The most common and most likely answer to this crossword clue is the 3 plus 3 plus 2 plus 3 plus 4 letter word THE ART OF THE DEAL
I've seen this crossword clue in The Guardian
T
H
E
A
R
T
O
F
T
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D
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Buddy explains!
The straight part
We know that "Trump’s area of expertise?" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case trump’s area of expertise? = the art of the deal.The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.