No conversion from Roth to Traditional.
If he cashes out the Roth IRA, there may be a penalty. But there's also an itemized deduction (2% miscellaneous) for the amount lost. (Sounds like he's high income, so 2% AGI limitation may make deduction worthless)
If he's single, try the personals:
Single man seeks woman with large capital loss carryforward, object matrimony (ASAP!). Looks and personality unimportant.