The Jewish Revolutionaries of Key West

Martí visited Key West twice more in 1892. During one of these visits, he met with leaders of the Jewish community, at Steinberg’s invitation. For Martí, this was a strategic necessity—among these men were the leaders of Key West’s growing Jewish merchant class, from whom he hoped to raise funds for his revolution. But Martí also genuinely seemed to find resonance in their life stories: In his appeal, he touched on the historic struggle of the Jews and the recent persecutions that had forced these men to flee to a speck of an island across the globe from their homes in Romania and imperial Russia, where many still had relatives, including wives and children, for whom antisemitic terror remained a fact of daily life. Martí connected these trials to the struggles of his own people, and the despotism and cruelty they suffered at the hands of their Spanish oppressors. “With all, and for the good of all” had been Martí’s rallying cry, and he now pleaded with the Jews of Key West to support the cause of liberty, not simply for Cubans, but for all people.

Florida politics has long been shaped by the nationalist passions of Cuban exiles and diaspora Jews, which have evolved in close proximity. Today, Florida is home to the third-largest Jewish population in the United States, and nearly two-thirds of all Cubans living in the US live in Florida (including approximately 10,000 Cuban Jews). These communities skew considerably more right wing than Jewish and Latin American communities elsewhere in the United States; both communities’ support for President Donald Trump outperformed their national counterparts. The state has long been a bastion of hardline foreign policy regarding Israel and Cuba, with elected officials from both parties offering the former an open palm and the latter a closed fist. At times, the two communities have drawn political inspiration and fortitude from one another: In the early 1980s, Jorge Mas Canosa, a prominent businessman and political operator in the Miami Cuban exile community, founded the Cuban American National Foundation to ad­vance the community’s policy aims in Washington—an effort explicitly modeled after the pro-Israel lobbying group AIPAC. A February 1988 Miami Herald article from a series on “Miami’s Power Elite” features a story about how trips to Israel organized for local leaders by the Jewish Federation forged friendships and “cooperative fund raising” between the Jewish community and Canosa’s foundation; one Cuban American participant talked about how “the story of the Jewish diaspora reawakened her own feelings of loss for her homeland, Cuba.” (This sentiment was echoed after the Hamas attack on southern Israel on October 7th, with Cuban-born US Congressman Carlos A. Giménez, who represents Florida’s 28th District including Key West, explaining on X: “Everyone knows that I am Pro-Israel . . . I lost my native homeland of Cuba to a murderous gang of terrorists who continue to oppress my people—I don’t wish that upon anyone.”) The close relationship between the Cuban American Senator from Florida, Marco Rubio, and Jewish American billionaire Norman Braman, who was a major financer of Rubio’s 2016 presidential run, was apparently kindled over their shared immigrant backgrounds. “Unlike the people in politics who were born on third base and think that they hit a triple, Senator Rubio comes from a background similar to mine,” Braman once said, referencing his parents’ humble beginnings in Eastern Europe.

Few are aware that these political affinities go back more than 130 years, to the Jews of Key West and their support for Martí’s revolutionary nationalism—a nationalism that would pave the way for early expressions of Zionism in the region. Despite the current alignment of the Cuban and Jewish diaspora in Florida with American empire, initially such solidarities were rooted primarily in an anti-colonial ideal, strengthened by a shared experience of oppression. These solidarities were made manifest over the late 1880s and early 1890s in the founding of a Jewish cell of the Cuban Revolutionary Party by a number of Jewish merchants and community leaders who found common cause with Cuban exiles seeking independence—going so far as to run weapons to their comrades on the other side of the Florida Straits.

By 1888, Jewish firms controlled almost three-fourths of the US market for raw tobacco and were even better represented as manufacturers of finished cigars. Of the 65 members composing the National Cigar Manufacturers’ Association that year, 45 were Jewish. For their part, it appears that Jewish factory owners were not active in insurrectionary efforts against the Spanish colonists: Their success depended upon relationships with Spanish tobacco growers in occupied Cuba, as well as a multiracial workforce of Cuban-born Spanish subjects who labored in their Key West factories. Indeed, at least one Jewish manufacturer, Samuel Seidenberg, earned the bitter enmity of the insurrectionists of the 1890s when he sought to replace striking workers at his factory with Spaniards.

But, following a devastating fire on the island in 1886, a new generation of Jewish immigrants began arriving in Key West—a generation that had fled the pogroms and persecutions of Europe and had little in common with the Jewish cigar manufacturers who preceded them. The manufacturers were older, more secular, and far wealthier than the new peddlers and shopkeepers, who were younger and hungrier, with less to lose and more to gain, and with the bitter taste of their most recent exile still fresh. Many of Key West’s Jews frequented the neighborhood called El Barrio Gato, where Cuban cigar rollers, Eastern European Jewish merchants, and freed slaves lived alongside rich and powerful Cubans like military general Serafín Sánchez and the neighborhood’s namesake, cigar manufacturer Eduardo Gato himself. José Martí would lodge in this neighborhood during his visits to Key West.

The sympathies that developed between the Jewish and Cuban communities in Key West were rooted in similar political plights. The island 94 miles south of Key West was still a colony of the Spanish Empire. Native-born Cubans were denied fundamental rights readily afforded to Spanish citizens. White Cubans were not allowed to own property, nor have any say in government; Black and mixed-race Cubans were regarded as property themselves, confined to the tobacco plantations where they were enslaved by the Spanish ruling class. Jews from the likes of Russia or Romania during the same period had not been allowed to own land or work in professions of their own choosing. Many Jews also saw Spain as an enemy of the Jewish people, since its persecution of the Jews under the Inquisition had continued until 1834, an era within living memory for the elders of the community, which contributed to a shared hatred for the Spanish Empire among the Cubans and the Jews of Key West.

This affinity was reflected in the writing of Martí, who helped reenergize the on-again, off-again movement for Cuban independence in the 1890s. A poet and journalist by trade, Martí was an acute observer of the human migrations of the late 19th century, and his reportage displays a particular sensitivity to the Jewish plight: “These are grave times for the Jews,” he wrote in early 1882, as the “May Laws” of Tsar Alexander III, which curtailed the freedoms of Jews and encouraged mob violence from ethnic Russians, began to be enforced. “They have been expelled from Russia, and they are chased through the countryside like wild animals.” He reported approvingly on a protest gathering in New York, where Americans had assembled to denounce the Russian actions as “a crime against humanity that should appall all peoples and grieve the heavens.” In his internationally syndicated Spanish-language column, he pleaded with his readers to hear “the anguished cries of the followers of Moses.”

Martí’s political genius lay in his ability to capitalize on the sense of exile as a unifying force, and to propose a transformative vision of salvation through battle. In this regard, his eloquent expression of the exile experienced by many Cubans was often framed in explicitly Jewish terms. “We are Jews in point of fortune,” Martí wrote, “and we hope always for a Messiah who never comes.” He was a student of Jewish history during his university studies in Spain, where he became proficient in basic Hebrew. In the story of the Maccabees, who successfully fought under Mattathias for Judean independence from the Seleucids, Martí saw a model for the successful insurrection he hoped to lead: a rebel army that overcame powerful rulers through a successful guerrilla campaign. And in contemporary Jews, he found examples of the fortitude and commitment that such a revolution would require: “From their religion, the Jews make their homeland . . . They still feel that ardor which led their ancestors to take shelter under the banner of Mattathias . . . [and] to spread out like the angry sea over plains and mountains.” Even as he portrays the never-ending disappointment of exile, and the fruitless wandering in search of an absent Messiah, Martí is never far from posing a solution: “There is only one way to see the Messiah come, and that is to sculpt him with your own hands.”

This rhetoric was echoed by Martí’s general Carlos Roloff Mialofsky, a distinguished Polish Jewish veteran of the Cuban revolutionary forces, who rallied the neighborhood Jews to support the revolution. Born in Warsaw in 1842, Mialofsky had learned the art of war as a Union soldier during the American Civil War, before taking up the cause of Cuban independence. In Key West, Mialofsky met frequently with members of the Jewish community in the home of General Sánchez, a distinguished veteran of two prior Cuban revolutionary attempts. The multilingual Mialofsky likely provided a crucial link between the Cuban leadership of the revolution and the Yiddish-, Russian-, Lithuanian-, and Polish-speaking members of Key West’s Jewish community. In an important 1892 address, Mialofsky, speaking in Polish-accented Spanish, presented his own life history as an example to a mixed-race and multinational crowd: “Compatriots,” he began:

I am the son of unfortunate Poland, I am Polish and my country is a prisoner of three terrible tyrannies: the Russian tyranny, the Austrian tyranny, and the Prussian tyranny. I long for its liberty, as well as cry for its misfortunes. Destiny has been adverse to us Poles, but because I cannot offer my life for the country of my birth, I put all of my efforts for the freedom of that other land where I have lived among heroic men, that land for which I have spilled my blood defending the rights of its sons.

The Spanish word “polaco” is generally translated as “Polish,” or “Polack.” But among the Spanish-speaking Cuban exile community of Key West, “polaco” was often used as a shorthand for “Jewish,” whether the Jew in question was actually Polish or not, since many Cubans at the time knew few Poles who were not Jewish. So when Mialofsky identified himself to his audience—“soy polaco”—many listeners would have heard “I am Jewish.” And when he argued for a Cuban rebellion as a solution to the sort of tyranny “los polacos” had suffered in Russia, many in his audience would have understood that defeating the Spanish would be a victory for Jews and Cubans alike.


The leaders of Key West’s Jewish community were moved by the eloquent appeals from Mialofsky and Martí, and they offered their support to the revolution. They soon agreed to pool their resources and donate to the Cuban Revolutionary Party, the Martí-led body that coordinated rebel efforts during Spanish rule. Inspired by their generosity, and eager for their continued support, Cuban leaders invited members of the Jewish Alliance—a group founded by Key West Jews in 1891 for the purposes of “mutual aid and political action”—to formally establish a cell of the Cuban Revolutionary Party, and in December 1892, Patria announced the establishment of Club Abrabanel, composed of 50 Key West Jews. The club was named for the great Jewish statesman, philosopher, and financier of 15th-century Portugal, Don Isaac Abrabanel, who was a legend for his defiance of Spain during the Inquisition. Now the Jews of Key West would carry on Abrabanel’s struggle, chasing Spain out of the new world and taking revenge for the diaspora it had initiated. For Louis Fine—a Vilnius-born grocer and El Barrio Gato resident who acted as the local leader of Jewish religious life—the connection was clear. The short biography he later approved to appear in the 1918 volume Prominent Jews of America explained “he played a prominent part in the Committee which sought to create the independence of Cuba, sending men and ammunition out of the United States. He saw in this a part of Jewish vengeance against Spain, the old persecutor of the race.”

Club Abrabanel was initially dedicated to raising funds for the Cuban Revolutionary Party. Fine’s family remembered him riding through town on a horse, whose saddlebags he filled with the money he collected for the party as he visited friends, neighbors, and fellow sympathizers. After relocating to Tampa, Joseph Steinberg—brother of Edward, who had first invited Martí to speak to the Jewish community—assumed the official role of tax collector for the party. “All the Cubans dealt with them,” wrote General Fernando Figueredo, describing the crucial role the Steinberg brothers played within the Cuban exile community in Key West and Tampa. “When it came time to serve Cuba, they were themselves Cubans. They placed Cuba before their own colony, and therefore they did so much more than Cubans.”

By January 1895, the armed phase of the Cuban struggle had begun, and Jewish partisans in Key West evolved from a fundraising role to one of direct involvement in the acquisition, storage, and distribution of weapons to the warring rebels on the front lines. The United States technically remained at peace with Spain, and so it was imperative that the guerrilla operations in which Key West’s Jews participated were conducted in secret. Although the precise details of successful smuggling missions remain obscure, family anecdotes and personal recollections of those who were involved, together with official law enforcement and diplomatic accounts of failed operations, provide a general outline of the sort of missions Key West’s Jewish rebels were involved in.

In the spring of 1896, roughly one year after Martí had been killed in battle, a powerful steam-powered tugboat known as the Three Friends completed at least three successful deliveries of weapons to the rebels still fighting in Cuba. Its principal owner was the future Florida governor Napoleon Bonaparte Broward, but some archival materials implicate the close involvement of members of Key West’s Jewish community, including Louis Wolfson, a Russian dry goods merchant. Ships like the Three Friends depended upon an elaborate network of secret storerooms and warehouses near the coast, where caches of guns, ammunition, dynamite, machetes, and cannons could be held without arousing suspicion. Fine’s family told stories indicating that his Duval Street grocery store, downstairs from the room where the community met for religious services, was in fact used by Fine to store weapons for the rebel army, and that his efforts had attracted the curiosity of federal investigators. On one occasion, according to a descendant named Lois Cowan, police showed up at the store hoping to conduct a search and were chased away by Louis’s wife, Cadie, wielding a butcher knife. Just two days after the completion of a May 19th mission that delivered a large cargo of ammunition to Santa Clara, Fine personally met with Marcos E. Rodriguez, a known arms trader who had recently been released from El Morro, the Spanish dungeon near Havana Harbor, for similar activities to those conducted by the Three Friends. A few weeks after their meeting, Rodriguez set out on another mission aboard the Three Friends, though this one was foiled, as authorities discovered the crew attempting to transfer an enormous cargo of weaponry—including machetes, rifles, revolvers, dynamite, six Hotchkiss guns, and a powerful, lightweight revolving cannon—from another ship to the Three Friends.

Another of Fine’s plots on behalf of the Cuban rebels involved the 72-foot, shallow-draft schooner Competitor. On April 20th, 1896, the Competitor left Key West under cover of darkness, carrying 48 men, many cases of rifles, dynamite, and some 38,000 cartridges of ammunition. When a Spanish gunboat overtook the Competitor near the Cuban coast, three men were killed and several more were captured, including an American citizen named Alfredo Laborde, who served as the ship’s captain. Laborde was quickly tried in a Spanish military court and sentenced to death. He was eventually freed, thanks to the vociferous intervention of President William McKinley’s administration, but only after he spent 17 months in El Morro prison. Throughout his ordeal, Captain Laborde stuck to his unlikely story: that he had left Key West peacefully for Lemon City (a farming community that is now Miami’s Little Haiti), that he had been hijacked by Cuban revolutionaries, and that he had been forced by the hijackers to take on the load of arms and sail with it to Cuba. Whenever he was asked, Laborde gave the name of the ship’s owner as Joseph Wells, a Key West sponge fisherman. However, many years later, Joseph Fine, Louis’s son, would attest that the Competitor had in fact been owned by his father, and that Captain Laborde had been working for Fine. Furthermore, the younger Fine stated that his father purchased a second ship, also named the Competitor, and that this ship successfully—and apparently without detection—inflicted significant damage upon Spanish forces over a series of military excursions.