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The Torah (Genesis 32:4) says that Jacob sends "malachim" to Esau. Rashi there interprets "malachim" (commonly referring to messengers, or angels) as "real malachim" ("מלאכים ממש"). I've also heard from various Rabbis that this means that Jacob actually sent angels to Esau!

To the best of my understanding, the term "malachim" literally means "messengers", and is a term that is borrowed to refer to angels, who are "heavenly messengers".

Is it possible that when Rashi writes "real malachim", he is actually trying to say "real messengers", since "malachim" literally means messengers?

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Very interesting question! However, Rashi is relying on the Midrash in Bereshit Raba (75:4):

מלאכים - אלו שלוחי בשר ודם. ורבנן אמרי מלאכים ממש.

Rashi, citing Rabanan, comments that the meaning is actual angels as opposed to messengers.

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