This one is easy. I love “assassination” because it has two asses. I learned this from a kid named Amir in the sixth grade, and I cannot write this word without remembering that wonderful moment when I realized I was writing “ass” on my spelling test.
An interesting fact about this word, it actually comes originally from Arabic, and shares a common heritage with “hashish”. The “hashishiyyin” were a group of Arabs known for eating hashish and murdering opponents. The word was later anglicized after spending some time in the French and Italian laundry.
Also, I’m going to go out on a limb and suggest that the online etymology dictionary is full of shit on this one.
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