)

• Trump vows US will retrieve uranium from Iran in any deal (RT)

• U.S. clears scrap dealer to buy ships sanctioned for Iran activity (WSJ)

Operation Zapata II (Cuba)

• Justice Department charges former Cuban President Raul Castro with murder, conspiracy as U.S. seeks to pressure the island (AP)

• U.S. military jets and drones tracked near Cuba as tensions rise (BBC)

• U.S.S. Nimitz aircraft carrier in Caribbean as U.S.-Cuba tension mounts (MT)

• SecState Rubio says likelihood of diplomatic solution with Cuba ‘is not high’ (PBS

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News Headlines

• Capitol police sue to block payouts to Jan 6 rioters (NPR)

• Senate GOP, frustrated with Trump’s $1.8B payout fund, delays vote on ICE money (WP)

• House Republicans pledge ‘we’re going to kill’ Trump’s $1.8B ‘anti-weaponization’ fund (TH)

• SpaceX predicts TAM at $28.5T in IPO filing to justify inflated valuation (BI)

• SecState Rubio, SecArmy Driscoll contradict Trump on Ukrainian strengths (DN)

• Lithuanian lawmakers shelter, Vilnius air traffic suspended due to drone incursion (DN)

• Pentagon Inspector General to review boat strikes (NYT)

• Trump announces 5,000 troops to deploy to Poland a week after deployment cancelled by Pentagon (AP)

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Defense & Dual-Use Technologies 

• Chief of Staff of the Air Force thinks F-35s, F-15s can fulfill combat search-and-rescue role of A-10 Warthogs (DO)

• Air Force dubs MQ-9 the ‘MVP’ of Epic Fury, despite significant losses (MT)

• CENTCOM chief wants money to attack hardened, deep-buried targets (DO)

• Foolhardy Trump-class battleship will strain already-limited shipyard capacity (DIE)

Threat Tech

• Services rebuff SecDef Hegseth’s lax flu policy, seeing health threat to forces (MT)

• Thieves are cloning trucks and blowing up Texas oil pipelines (MW)

• Leaked papers reveal Russian-Chinese military tech transfers and partnerships, including Ka-52M attack helicopter, airborne-capabilities, more (DSA)

• Chinese defense companies suggest new long-range military sniper milestone set (IE)

• Taiwan: China deploying over 500 converted J-6 fighter-jet drones (TN)

• Russia launches unannounced nuclear exercise, including Belarussian launch sites (DN)

• Russia develops new version of its Su-57 Felon fighter (DB)

Foreign Defense Tech

• NATO ACT commander: Europe has no alternative to Palantir‘s tech (POL)

• NATO eastern deterrence strategy takes shape around ‘autonomous zone’ (DN)

• Germans lose faith in the U.S. and turn to defense (EN)

• Italian leaders see energy costs as bigger threat than defense challenges, reconsider spending priorities (DN)

• Italy settles on Airbus tanker purchase in swing toward European equipment (DN)

• Poland joins Pentagon’s counter-drone marketplace amid unexpected U.S. deployment drama (MT)

• Sweden picks France’s FDI frigates in potential $4.2B deal (DN)

• Turkey to buy 100 one-way explosive naval drones for swarm attacks (DN)

• Ukrainian ground bot fights off Russian advances for six weeks (DO)

Defense Industry

• Defense groups clamor to delay U.S. ban on Chinese rare earth magnets (FT)

• Perennial Autonomy wins $500M deal for counter-drone tech (DN)

• Klein Marine Systems unveils UUV that can detect mines, conduct surveys (IE)

• Lockheed ramps up missile production in Camden, Arkansas (WSJ)

• Northrop wins $325M to develop drone that monitors hypersonic tests (DB)

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Autonomous Systems 

• Senators express concern about slow Pentagon policy updates on autonomous weapons (MT)

• Navy SEALs in mini-subs teamed with underwater drones in the works (TWZ)

• Carrier-based MQ-25A Stingray approved for low-rate production (DN)

• Drones are forcing consideration of distributed operations (TP)

• U.S., Korea agreement creates ‘drone alliance’ for shared systems, logistic (SS)

• Shahed-136 clone LUCAS to get hivemind swarming capability from Shield AI (TWZ)

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Finance & Deal Flow

Funds

• Michal Strnad, the Czech billionaire founder of defense giant CSG, is launching an investment firm with potentially $12B to target acquisitions in Europe and U.S. (BBG)

VC

• Bootstrapped custom manufacturing startup SendCutSend raised a $110M debut round at a $1B valuation co-led by Sequoia, Paradigm and Stripe co-founders Patrick and John Collison (WSJ)

• Quartermaster, a maritime sensing startup, raised a $43M Series A co-led by First Round Capital and Quiet Capital (TC)

• Arkeus, a defense technology company building AI-powered sensing systems, raised an $18M Series A led by QIC Ventures (PU)

PE / M&A / Exits / Other

• Germany will seek to acquire a 40% stake from German investors in Franco-German tank maker KNDS to match France’s ownership ahead of its IPO which could fetch a $25B valuation (RT)

• KNDS plans to sell 2% of its 16% stake in German engineering firm RENK Group for $312M at a 3% discount ahead of its IPO (BBG)

• Dutch weapons maker Destinus is in talks to raise $235M in a pre-IPO round (TFN)

• Nuclear startup Deep Fission is seeking to raise $156M at a $1.7B valuation in an IPO (BBG)

Debt

• German defense giant Rheinmetall plans to raise $580M in its first public bond sale in 16 years (BBG

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Exciting Opportunities

• The Office of Naval Research is looking for enabling technologies to support hypersonic boost-glide vehicles (SAM)

• The Army Corps of Engineers has issued a CSO looking for a broad range of capabilities to support its information technology lab; tech areas range from cyber resilience to digital engineering to advanced computing to autonomy (ERDC)

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Editor’s Picks

• Bob Savic at Geopolitical Intelligence Services outlines how China is testing its military tech through exports to Russia and now Iran.

• Our friends at Fox and Lion suggest the announced drawdown of U.S. troops from Europe isn’t concerning and just continues a years-long trend.

• BoF Founding Member David Lewis shares insights around digital engineering in the maritime industry.

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Lighter Side

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Keep Building,

BOF

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