Realistically? Pretty tough--students have to show that they do not have immigrant intent, and that means being able to prove that you will come the US, study, and go home. That's hard to do when you are on record saying you are so afraid to go home that you wnat to apply for asylum.
It sounds like he was paroled in for his asylum case? If so, and if he is not successful, hopefully he can compelte his degree while that process is going on. An H-1B visa for a professional worker does not carry the requirement to show nonimmigrant intent. If you leave on VD and have an H-1B to come back to, that might be an option. This is not "do it yourself" territory--go see a good immigration lawyer for help.
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To be perfectly honest, his chances are next to zero (0). His best chance of ever returning to the U.S. is if in the future a U.S. citizen fiancee will file a fiancee petition or a K-3 after marriage, on his behalf.
Behar Intl. Counsel 619.234.5962 Kindly be advised that the answer above is only general in nature cannot be construed as legal advice, given that not enough facts are known. It is your responsibility to retain a lawyer to analyze the facts specific to your particular situation in order to give you specific advice. Specific answers will require cognizance of all pertinent facts about your case. Any answers offered on Avvo are of a general nature only, and are not meant to create an attorney-client relationship.