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Antony had a great mind and was gifted in the art of manuevers. Brutus underestimated Antony because he fely him pleasure loving and unable to take life seriously. He never thought about the Antony who'd manipulated warfare and was a gifted tactician. and perceived him as a person who didn't always take life seriously. He also underestimated Antony's ability as an orator. The speech after Caesar's funeral did more than all other tactics put together to being about the beginning of Brutus' fall.