Those who have ruled Cuba since the Spanish-American War have had different types of governments and ruled in different ways.
In the early years, the United States essentially ran Cuba. Under the control of a military government, the island had no democracy. Dissent was not really an issue, since the United States would change the situation when it wanted to, and protesting wasn't going to yield much. The Platt Amendment also insured the US could continue to intervene, as it did.
After that, elections took place. The early Cuban Government was corrupt and widely criticized for so being. Many elections were conducted improperly; mainly candidates gained victory through fraudulent means.
Further, much of Cuba was owned by foreigners, mainly from Spain and the U.S. By 1909, only 31% of sugar mills were Cuban-owned.
The Presidents of Cuba often amassed great fortunes during their terms in office. Though democracy seemed ineffective, it existed in Cuba until Machado's regime.
Machado forbid the creation of new political parties. He murdered opponents, notably Julio Antonio Mella. Then, he held a constitutional convention that gave him another term as President without having to be reelected.
In the Revolution of 1933, Machado was overthrown. Those who took power were quickly displaced through a revolt by sergeants.
From here, Fulgencio Batista became the most important man in Cuba. There were elections, but Batista usually controlled the Presidents. The United States was well treated during this period, and American companies were able to freely profit in Cuba.
This appeared to change significantly with the election of Ramón Grau. Grau had refused the Platt Amendment and claimed to put the people were in power. Soon however, his government became friendly with the US and highly corrupt.
As a result, little changed throughout the years until Batista returned to power. For the first time, people were rounded up and killed by the President's thugs. Batista was very friendly with both US companies and the American Mafia, both of which prospered in Cuba. Eventually, however, various opposition groups forced Batista to flee Cuba. Among these groups, Fidel Castro's was able to gain power.
Castro's government immediately promised to hold elections, but didn't until years later. The government was neither corrupt nor friendly with foreign businessmen, like nearly many before it.
The future of Cuba is far from clear. The Communist government could remain in power. Another alternative is that a right wing government composed of anti-Castro exiles would take power. This would mean a return to strong relations with the United States and its businesses.