A ca. 1943 photo of Dominican dictator Rafael Trujillo (1891-1945).
The Dominican Republic's position in Caribbean politics had always been interesting since the Confederate purchase of Cuba in the 1870s. Nestled between Confederate, British, and French possessions, the country naturally inclined towards allying with the Entente, however this relationship would be increasingly challenged as the US and Germany poured investments into such countries as Venezuela, Honduras, and, most importantly, Haiti. As the world's first black republic founded as a result of a slave rebellion, Haiti became seen as an important thorn in the South's side to vengeful Northern politicians, and supporting the country in the midst of continued Entente strangling of the Caribbean market was deemed as a top concern to many as early as the 1890s after the humiliating defeat in the Second Mexican War. This US support for Haiti would be enough to see the country form a mutual defense pact with America just prior to the outbreak of the First Great War, a pact that would continue to blossom as the 1920s wore on.
By the mid 1930s, however, the situation had taken a radical change for the worse. By then Jake Featherston had assumed power in the Confederacy, and revanchist governments had also taken hold over Britain and France. In Mexico a more hardline right wing government under Francisco Jose II was propped up by the Confederates, a government which increasingly threatened the tentative peace that had so temporarily settled over Latin America. To make matters worse the global depression would see the US' Socialist administration retreat into a bout of isolationism, drastically reducing aid for Haiti and the overall US presence in this long troubled region just when it was needed the most. In it's vacuum stepped such strongmen as Rafael Trujillo.
Trujillo was far from a Freedomite or Actionist, but he saw many opportunities that aligning with the Confederacy could provide. By 1941 he had developed a reputation as a harsh dictator, brutally cracking down against any internal threats that popped up. In 1938, with help from members of the Confederate Sestapo, he purged his country's military and police ranks of any perceived enemies, effectively ending any possible internal threat to his rule. While this was ongoing Trujillo would develop a cult of personality around himself that, as one Northern newspaper put it, rivaled even Featherston's in pervasiveness and totality. All Dominican families were required, starting in 1936, to have a portrait of Trujillo in their homes, and starting not long after that decree the Dominican ruler would mandate that the country refer to him as "El Jefe" and not president, mirroring Featherston's informal nicknames "Sarge" and "Leader." All children were required to participate in various pro-Trujillo youth programs that indoctrinated youngsters into "proper" lines of thinking and even encouraged such behavior as turning family members in for "politically incorrect behavior." A special gang of secret police called "El 42" was created with assistance and training provided by Confederate and Mexican officials, who likewise planted seeds of Freedomite racial policy in the country's mindset.
Although brutal against his people, Trujillo was an ardent admirer of some of the Confederate conservationist efforts, and quickly attempted to pattern his country's environmental and social policies along those of Featherston's. Parkland was expanded, and the slash and burn technique of agriculture was likewise banned in an oddly controversial decree in 1939. Attempts at establishing better public hospitals and other works were also undertaken, often with considerable investment from various Entente members, and even some non-Entente members. The Dutch were quite active in terms of investments into the Dominican economy as late as May 1941, and generally pro-US Brazil also invested a considerable sum of cash into the country's burgeoning light industrial sector (mostly focused around textiles and cigar making).
It wouldn't be until 1941, however, that Trujillo would officially align the Dominican Republic with the CSA and make the fateful decision to enter the Second Great War on the side of the Entente in September of 1941 after the stunning success out of Ohio. Despite being a small and relatively backwater nation, the Dominican Republican had a decently sized and equipped army as a result of Confederate and Mexican investment, and this was a fact that the Confederates would take full advantage of come their November 1941 invasion of Haiti. Although a promoter of so-called "open doors immigration" (famously allowing Jews escaping from the Russian pogroms to seek asylum in Dominica against protests from France and Britain), Trujillo was an ardent proponent of the so-called "Antihaitionismo" - Anti-Haitianism. Really Featherston had no need to hold "discussions" concerning the "race question" with the Dominican leader for both he and his Dominican Party (the sole legal party in the country) were quick to blame Dominica's economic woes on the black Haitian refugees and immigrants that poured across the border in the wake of the economic depression. Initially the government policy towards them was rather light, being simple deportation of blacks caught illegally crossing the border, however this radicalized in the wake of the Freedomite takeover of the South. Soon a policy of outright segregation and extreme discrimination was implemented, and by 1941 many Haitians had found themselves locked in Dominican concentration camps.
The Dominican Republic would play a crucial role in the invasion of Haiti in late 1941, intervening after Trujillo had chalked up a series of recent border incidents as a casus belli to invade. As a result of their participation the Dominican Republic was allowed control over parts of the borderland, annexing much of it into the country by 1944. Afterwards things remained quiet as the Central Powers remained occupied fighting around Pittsburgh and the Rhineland, but that was soon to change. In early 1943 the US would destroy the Confederate pocket around Pittsburgh, and in return the South was in desperate need for more men. In March of 1943 a desperate Featherston turned to Trujillo to supply the South with two "volunteer" brigades promising to use them solely against black guerrillas in Mississippi and Alabama. Threatened with possible invasion from Haiti and moribund without Confederate aid, Trujillo reluctantly agreed, and sent the requested troops over by September of 1943. By then, however, the situation at the front had worsened considerably, and despite his promises otherwise, Featherston would order the Dominican troops to frontline service in February of 1944, much to the chagrin of Trujillo.
This feeling of resentment was further worsened by repeated failures on the Confederates' part to continue promised shipments of oil and other resources to the country, in particular promises of deliveries of TARs and stovepipes. Confederate-Dominican relations steadily deteriorated throughout early 1944, and finally, after the fall of Atlanta, Trujillo would declare his intention of seeking peace with the Central Powers. By now the Dominican Republic was a shell of it's former self. Cut off from German, American, Dutch and Brazilian investment the country's economy quickly stagnated and, starting in mid 1942, entered into full on recession. Food shortages and other material deficiencies plagued the country. It was hoped by many Dominican officials that annexing key Haitian territory would help alleviate these problems, but this proved fruitless as the Confederates demanded a large cut of the pie for themselves and went back on many of their wartime supply promises.
In May of 1944 Trujillo would officially send a secret request to the US Secretary of State through his Foreign Office to surrender to the Americans. Despite some calls amongst some Democrats about the possibility of potentially shattering Confederate foreign relations, the majority opinion remained staunchly opposed to anything but unconditional surrender of any Entente nation, something Trujillo still refused to commit to. Instead, to pressure the dictator into surrendering unconditionally, the US made public Trujillo's request for an armistice, humiliating the man and instantly isolating him from Featherston and his more radical supporters. This, combined with the US bombing raid against Ciudad Trujillo [Santo Domingo] on May 18, would result in the Dominican Coup of June 1, 1944. On June 1 several army and police officers, upset over the direction of the war and Trujillo's failure as a leader, entered the dictator's residence and arrested him, proclaiming an end to the Dominican Party dictatorship and agreeing to unconditional surrender to the United States. The Dominican Republic was thus the first Entente nation in North America to surrender.
This prompted immediate reaction from Featherston, who ordered an all out attack against the country from Haiti in retribution for the Dominicans' "treachery." On June 6, 1944 several battalions of Confederate and Nicaraguan troops assaulted Dominican positions west of the newly renamed Santo Domingo, threatening the city with capture. Before that could happen, however, US air raids against Port-au-Prince and other targets in Confederate occupied Haiti forced the Entente coalition to fall back, and, on July 14, the official surrender of the CSA to the USA brought an end to all fighting on the island of Hispaniola.
After the war Trujillo would be brought before US, Haitian, and Dominican courts for trial. In December of 1944 he was found guilty on numerous accounts of crimes against humanity, crimes against the peace, among others, and on January 11, 1945 he was executed by a three nation member execution team in newly liberated Nassau, Bahamas, USA. He was the first Entente head of state to be executed for actions during the Second Great War.