Federal agencies, like the military, do not have to adhere to Florida laws involving expungement. Even though the actual records held by local law enforcement and the courts will be destroyed once the arrest is expunged, it will still show up on the FBI's NCIC "Rap Sheet". When a record is expunged an agency which entitled to the NCIC report will only receive your physical description information and a general statement saying that criminal history information has been expunged, but will be unable to receive the details. There are several agencies in Florida which are exempt from the expunction rules, such as the Florida Bar, law enforcement, prosecutors and the court if you are arrested again and any job that involves contact with children, elderly or disabled adults under a State contract, to name a few. In the case of a Federal agency, such as the Department of Defense, you should expect that they will see your NCIC Rap Sheet and ask you about the details of the expunged case. Certainly, if you are seeking a job with the military that requires a security clearance or is involved in law enforcement or port security, you should expect to have to reveal and explain your past offenses. For these types of exempt agencies, you should go ahead and inform them of your criminal history up front, so that they do not reject you outright for being untruthful to them. (Other non-exempt employers and agencies do not have a right to the NCIC report and you are entitled, under Florida law, to deny that you ever had the charge, once it is expunged or sealed). It is always a good idea if you get a case expunged to first obtain certified copies of the police report and court file for your own records. That way, after the official records have been destroyed, you will be able to show the certified copies of the case records to the exempt agency in order to satisfy their need to investigate you thoroughly. For the military, you can get more particular information on the requirements for the specialty you plan to go into from a recruiter. An experienced criminal law attorney can assist you in obtaining an expunction or sealing and in getting the certified records for your file.
Legal disclaimer: this response is not intended to create any attorney-client relationship and is based on the limited facts given and should not be relied on as legal advice. It is recommended that you consult with an attorney before taking any action based on the foregoing statements.
Read the application very carefully and see what it asks for. Does it say, "Have you ever been arrested?" or "Have you ever been convicted of a crime?" The way the question is asked is very important as it may change your friend's answer.
The military will be able to see his record. If the records were expunged that means that the charges were either never filed, charges were dismissed or he went to trial and won. If it is asked, I would recommend that he disclose his arrest on the military application. He will always be able to explain the circumstances of the arrest.