The prior removal will be a complication in requesting recent status or the immigrant visa. I suggest that you have a private consultation with an experienced immigration attorney to review your case.
You need to provide more details such as the basis for the deportation so we can determine the bar; how long ago he was deported - perhaps he's already cured the bar. Please consult with an immigration attorney bringing as many details as possible. If there is a criminal history, bring a certified court record disposition for each conviction and bring a copy of the deportation order.
If once, probably yes, depending on whether a waiver would be granted.
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