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The Florida Keys War

Part 3


By Chris Oakley


Adapted from material originally posted at


Summary: In the first two instalments of this series we recalled the events leading up to the Florida Keys War, the early battles of the war itself, the impact of British and Mexican forces on the course of the fighting, and the political upheaval that shook the USSR after Khrushchev’s death. We open Part 3 with a look at the difficult choice facing President Kennedy as he debated with his aides over whether to authorize a nuclear attack against the Soviets after a U-2 was shot down…


Three Minutes to Midnight: June 15th-June 20th, 1961


It was just after 11:00 AM Eastern Daylight Time on the morning of June 15th when President Kennedy summoned JCS Chairman Taylor, General LeMay, Defense Secretary McNamara, and CIA director John McCone to his office for a meeting on the U-2 incident in Turkey. Kennedy and McNamara both felt that caution was warranted until more was known about the shoot-down; Taylor, while not as eager as LeMay was to start firing ICBMs, shared LeMay’s view that their alert status— which had been on DefCon 4 since the war started – should be raised at once, if only as a psychological ploy to make the Kremlin think twice about invading Turkey.

LeMay vehemently insisted that all U.S. nuclear forces should go to DefCon 1 immediately and told Kennedy point-blank that at the end of the meeting he would authorize Strategic Air Command chief of staff General Thomas Power to arm SAC’s ICBM silos in the continental United States and MRBM launchers in Europe whether the president agreed with it or not. This prompted a vehement protest from McNamara, who then got into a heated argument with LeMay and accused him of trying to circumvent SIOP; the argument ended with Taylor physically inserting himself between the two men to prevent them from coming to blows1. Moments later, Kennedy coolly told LeMay that if he went through with his plan, he would be summarily relieved of command.

As LeMay reluctantly conceded defeat, McCone showed the president a series of radio intercepts from the CIA’s listening posts in Istanbul and Tehran. They were messages between the SAM launcher that had shot down the U-2 and the headquarters of the Red Army regiment to which the launcher was attached; although they were incomplete and there was still more investigation to be done, the CIA director said that these transcripts indicated the shoot-down was accidental, the result of an apparent electrical short in the SAM’s arming mechanism.

At about five minutes past noon, Kennedy made his decision: the ICBMs’ alert status could be raised to DefCon 3, but neither they nor the MRBMs in Europe were to be armed until the Soviets’ intentions became clearer. With that, LeMay made a hasty exit back to his office while McNamara accompanied Taylor back to the Pentagon for a debriefing on Operation Marti2, the projected US & allied offensive to take Havana.




Back on Cuban soil, the battle for San Cristobal had begun in earnest. For the first time anti-Castro Cuban insurgents, who up to that time had been operating largely in small groups, took on their Communist enemies en masse, destroying two Cuban regular army outposts and capturing a third for advancing US and Mexican troops. The last remnants of the Cuban air force were eliminated during this engagement as US Air Force F-4 Phantom IIs shot down nearly two dozen Hawker Sea Furies3 while American armor and infantry occupied key military and industrial bases inside the city.


It was during this engagement that US Army Special Forces officer Roger Donlon earned the first Congressional Medal of Honor to be awarded in the Florida Keys War. Despite shrapnel wounds to his right arm as the result of a Cuban Communist mortar barrage, he led his 12-man A-Team on a successful hit-and-run raid to knock out an enemy artillery position that had been shelling US ground troops non-stop since the battle began; he then covered his team’s escape and helped a squad of local anti-Castro insurgents safely evacuate the city before finally allowing a Medevac chopper to fly him to a field hospital in Cabo san Antonio for treatment and recuperation.

For three days both sides anxiously awaited the outcome of the San Cristobal engagement; not only was it a critical waypoint on the road to Havana, but it also housed at least two airfields. If the city were to fall into U.S. & allied hands, it would be the most devastating blow yet to a regime which had already sustained a number of painful setbacks…




While Kennedy and LeMay were arguing about whether to arm the United States’ ICBMs, Castro had made his biggest — and as it turned out, last —mistake of the war. Considering it urgent that he return to Cuba immediately so he could rally his people to victory, he persuaded CPSU First Secretary Brezhnev and Defense Minister Malinovsky to lend him the K-3, a November-class nuclear Submarine, for a secret run to Havana Harbor4. Although Raul Castro considered such a trip risky, Fidel insisted it could be done without a significant risk of the Americans detecting them.

On June 17th, as U.S. infantry and tanks advanced on the heart of San Cristobal, K-3 put to sea at full speed with orders to get Castro back to Havana at all costs. His brother Raul and Raul’s wife Vilma Espin were nervous about making the trip in such tight quarters, so Castro did his best to keep up their spirits with songs and stories of their days fighting the Batista government. 

Luck seemed to be on the Castro brothers’ side as K-3 slipped past NATO patrols undetected on its journey to Havana Harbor. Once they got ashore, however, their luck would desert them in swift and spectacular fashion; CIA and MI5 had already launched a manhunt for them and were offering a $1,000,000 reward for their arrest…




Back in Moscow, Leonid Brezhnev had convened an emergency meeting of his cabinet to get their assessment on the situation in Turkey and Germany as well as the latest news on the battle for San Cristobal. What he heard wasn’t encouraging: the Americans, his advisors told him, were refusing to back down in Europe, and barring a miraculous reversal of fortune San Cristobal was all but lost.

Right then and there Brezhnev made two of the hardest decisions of his political career. First he ordered the cancellation of Operation Anatolia— by now he had concluded that an invasion of Turkey would do more harm than good as far as Soviet national security was concerned. He then told Andrei Gromyko to order all remaining Soviet diplomatic and advisory personnel to begin immediate preparations for possible evacuation from Cuba; though he said he still thought Castro might yet recover from the blows the Americans had dealt him, the Soviet government had to brace itself for the possibility that he wouldn’t.

Defense Minister Malinovsky was shocked at Brezhnev’s decision and urged him in the strongest possible terms to reconsider it. But the CPSU first secretary saw no alternative: an invasion of Turkey at this juncture was sure to trigger a stiff response from NATO — one that might very well include full-scale nuclear attacks against the Soviet Union5.




Once Kennedy was satisfied that Operation Anatolia had in fact been cancelled and the invasion force disbanded, he ordered NATO forces in Europe to stand down from DefCon 3. He then retired to Camp David for a much-needed three-day vacation before returning to the White House to meet with Defense Secretary McNamara and the Joint Chiefs of Staff on the final draft of the battle plans for Operation Marti.

In his absence, Britain’s famed SAS commando service would pull off its most spectacular triumph since World War II. On June 20th, just before 8:00 PM Havana time, the SAS parachuted a six-man demolitions squad into Santa Clara, where the Cuban Communists were known to be stockpiling weapons and ammunition as part of preparations for their last-ditch attempt to invade the Caymans. Though there was little chance by now that the battered remains of the Cuban navy could break the U.S. & allied blockade of their homeland, Macmillan’s government wasn’t taking any chances; those munitions, he rightly pointed out, could still be used by Cuban Communist troops to oppose the coming American drive on Havana.

Using explosive charges planted inside the main munitions storage facility, the SAS men succeeded in triggering a chain reaction that in less than ten minutes obliterated the Cuban Communists’ entire stockpile in Santa Clara. The demolitions team then fought its way to a pre-arranged pickup site near the town of Ranchuelo, reaching their destination with the loss of only one team member, a sapper fatally wounded by machine gun fire.

Che Guevara, already in a fragile mental state, went berserk when he learned about the British commando raid and had to be taken to a Havana hospital to undergo treatment for a nervous breakdown. Juan Almeido Bosque, who next to Che was Castro’s most loyal follower, took over as acting head of the Cuban government and armed forces and ordered security at all remaining munitions facilities in the country heightened.


Operation Marti: June 21st- July 7th, 1961


On June 21st, Fidel and Raul Castro along with Vilma Espin returned to a Cuba even more firmly under the control of the United States and its allies than it had been when he left for Moscow 18 days earlier. Prime Minister Macmillan had finally released the Royal Army’s troops in the Caribbean from garrison duty to assist American and Mexican ground forces in eliminating what was left of the Cuban Communist army; even as Castro’s party was stepping ashore from K-3 at Havana Harbor, the Queen’s Own Parachute Regiment had seized Sagua la Grande and Royal Army mechanized infantry were driving for Santa Clara to complete the job their SAS comrades had started 24 hours earlier.

Returning to the presidential palace, he was greeted with the news of Che Guevara’s hospitalization and the loss of the munitions supplies at Santa Clara. Devastated by these twin blows to his regime, Castro ordered that the naval vessels which were to have been used for the now-thwarted invasion of the Caymans be re-assigned to a last-ditch strike aimed at retaking Cabo san Antonio from U.S. and allied forces. This operation, dubbed Choque y Temor6, has been compared by some military historians to the Germans’ Wacht am Rhein offensive in the final months of World War II; a more appropriate metaphor, however, might be the Japanese kamikaze attacks suffered by Allied forces in the days and weeks up to Hiroshima. For the remnants of the Cuban navy were, in effect, being sent on a suicide mission.

On June 22nd, as the world marked the 20th anniversary of the Nazi invasion of Russia, these remnants, along with a motley assortment of civilian craft carrying hastily assembled volunteer squads, departed Guanabo — by then one of only three ports in Cuba still under Communist control – with orders to attack U.S. and allied forces at Cabo san Antonio and retake that vital seaport in the name of Castro’s revolution.

However, shortly after putting to sea the flotilla found a nasty surprise waiting for it… or more accurately, eighteen nasty surprises. A joint US-British task force of hunter-killer submarines was lying in wait to ambush the naval ships in the convoy, and as soon as they got the Cuban Communist vessels in their sights they let loose with the most ferocious volley of torpedoes seen in Caribbean waters since the Battle of the Florida Straits. All but one Cuban warship was sunk in the attack, and most of the civilian craft perished as well; the remaining civilian ships either fled back to Guanabo or were scuttled by their crews.

News of the failure of Castro’s 11th-hour effort to retake Cabo san Antonio from the Americans shattered what was left of Che Guevara’s spirit. Three days after Choque y Temor was defeated, the Argentine-born Marxist icon took a borrowed World War II-era Soviet pistol and blew his brains out; in official Cuban government accounts of his death, however, he was portrayed as having given his life heroically while manning an anti-aircraft gun during the latest round of American bombing raids on Havana. It would be up to the Voice of America’s Spanish-language broadcast service to bring the Cuban people the truth about Guevara’s fate.




On June 26th, British forces mopped up the last pockets of Cuban Communist resistance in Santa Clara and Sagua la Grande and began moving on Cienfuegos to link up with anti-Castro Cuban insurgent units. The question was no longer if or even when Fidel’s regime would collapse, but whether he would live to see the aftermath. Between daily U.S. and allied air strikes, the growing civil unrest in Havana, and a somewhat justified fear of assassination, the surviving members of his inner circle suspected he might not be long for this world.

And it wasn’t just the war itself that had them worrying for their leader’s future— war-related stress had taken a serious toll on Castro’s health. Since the Las Tunas mutiny he’d been having persistent stomach troubles, and he’d also been diagnosed as having a heart condition that would eventually require him to undergo surgery. At least a third of his journey back to Cuba on board K-3 had been spent being treated by the ship’s surgeon for high blood pressure.

Those concerns would only deepen after the Cuban dictator was admitted to Havana’s Hospital Clínico Quirúrgico on June 27th with an ulcer that had started right after Che Guevara’s death and grown steadily worse until it could no longer be ignored. Raul Castro, in addition to his regular duties as Cuba’s defense minister, was now also called on to take the helm as its acting head of state.

He ordered security around Hospital Clínico Quirúrgico tightened to frustrate those who might seek to collect on the $1,000,000 reward for Castro’s arrest. He also withdrew two full battalions of tanks from Guines — where they had been guarding the southern roads to Havana against possible US assault – to defend Mariel, whose only value by now was as a jumping-off point for those wanting to get out of Cuba before the Communist regime’s final downfall.

By June 28th, the number of foreign embassies still operating in Havana had dwindled to a handful— and that number would drop even further as the North Korean legation closed its doors for good and evacuated its last remaining personnel by freighter to China. China’s own embassy would be shut down within 36 hours, leaving just the Soviet, Swedish, Finnish, Swiss, and East German embassies still in business by the time US and allied forces were ready to begin Operation Marti. 




On July 2nd, Guines fell to American troops while British forces linked up with anti-Castro Cuban insurgents at Cienfuegos, which effectively gave the U.S. coalition control of more than 85% of the country’s overall land area. Before the day was out, Kennedy had given General Harkins the go-ahead to start Operation Marti as soon as his offensive spearhead was in position.

Operation Marti’s objectives were threefold: (1)Isolate Mariel and Havana from the rest of the remaining Communist-controlled territory in Cuba; (2)eliminate what was left of the Castro regime’s ability to wage war on the ground; and (3)secure Havana so order could be restored in that city. In JFK’s eyes, the third goal was by far the most important; the latest CIA reports had told him that the Cuban capital was teetering on the verge of an anarchy almost as dangerous as anything it had seen during the final days before the Batista regime collapsed. 

On July 5th, backed by massive air strikes and guerrilla assaults from the anti-Castro Cuban forces, U.S. and allied troops began Operation Marti. Within just 12 hours after the assault started, Bahia Honda and Guanajay were in American hands while British forces succeeded in crushing a Communist attempt to recapture  Cienfuegos; by dawn on July 6th, U.S. army tanks were slugging it out with Cuban Communist armored battalions on the outskirts of Mariel.

Soviet ambassador Alexander Alekseyev decided that he couldn’t afford to wait any longer to get his people out. He requested and got Moscow’s authorization to evacuate his remaining staff from Havana, then contacted the East German embassy — then in the midst of its own hasty evacuation – to say a last farewell to the East German ambassador.

At noon on July 6th, U.S. Air Force B-52s and RAF Vulcans raided Havana for the last time. As part of a tacit agreement between Washington and Moscow, the city’s harbor was spared to avoid killing anyone among the Soviet or East German embassy staffs during their evacuation from the Cuban capital. The rest of Havana, however, was hit so relentlessly some of its citizens thought there might be nothing but dust left of it by the time the Americans arrived.

Back at Cabo san Antonio, a mixed group of local anti-Castro Cubans and Cuban-American exiles who’d been living in Florida since Castro took power met to begin hammering out the rough outlines for a post-Communist government in Havana. These men and women, though they might not have agreed with everything Kennedy did, all shared his concern about the disorder which was sweeping Havana’s streets as the Castro dictatorship choked out its last breath.

Time was running out not only for Fidel’s government, but for Fidel himself; while he was trying to recover from his ulcer operation, the Cuban Communist tyrant had suffered a massive stroke, rendering him helpless against those who wished to arrest or kill him. Sensing this, an orderly at Hospital Clínico Quirúgico surreptitiously sent a message to the advancing U.S. and Allied forces telling them where they could locate Castro. The CIA was quick to capitalize on this lead…


To Be Continued



1 Relations between LeMay and McNamara, which had never been all that cordial in the first place, became downright frosty after this confrontation; it’s believed that the fallout from his argument with McNamara may have influenced LeMay’s decision to retire from the US Air Force barely a year after the Florida Keys War ended.

2 Named in honor of Jose Marti, the Cuban revolutionary who led the rebellion that ultimately gained his country’s independence from Spain.

3 A piston-engined fighter plane originally created for service with Britain’s Royal Navy during the Second World War; several of this type had been sold to Cuba in the waning days of the Batista regime and were still in service to the Cuban Communist forces when the Florida Keys War started.

4 Castro had originally hoped to make the journey in the experimental Hotel-class sub K-19, but Malinovsky advised him against it. The defense minister was probably right to do so; on July 4th, during its maiden voyage in the Atlantic, K-19 suffered a catastrophic reactor accident and was lost with all hands. The nuclear submarine’s grim last hours were fictionalized in the 2002 Kathryn Bigelow movie K-19:The Widowmaker.

5 Though Malinovsky himself never commented about it publicly, many of his associates believed— and still believe –that his distress over Operation Anatolia’s cancellation may have been a major contributing factor in his physical decline and eventual death from heart failure in 1965. For a glimpse of how the rest of his life, and the war, might have played out had the invasion gone forward as planned, read Wade G. Dudley’s essay "Morning In Byzantium: The Soviet Invasion Of Turkey, 1961" in Peter G. Tsouras’ book Cold War Hot.

6 Literally, "shock and awe"; Castro hoped the element of surprise would work in his favor and offset the U.S.-led coalition’s airpower advantage.


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