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The Florida Keys War

Part 1


By Chris Oakley


Adapted from material originally posted at


The Two Toughest Kids On The Block: April 30th-May 16th, 1961


On the surface it looked like Cuban Communist overlord Fidel Castro had achieved his greatest political triumph since his overthrow of the Batista regime two years earlier. He’d faced down and defeated an attempt by CIA-backed counterrevolutionary troops to land an invasion force at the Bay of Pigs and given President John F. Kennedy a black eye in the process. Now, it seemed, his grip on power was secure and the Americans would think twice before challenging him in his own backyard again.

In reality, though, the Bay of Pigs incident had sparked a chain reaction that would ultimately spell the doom of the Castro regime and deal a sharp blow to the global prestige of his chief foreign ally, the Soviet Union. For the Cuban ruler, convinced the United States was a pushover, made an ill- advised decision to retaliate for the invasion by mounting an attack of his own against the islands of the Florida Keys.

On April 30th, 1961, two weeks after the Bay of Pigs assault, Castro ordered his top generals to draft plans for a combined air and sea attack on the western tip of the Keys; his intent was to occupy them as part of a bold gambit in which he would use the Keys as a bargaining chip to force JFK’s administration to close the US naval base at Guantanamo Bay.

The proposed assault, code-named Operation July 26th1, was set for late May and involve 13 warships and 160 aircraft. Besides the Florida Keys operation, there were provisions for diversionary attacks against the Guantanamo Bay installation to keep American forces off-balance.

Convinced that his patrons in Moscow would share his desire to capitalize on his victory at the Bay of Pigs, Castro phoned the Soviet embassy in Havana in early May and invited the embassy’s military attaché to accompany him on an inspection tour of the Cuban bases from which Operation July 26th would be launched. The attaché’s reaction was not what Castro had expected, however: he told the Cuban leader in no uncertain terms that the invasion should be postponed until the Soviets could muster a sufficiently large military force in the area to back the landings up.

But Castro wouldn’t hear of it; the Yanquis were ‘paper tigers’2, he asserted, and would quickly grow tired of the fight. Operation July 26th would go forward, and it would be a smashing success. 


As distressed as the Soviet military attaché in Havana was about Castro’s stubbornness, he would have been truly alarmed had he known that word of the planned attack was already starting to get back to the White House through the CIA. Even as Castro and his generals were laying the foundations for Operation July 26th, a mole at the Cuban embassy in Mexico City had cabled Washington that Havana was in the first stages of preparing an assault on the Florida coast.

About the same time as Castro and the Soviet attaché were on their inspection tour, President Kennedy began holding a series of late-night conferences with his top military and diplomatic advisors to discuss what measures could be taken to stop the looming invasion in its tracks. Though there were some disputes as to what specific steps to take, Kennedy’s aides were united on three crucial points: (1)the United States could not afford to show even the slightest sign of hesitation or weakness in the face of the invasion threat; (2)whatever action was going to be taken to stop Operation July 26th had to be taken quickly; and (3) further evidence of Cuba’s aggressive intentions would have to be obtained and presented to the UN if Washington hoped to gain any foreign support for its response to Castro’s actions.

Fortunately for the White House, such evidence wasn’t long in coming. On May 8th, a U-2 dispatched from Homestead Air Force Base in Florida brought back photos clearly showing a massive build-up of ground and air forces along Cuba’s eastern tip; two days later CIA sigint3 personnel intercepted a cablegram from Castro to the Cuban embassy in Moscow instructing his ambassador there to meet with Soviet leader Nikita Khrushchev and work to change the CPSU general secretary’s attitude regarding Operation July 26th.

On May 11th, American ambassador to the UN Adlai Stevenson showed both the photos and the cablegram to the General Assembly. The Soviet delegates, understandably chagrined to realize that Moscow and Havana had been metaphorically caught with their hands in the cookie jar, made no comment throughout the entire session; the Cuban delegation, on the other hand, vehemently denounced the US ambassador as "a verminous little liar"4 and gave further vent to their displeasure by walking out of the session in protest. At 7:30 PM US Eastern time that evening, President Kennedy delivered a televised speech in which he announced the establishment of a ‘tripwire’ air and naval defense line along the Florida coast; if any Cuban ships or aircraft crossed that line, he said, it would be regarded as an act of war against the United States to which his administration would respond by authorizing air strikes on every major military and industrial facility in Cuba. A similar ‘tripwire’, involving Marine air and ground personnel, would be set up at Guantanamo Bay.

Kennedy’s proclamation was greeted with apprehension in Moscow; for all his bluster about burying the West, Soviet premier Nikita Khrushchev understood that the slightest miscalculation by the Cuban government— or his own —could have fatal consequences for the socialist bloc. In addition to having what was widely seen as the world’s best conventional military, the United States also held a considerable edge over the Soviet Union in nuclear arms, particularly when it came to ICBMs.

On May 13th, at Khrushchev’s request, the Soviet embassy in Havana again urged Castro to postpone Operation July 26th; he dismissed their worries with an overconfident smile and told the embassy’s third secretary that ‘my troops will march all the way to Miami if they have the chance!’5.

Kennedy, and his Joint Chiefs of Staff chairman General Maxwell D. Taylor, were determined to make sure Castro’s army never got that chance. Not only were all Air Force bases in Florida, Alabama, and Louisiana on full alert, but every Navy submarine which could be spared from patrol in the Atlantic was included in the Florida ‘tripwire’ line; furthermore, the Army’s famed 101st Airborne Division had been activated and the 82nd Airborne was being held on standby reserve pending further orders.

The day after Castro’s meeting with the Soviet embassy staff in Havana, Kennedy approved Operational Plan 307, a strategy for a combined land, air, and sea campaign against Cuba. This plan, of which the projected Air Force raids on major Cuban military and industrial targets was to be a major component, would be activated at the first sign of a Cuban move against the Florida Keys or Guantanamo.

At 11:56 PM on May 16th, the main assault force for Operation July 26th departed from Cabo san Antonio; it consisted of six destroyers, eight corvettes, twenty patrol boats, nine diesel submarines, and an indeterminate number of landing craft. Most of the ships in the landing force were of Cuban or Soviet manufacture, but many were, ironically, US-built vessels that had been sold to Cuba back when Batista was still in power.

While this armada was travelling the 90 nautical miles which which separated Cuba from Florida, 3 squadrons of Cuban MiG-17 fighters were escorting an equal number of Il-28 bombers towards the edge of U.S. airspace; to confuse American radar personnel, the Cuban planes flew in an irregular pattern over as wide an area as possible, and when they reached U.S. soil they would drop to treetop level to deny anti-aircraft defenses any chance to hit them before they struck their designated targets.

Everything seemed to be going according to plan...


The Tripwire Crossed: May 17th-May 21st, 1961


...but as the old saying goes, sometimes the best-laid plans of mice and men go astray. At 12:42 AM on the morning of May 17th, the Skipjack-class nuclear submarine USS Scorpion detected the Cuban Communists’ Florida Keys invasion force on their sonar screens 40 nautical miles south of Key West. They immediately reported the sighting to the aircraft carrier USS Ranger, the designated flagship for the naval task force assigned to monitor the Florida ‘tripwire’ perimeter. Ranger, in turn, contacted the US Atlantic Fleet headquarters in Norfolk, Virginia; within less than fifteen minutes word of the sighting had reached the White House.

At 1:00 AM US Eastern time, President Kennedy phoned Defense Secretary Robert S. McNamara with a single terse directive: "Activate Op Plan 307." No sooner had he hung up than both the naval and air components of the Florida ‘tripwire’ sprang into action. The Ranger and her sister ship Independence, along with the Midway-class carrier USS Coral Sea, scrambled planes to stop the invasion force while land-based F-102s moved to intercept the Il-28s and their MiG escorts.

What followed was the biggest air and sea battle fought by American forces since Midway. The Cuban surface ships and their American foes traded salvo for salvo while the waters beneath them churned as both sides’ respective submarines unleashed furious torpedo volleys; one of the Il-28 squadrons was diverted from its original targets on land in a desperate attempt by the Cubans to neutralize the American carriers. At 1:10 AM the Ranger’s captain ordered all his ship’s available strike aircraft launched against the Cuban task force.

By this time, US Air Force chief of staff General Curtis LeMay had authorized his SAC squadrons in Florida, Georgia, and Alabama to begin hitting Cuban military and industrial targets as outlined in the air component of Op Plan 307. "Bomb the SOBs back into the Stone Age" was his succinct directive to the bomber units, and they were more than happy to oblige— for the B-52 and B-58 crews, already hopping mad at the Communists to begin with, Castro’s attempt to invade the Florida Keys was the last straw.

At 2:17 AM, air raid sirens abruptly broke the night time silence in Havana as the first wave of B-52s came in at treetop level and began bombing the Cuban capital’s factories, naval outposts, and anti-aircraft batteries into rubble. The second wave came in just fifteen minutes later and took out of most of Havana’s airfields and utility plants6. Though the Cubans managed to shoot down five aircraft and capture their crews, for the most part they’d been caught napping.

Shortly after the second wave of B-52s made its run on Havana, US Chief of Naval Operations Admiral George W. Anderson visited the White House to debrief Kennedy and McNamara on what was already being called the Battle of the Florida Straits. While it would be some time before the full results of the engagement were known, he had received confirmation that five of the six destroyers in the Cuban landing force, including its flagship the Project 7-class destroyer Bayamo7, had been sunk along with seven patrol boats and all but one of the submarines. The total number of Cuban landing craft sunk, he admitted, could not yet be reliably calculated, but he was confident that his task force had made it very difficult if not impossible for the invasion force to mount even a token assault on the Florida Keys.

US air defenses, meanwhile, had shot down 80% of the Il-28s and 55% of the MiGs committed to the Florida Keys assault, and of the planes that weren’t shot down at least a third returned to Cuba so badly damaged they would require days if not weeks of repair work before they could be put back into operation. "Now we’re eyeball to eyeball with Castro." Kennedy told White House assistant counsel Kenny O’Donnell when the debriefing was over. "It’s just a question of who blinks first."


It was 10:30 AM Moscow time when Nikita Khrushchev first learned of the battle raging in the Florida Straits and the American air strikes on Havana. An aide to the Soviet military attaché had phoned the CPSU general secretary with a rough précis of Castro’s invasion attempt and Kennedy’s response; just as Khrushchev had feared would happen, his Cuban allies had taken a severe beating in their attempt to invade the Florida Keys. Of the 100,000 Cuban troops assigned to the first wave of the planned Keys assault, at least 80,000 were known to have been killed in the Battle of the Florida Straits and another 1500 had been reported missing.

To make matters worse, the losses which the Cuban air force had sustained in the Florida Straits clash and the B-52 raids on Havana were being compounded by tactical strikes on other Cuban air bases. A-6 Intruders out of Pensacola Naval Air Station and F-100 Super Sabres from Homestead had started bombing fighter airfields all over western Cuba, and Soviet intelligence reports indicated that there was a possibility of additional strikes out of MacDill and Patrick within the hour.

In a blind fury, the CPSU general secretary phoned the Cuban ambassador in Moscow and assailed him with a torrent of epithets more befitting a Minsk factory worker than the leader of the world’s most powerful socialist state. In less-than- polite terms, Khrushchev made it clear that he considered the Florida Keys invasion a catastrophic mistake for which the entire socialist bloc would inevitably pay; he also made at least one unflattering remark about Castro’s family background8.

When Khrushchev’s two-hour harangue was finally over, the Cuban ambassador said to an aide in a dry understatement: "The General Secretary seems less than pleased with the way the fighting down in Key West is going9."


General LeMay’s decision to eschew his B-52 squadrons’ normal high altitude tactics in favor of treetop-level attacks during the first American raids on Havana has long been a subject of heated debate among Cold War scholars. LeMay’s critics argue that by ordering them to fly in at low altitude for those first raids on Cuba, he exposed his flight crews to unnecessary risk while at the same time increasing the likelihood of civilian casualties.

But his defenders assert that the change in tactics actually worked to the bombers’ advantage; they argue that the switch disoriented the Cuban air defense forces and denied them any opportunity to mount a coherent opposition to the B-52 and B-58 raids. Furthermore, they suggest that a lower altitude meant the bombs would reach the ground faster, which according to their viewpoint would decrease the risk of civilian losses.

In any event, General LeMay felt that he had little choice in the matter— two weeks prior to the Battle of the Florida Straits his own staff had warned him that if the Cubans went ahead with their invasion plans most of the Air Force’s tactical assets would initially be needed to suppress the landing force. The bombers, they suggested, would have to wait until at least the third day of the war before they could resume their customary high-altitude attacks.

At 3:00 AM US Eastern time President Kennedy gave the go-ahead for the 101st Airborne to begin making airdrops on Cabo san Antonio and Isla de la Juventud. Simultaneously the 82nd Airborne was activated and given orders to secure a beachhead at the port of Cárdenas. While this was going on, elements of the 3rd Marine Expeditionary Force were en route to Guantanamo Bay to strengthen its defenses against a possible Cuban ground attack.

The remnants of the Florida Keys invasion force staggered back to Cabo san Antonio just in time to see the main advance units of the 101st Airborne descending on the very harbor from which they’d set out on their assault attempt less than five hours earlier. A brief but ferocious firefight ensued which ended with most of the Cuban sailors being taken prisoner.

With many of Havana’s phone lines knocked out by the B-52 and B-58 raids, Castro’s generals found it difficult to co-ordinate any sort of effective counteroffensive against the US paratroopers entrenched at Cabo san Antonio or Isla de la Juventud. More to the point, their enforced delay in responding to the initial US air and ground assaults gave the 3rd MEF critical extra time to strengthen the ‘tripwire’ line at Guantanamo Bay. When the attack on Guantanamo finally came, it would meet such bitter opposition from the Americans that one full division of the Cuban army would literally be wiped out to the last man10.

Vice-President Lyndon Johnson was at his ranch in Texas when he first learned the United States was at war with Cuba. Just after 5:00 AM Eastern time, he flew back to Washington on Air Force Two and drove to the Pentagon for a full debriefing on the initial clash between US and Cuban forces at the Florida Straits; shortly after the debriefing he met with President Kennedy at the Oval Office and strongly recommended that the chief executive and his entire family and staff be prepared to evacuate the White House if the Soviets showed any intention of using nuclear weapons to respond to the American ground and air offensive. Kennedy felt a full evacuation was premature but did accede to Johnson’s advice to have First Lady Jacqueline Kennedy and her children Caroline and John Jr. flown by helicopter to the Kennedy family estate at Hyannisport. He also authorized the relocation of part of his cabinet to the Mount Weather underground bunker in West Virginia.

At 6:05 AM Eastern time, as his family was boarding Marine One, Kennedy made a televised speech from the Oval Office formally declaring that as of 1:00 AM a state of war now existed between the United States and the Republic of Cuba11.


Next to General Taylor— and President Kennedy himself —no man in JFK’s administration had a tougher task than Secretary of State Dean Rusk, who had the twin daunting assignments of (1) delivering the message to Castro’s Soviet patrons that America would not back down from defending its interests and its honor and (2)lining up foreign support for the US military campaign in Cuba. Ironically, America’s longtime ally Great Britain was the toughest nut to crack when Rusk sought international backing for military action against Cuba— then-prime minister Harold MacMillan was still somewhat bitter about the part that Kennedy’s predecessor, Dwight Eisenhower, had played in stopping Britain’s intervention in the Suez crisis five years earlier, and some of the more left-leaning members of Parliament felt that what was happening in the Florida Straits was nothing more than Washington getting its just deserts for its actions during the Bay of Pigs.

Even setting those factors aside, there was the stark truth that Britain had already made extensive commitments to NATO and was just beginning to rebuild Malaya after that country’s vicious 12-year-long guerrilla war. Thus, MacMillan was understandably less than enthusiastic about committing British ground troops to yet another regional conflict in a tropical country.

Rusk, however, succeeded in persuading MacMillan to send air and naval forces to the Bahamas and Jamaica to assist US personnel in Cuba; in return, MacMillan obtained from Rusk a guarantee of US financial aid to Britain’s reconstruction efforts in Malaya.

Mexico’s co-operation was the easiest to obtain; the government of Adolfo López Mateos12 was tired of the Castro regime’s constant attempts to foment insurrection among the Mexican working class, and they also feared that if Castro succeeded in his Florida Keys venture he might go after Mexico’s oil fields next. A force of 5,000 troops and 150 combat aircraft was assembled and sent to Cabo san Antonio to support the US landings in that region.


By noon on the first day of the Florida Keys War, American troops at the western tip of Cuba had advanced as far as Mantua; in the east, the 3rd MEF had not only repulsed Cuban attempts to capture Guantanamo Bay but were cutting off Cabo Maisi and the town of Baracoa from the rest of the country. Meanwhile, at Cárdenas, the 82nd Airborne was steadily expanding its beachhead and tanks were being offloaded there in anticipation of a possible armored push against Matanzas.

That push came at 7:30 AM on the morning of May 18th as three Army and two Marine tank battalions initiated a four-column thrust on the Cuban seaport. The Cubans struck back with a fierce armored assault of their own; the boldness of their attack briefly forced the Americans into retreat.

However, Kennedy had learned many critical lessons from the Bay of Pigs disaster, the most important of those being not to give in to the temptation to quit at the first sign of Cuban resistance. The American tank forces soon dug in their heels, and by 10:30 AM they were on the outskirts of Matanzas chasing their Cuban counterparts towards Santa Cruz del Norte.

Castro and his brother, then-Cuban defense minister Raul Castro Ruz, were alarmed at the way the situation was developing-- this was most certainly not how they’d expected things to turn out when they first thought of Operation July 26th. Less than 36 hours after their invasion fleet had departed Cabo san Antonio, Cuba’s armed forces had lost 47,836 men, 320 combat aircraft, and 67 warships; American losses by contrast totaled just 1841 men, 51 aircraft, and 6 warships13.

And the Castro regime’s troubles weren’t over yet; even as the first American tank shells were exploding in front of the Cuban defensive lines at Matanzas, Mexico’s expeditionary force to Cuba had already established its headquarters in Cabo san Antonio and a British task force of 23 ships and 145 aircraft was preparing to depart from the Royal Navy base at Scapa Flow. Headed up by the Audacious-class aircraft carrier HMS Ark Royal, this group, designated "Special Operations Unit Caribbean" by the Ministry of Defence, would have the responsibility of not only supporting the US-Mexican coalition’s operations in Cuba but also guarding the Cayman Islands against possible Cuban attack.

Though certain cynics on both sides of the Atlantic questioned the legitimacy of MacMillan’s (admittedly reluctant) support for Kennedy’s actions vis-à-vis Cuba, Britain did have real interests to protect in the Caribbean. Many of the islands adjacent to Cuba were or had been members of the Commonwealth of Nations, and just about all of them still had close ties with London; furthermore, these islands were home to tens of thousands of British nationals who had to be protected. Finally, MacMillan and his Secretary of State for War, John Profumo, shared the uneasy feeling that if Castro were to succeed in his Florida Keys venture, his Soviet benefactors would feel encouraged to expand their then-token military presence in Cuba— which might trigger a chain of events pushing the world into full-scale nuclear war. Castro, MacMillan and Profumo decided, had to be nipped in the bud.


American forces reached San Juan y Martines early on the morning of May 20th. Matanzas had already surrendered by then, and the 3rd MEF was taking up positions on the outskirts of Baracoa. Despite the Castro regime’s iron-fisted control over Cuba’s broadcast and print media, hints of the military catastrophe being inflicted on its armed forces were trickling back to the Cuban public with a small bit of help from Voice of America’s Spanish-language radio service.

Around 7:00 AM Eastern time air elements of the 3rd MEF, working with US Air Force fighter jets out of southern Florida, started bombing Cuban defensive positions on the outer edge of Baracoa. Half an hour later, the 3rd MEF’s ground contingent made contact with the Cuban regular army and a firefight ensued the likes of which American soldiers hadn’t experienced since the first wave hit Omaha Beach on D-Day. The Cuban ground forces, motivated both by Communist zeal and national pride, opposed the 3rd with everything they had. A Soviet journalist attached to the Cuban garrison at Baracoa commented in his account of the engagement to the official government newspaper Pravda: "After a certain point, I found myself wondering whether this battle was being fought by men or demons14."

In the end, however, the American advantage in numbers and equipment would tip the scales in the 3rd’s favor, and around 2:27 PM that afternoon Baracoa was secured. For the next 24 hours after that, there was little if any ground fighting in Cuba as both sides paused to consolidate their supply lines and regroup their forces. The air war was a different story; it continued without letup, particular the B-52 raids on Havana and the F-100 strikes on Cuban bases near San Cristobal.

Indeed, even as the last pockets of Cuban resistance in Baracoa were being mopped up, the Joint Chiefs of Staff had given their consent for tactical strikes against industrial and military targets in the vicinity of Cuba’s second largest city, Santiago de Cuba. The raid was scheduled for 8:30 AM on the morning of May 21st


At 8:00 AM Moscow time on the morning of May 21st, 1961, KGB Chairman Alexander Shelepin received an urgent phone call from his station chief in London. He had a feeling it would be bad news, and sure enough the station chief’s first words confirmed his fears: "The British task force to Cuba15 put to sea two hours ago…"


On to Part 2



1 A reference to the 1953 army barracks attack that launched Castro’s career as a revolutionary.

2 An expression coined by his closest friend and top political advisor Che Guevara.

3 Signal intelligence.

4 And that was the mildest thing they said about him; many of the comments they made in response to Stevenson’s statement were so obscene that the entire Cuban delegation was publicly reprimanded by UN Secretary General Dag Hammarskjöld for foul language.

5 Off-the-cuff remark believed to have been made during a telephone conference between Castro and the Soviet embassy staff.

6 One unintended but welcome result of the B-52 strikes was that the panic and confusion—not to mention direct hits from two stray bombs—enabled hundreds of political prisoners to escape from the maximum security wing of the infamous La Cabana prison.

7 Originally launched as the Revostny and sold to Cuba by the Soviets in late 1960.

8 A detailed though somewhat bowdlerized transcript of Khrushchev’s conversation with the ambassador is still on file today at the historical archives of Moscow State University.

9 The ambassador didn’t know, of course, that the landing force had never gotten anywhere near Key West.

10 According to the front page story "Gitmo GIs Throw Back Castro’s Men", from the May 18th, 1961 edition of the New York Post.

11 The president’s official helicopter.

12 Mexico’s president from 1958 to 1964.

13 According to official Defense Department records.

14 The journalist was later chided by his editors for what they called "excessive emotionalism".

15 The station chief’s shorthand way of referring to the Royal Navy’s Special Action Group Caribbean.




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