El primero de ellos fue un maestro de pintar panderos, al que "le" ayudaba preparándo"le" los colores.
In this sentence, why are there two le?
And what those le designate?
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The first is a case of "leísmo" (overuse of "le") used in many countries. Since that first "le" functions as direct object, it should be "lo", not "le":
... al que lo ayudaba ...
The second "le" is an indirect object.
He helped him (direct object) by preparing him (indirect object) the colors.
Lo (le, in countries where "leísmo" is used) ayudaba preparándole los colores.