Fidel Castro

With the passage of yet another undemocratic communist dictator, do not make him out to be better than he was. Castro was a monster who restricted freedom of the press and religion in his totalitarian state which until 2013 was the only country in the Americas which limited the ability of its citizens to leave. He also persecuted gays and admitted it willingly. When it comes to his policies, he was far more like Kim Jong Un than Willi Brandt which a lot of right wingers are going to make him out to be today (if they only knew who Willi was). Merely having public health care does not make a country free. Praising Castro is pissing on the people of Cuba. I hope the monster had a painful death for his crimes against humanity. 

Burn in hell you monster.

If you consider yourself left-wing than you have to consider yourself a liberal (communist thought and practice has not respect for human rights, and the largest body count of any ideology in history), then remember him for who he was and his multiple atrocities against the people of Cuba. Cuba has the worst Freedom of the Press in the Americas, bans gay marriage, their government regularly tortures prisoners, and has no freedom of assembly. Granted, the United States is not perfect either, and also has large problems with prisons and the current attacks on Standing Rock are a massive violation of the rights of the Sioux, both under treaty and the Bill of Rights. This is why we, like every other country in the world, do not have a perfect score on any broad freedom metric. But when political scientists analyze both Cuba and the United States there is no doubt that Cuba is far less democratic and free than the United States. This is a system which Fidel Castro built, and it is a monstrosity against the people.

If you want a hero to idolize, than there are good people who are worth remembering and living up to. German Chancellors Konrad Adenauer, Helmut Schmidt, and Willi Brandt built the system of Germany based on liberal thought and Germany is now beats the United States on every freedom metric except gay rights where the USA beats Germany. Willi dissented from the Nazis during the Third Reich at great personal risk before being our greatest Chancellor. Pierre Trudeau built Canada's respect for Quebecois culture and Medicare and was a great man. Clement Attlee built the British Welfare State and was the greatest Prime Minister they ever had, reversing Labour's indefensible policy of appeasement and led decolonization. Lyndon Baines Johnson signed most of our civil rights laws and worked hard to try to get us out of Vietnam while leading a booming economy. Bob Hawke led Australia's economy through the turbulent 80s with skill which no other leader in the world had at the time, introduced medicare, and made their social policy more liberal. Nelson Mandela led South Africa to freedom.

There are great people in history who stood against dictatorship and built freedom and prosperity. Remember them for who they are and remember that Fidel Castro was a man who all of them actively opposed for that reason.

Relations with Cuba

I have thought of the issue with Cuba and wrote the following comparison that makes the answer apparent to me:

The embargo on Cuba is based on the old fear of America against Communism. The laws Cuba has that are the most draconian are drugs, the trade must be stopped in the world, politics, it is a Socialist state afterall, and porn, it is a Roman Catholic society. The first and third are things that are prosecuted in America, and the second will definitely change someday. If Cuba had visitors from America and were able to visit America, they could bring back our ideas to their home country the same way President Saakashvili did in Georgia. That would improve the lives of Cubans. The United States would not be damaged either, because the tourists from Cuba would bring in money as much as money is brought in to Cuba. In fact, the increase in tourism would create a boom that would benefit our economy! It would be beneficial to both countries. It would make Cuba an even safer place to travel.

    Another factor is that after The United States began relations with China, they got more money in their economy and started to build their country up to the point where today their trade has made them one of the most powerful states in the world. The problem with Cuba is they don't have enough trade for the people to make enough income to improve their standards of living. Allowing Cubans to travel between America and Cuba will make the amount of information available in Cuba higher, which will make the people able to stand up to information restrictions through travel. It would continue to allow Cuban dissidents to migrate to America for political asylum, and the draconian laws will decrease and wither, just like China. In fact, it would be faster because Cuba is only 90 miles from Miami, a distance shorter than from New York to Washington, DC!