Is he deportable?
Depends on the documents.. but in my opinion, likely yes.
Can he still get his citizenship?
50-50... you would need an experienced immigration attorney's help to explain why you should be allowed to live in US and become US citizen.
Will the previous encounters with the law be overlooked because they are more than 3 years old?
No.. You should always be honest with USCIS regarding all:
# Arrests (including those by police, Immigration Officers, and other Federal Agents);
# convictions (even if they have been expunged); and
# crimes you have committed for which you were not arrested or
# convicted.
Even if you have committed a minor crime, USCIS may deny your application if you do not disclose the incident. It is extremely important that you tell them about any arrest even if someone else has advised you that you are not required to do so.
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