It depends on the charges and how immigration gets involved, but here is how it usually plays out.
If your boyfriend has no legal status, there are typically two separate systems involved:
What happens first:
He will go through the normal criminal process:
If the charge is minor and this is truly his first arrest, he may:
Where immigration comes in:
If immigration places a detainer (ICE hold) on him:
After that:
Important points:
Bottom line
If he has no papers, there is a strong chance immigration will get involved at some point. Whether he does jail time first depends on the charge, but deportation is a very real possibility once the case is finished or if an ICE hold is placed.