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For those of us living in the American South, hurricanes are a normal part of life. Every year, we have a hurricane season, which goes from June to November. During that time, we keep a close eye on the weather because any little storm that develops in the Caribbean, can turn into a major hurricane and devastate our coasts. And not just our coasts; a hurricane can travel in any direction, crossing several states and leaving a trail of destruction in its wake. That was the case in 2012, when Hurricane Sandy worked its way from the Caribbean all the way up to New York causing unimaginable destruction and death.
Caribbean | This word can be pronounced [kʰǝrɪ́biyɛn] or [kʰæ̀:rǝbíyɛn].
in its wake | A wake is the trail of water that you see behind a boat as it moves along. Figuratively, the phrase in [someone's/something]'s wake is used to refer to what they LEAVE BEHIND them; what follows them — usually not something good. For instance, in this case, hurricanes are known for leaving destruction in their wake, i.e. BEHIND them after they pass.
that was the case | The phrase the case simply means that's precisely what was happening, what happened in reference to a situation you've just described.
to keep a (close) eye on someone or something means to watch them carefully; for example, if you want to make sure nothing bad happens or in order to be a few steps ahead of something potentially dangerous. That’s what it means in this sentence — we watch storms very carefully so that we won't be taken by surprise if they turn into hurricanes and start moving towards us.
to work one's way [somewhere]This phrase means to gradually make progress towards a destination or goal. It has nothing to do with work, even though it may involved a little struggle, discipline and dedication, but it basically refers to just moving at a gradual pace, not necessarily fast, but steady. And not just in the physical sense! someone learning a new language can work their way through a novel by stopping to look up words in the dictionary, looking up grammar points, etc. and gradually and steadily progress through the book. "With the help of a dictionary, I worked my way through War and Peace, in Russian, in just under a year."
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