I'm about obama's age. I had to register with Selective Service as a precondition of receiving financial aid for college (among other reasons). If he failed to register or registered falsey, all his financial aid would have been obtained fraudulently.
He is disqualified for any federal job, based on not registering:
Registration for Selective Service is also required for various federal programs and benefits, including student loans (such as FAFSA), job training, federal employment, and naturalization.