Though popular hatred against Heureaux was strong on account of his tyrannical conduct and his attempts to compel the circulation of a large issue of inconvertible bank notes with which he flooded the country, the fear in which he was held prevented any general uprising. There were many, however, among them Horacio Vasquez, who never ceased conspiring against the dictator. When it became known that Heureaux was resolved to bring about Vasquez' death, Ramon Caceres, a cousin of Vasquez, and other members of the Vasquez clan, were drawn into the conspiracies. The father of Caceres, once vice-president under Baez, had been killed, it is said, by order of Heureaux. In July, 1899, when Heureaux prepared for a trip through the Cibao, he was informed of a plot to kill him on the way. When he arrived in Moca he thought that no danger awaited him there, as he expected that if any attack were to be made on him it would be at some solitary portion of the road and not in a town in broad daylight. When about to leave Moca on July 26, 1899, he ordered the governor of the province to arrest Caceres and his companions. Caceres was informed of the order by the secretary of the governor, who was his friend, and knowing that the arrest would probably be followed by an execution, with several companions he repaired to a store where Heureaux was talking with the proprietor, the provincial treasurer. As soon as Heureaux appeared in the doorway Caceres began to shoot, and the other conspirators continued firing, although the first shot had been fatal. Heureaux before falling drew his revolver and returned the fire, but the darkness of death clouded his vision and the shots went wild, one of them, however, killing a beggar to whom he had a few moments before given alms. Caceres and his companions fled to the mountains, and the body of Heureaux was taken to Santiago, where it was afterwards interred in the cathedral. Juan Wenceslao Figuereo, vice-president of the Republic, an aged negro, succeeded to the presidency.

The death of Heureaux precipitated a revolution headed by General Horacio Vasquez. President Figuereo made no resistance, but at the end of August resigned, together with his cabinet, first designating a committee of citizens to administer affairs until the arrival of Vasquez, who entered the capital on September 5, 1899, and became the head of the provisional government. Jimenez in the meantime hastened to the country and was everywhere received with rejoicing. The two leaders arranged that Jimenez should become president and Vasquez vice-president, and an election was held on October 20, by which this result was attained, the inauguration taking place November 20, 1899. Ramon Caceres, the slayer of Heureaux, was made governor of Santiago and delegate of the government in the Cibao.

The Jimenez administration was the reaction of that of Heureaux. It deserved, more than any the Republic had had up to that time, the name of civil and constitutional government. The executive was not absolute, as in the time of Heureaux, nor were there sanguinary executions. Almost too little restraint was exercised, and the press, so long muzzled, began to convert its liberty into license. Jimenez, too, was so good-hearted that at times he yielded to importunities which had better been resisted. The financial problems left by the Heureaux administration caused considerable trouble and though the waste of the public revenues was curtailed, large sums were still absorbed in the payment of revolutionary claims and of pensions for local military chiefs.

Jealousies soon ripened between Jimenez and Vasquez, who was known to long for the presidency and had only temporarily laid aside his aspirations on account of the overwhelming popularity of Jimenez. Each of the chiefs collected a group of friends about him and in this way originated the still existing political parties, Jimenistas and Horacistas, the respective followers of Jimenez and Horacio Vasquez. Several minor uprisings occurred but were suppressed by the government. In the beginning of 1902 the Dominican Congress, which was composed largely of Vasquez' friends, considered the advisability of impeaching President Jimenez on account of the financial transactions of the administration, and a vote of censure was finally passed. Jimenez believed Vasquez at the bottom of the agitation and endeavored to have the municipalities protest against the action of Congress. Rumors became current that Jimenez intended to imprison his vice-president and thus insure his own reelection. Vasquez, urged on by his friends, therefore started a revolution in the Cibao, and after a fight in San Carlos and a four days' siege of the capital entered Santo Domingo City on May 2, 1902, and became president of a provisional government. Jimenez sought refuge in the French consulate and embarked for Porto Rico a few days later.

General Horacio Vasquez was born in Moca and was a ranchman, merchant and planter. He possessed military capacity and took a minor part in several revolutions. At first a friend of Heureaux, he afterwards became one of his bitterest enemies, and for a number of years lived as an exile in Cuba and Porto Rico, returning to Moca shortly before the death of Heureaux to remain in retirement on his plantation. The Vasquez administration had as much difficulty with financial matters as that of his predecessor, but the president had little opportunity to show what he could do. Local outbreaks began in Monte Cristi and became general in October, 1902. Disturbances continued until March 24, 1903, when, during the absence of President Vasquez in the Cibao, the political prisoners in the fort of Santo Domingo City, through connivance with the general in charge, broke out, took the fort, liberated the convicts, threw the city into a panic with a continued fusillade, and proclaimed a revolution. They were for the most part Jimenistas and "Lilicistas," or members of the old Heureaux party, and their candidate for the presidency would probably have been Jimenez; but in Jimenez' absence the presidency was offered to Figuereo and others, who declined, and was finally accepted by Alejandro Woss y Gil, who had only the week before been liberated from the same political prison.

General Vasquez returned with an army, arriving before Santo Domingo City at the end of March. The ensuing siege was one long battle, during which a portion of the suburban town of San Carlos was destroyed by fire. On April 18, 1903, Generals Alvarez and Cordero, the best generals of the besiegers, made a violent attack on the city and effected an entrance, but fighting continued in the streets and these leaders and most of the storming party were killed. Vasquez thereupon fled to Santiago, resigned his post, and left the country for Cuba. On the triumph of his party a year later, he returned to Santo Domingo and retired to his plantation in Moca.

Woss y Gil, who thus became president of the provisional government, called a session of Congress and by appointments favorable to his interests so intrenched himself that his continuance as president became assured. Jimenez, who arrived shortly after, advanced the claim that he was still president de jure, since the constitutional term of four years for which he had been elected had not expired, and he denominated the Vasquez government a temporary and illegal usurpation of power. In his efforts to regain office he sent his friend Eugenio Deschamps to treat with Gil, but Deschamps, seeing Gil obdurate, made an agreement by which Woss y Gil was to become president and Deschamps vice-president, Jimenez was obliged to yield to the inevitable and returned to Porto Rico in the hope of eventually succeeding Woss y Gil. An election was held in which Woss y Gil and Deschamps were the only candidates and on June 20, 1903, they were inaugurated.

In General Alejandro Woss y Gil the Republic had a very talented man as president. Born in Seibo, he had entered politics in his youth, and became a friend and follower of Heureaux. At times he was governor of a province, later for a long period Dominican consul at New York, and from 1885 to 1887 president of the Republic. He had received a good education and traveled extensively, spoke several modern languages, had some knowledge of the classic languages, and was a poet, musician and writer.

Unfortunately the talents of Woss y Gil did not extend to the securing of an honest and efficient administration. The ministers appointed by him were exceedingly injudicious selections, and a carnival of fraud and dishonesty was soon in progress. Discontent grew general, and by the end of October, 1903, General Carlos F. Morales, governor of Puerto Plata, raised the standard of revolt and his troops marched on the capital. The revolution was supported by both parties, the Jimenistas and Horacistas, and was known as the "war of the union." Morales, the leader of the insurrection, had been a follower of Jimenez and favored the aspirations of the latter to the extent even of sending requests to Jimenez to come to Santo Domingo at once. The siege of Santo Domingo City lasted for about three weeks. On November 24, 1903, Woss y Gil, finding himself vanquished, permitted Morales' troops to enter the city and sought refuge in the British consulate. Three days later a German man-of-war carried him to Porto Rico, and he later continued to Cuba, where he long resided in the city of Santiago.

For a short time a tripartite revolution was in progress, the supporters of Woss y Gil, Horacio Vasquez and Jimenez fighting in different parts of the country. Morales, on entering Santo Domingo, became president of the provisional government. The new governors of the Cibao were Jimenistas, but most of the appointments Morales made in the south were Horacistas, and it began to be suspected among the Jimenez followers that he had designs on the presidency. When Jimenez arrived in Santiago he realized that his ambitions were again endangered and he and his friends grew restless. On December 6, 1903, Jimenez fled from Santiago to Monte Cristi, claiming that Morales had sent a troop of fifty men to assassinate him.