My family is Cuban (I was born in Ft. Lauderdale), initially supported Castro when he overthrew Batista (who was very corrupt), but then ended up fleeing the country and opposing Castro. My Grandfather (and most great uncles...etc., of that generation), where part of the Bay of Pigs debacle, were captured and sent to prison. There are always two sides to every story, and I always try to look at things in a detached/unbiased way (my grandfather owned the largest department store in Havana, so while he lost everything, many of the poor people gained something). A few thoughts I have on Castro:

1. Obviously a very smart man, and very brave for making multiple attempts to overthrow a corrupt regime (was exiled for a previous attempt when he and Raul threw together their "raiding party".
2. Extremely charismatic and a phenomenal public speaker.
3. Completely full of shit and 100% committed to nothing but his own power. Read Che's story and see the hypocrisy of Castro once in power. Che was a lot of things, but that man was no hypocrite and a true believer in Communism. Castro was an opportunist.
4. Hard to say Castro was successful as a leader at all looking at the conditions in Cuba today. I can't see anyone saying Cuba flourished or had great conditions at any point under his reign.