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> だから僕は、たまに彼を昔の僕と重ねていた。

> 重ねて:  
>  1. 同じ行為・事態をもう一度繰り返すさま。再び。文章語で、多く手紙や公式の発言に用いる。 「 －要望する」  
>  2. この次。今後。 「 －は泥鰌（どじよう）にてもあれ、鮠（はえ）にても候へ必ず持つて伺候致さうずる／狂言・鱸庖丁」  
>  ([Source](https://www.weblio.jp/content/%E9%87%8D%E3%81%AD%E3%81%A6))

The context is the narrator finds his classmate quite similar to his former
self. So point 1 fits the above sentence.

Could I translate it as follows:

> That's why I sometimes saw my former self again in him.

Thank you for the guidance.
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translation
The translation of 重ねていた
This 重ねて is a simple te-form of the verb 重ねる, followed by いた that makes the
past-progressive form (expresses a past habitual action in this case). Or you
can say this is the past-teiru-form of 重ねる. Here, 重ねる means "to identify with
someone" or "to project someone into ～".

> だから僕は、たまに彼を昔の僕と重ねていた。  
>  That's why I sometimes projected him into my past self.

As you have cited, 重ねて also has a lexicalized usage ("once again"), but you
can forget it for now.
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> だから僕は、たまに彼を昔の僕と **重ねて** いた。

重ねて in 重ねていた is not an adverb but the te-form of the verb 重ねる.

Here (～を‥と/に)重ねる means "to identify ~~ with‥" "to see ~~ in‥" (≂重ね合わせる), hence
the translation:

> That's why I sometimes **saw my former self in him**.
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