Yeah, it's definitely naked so I know there's a credit-risk, but we work together and I know he's good for all but the most extreme outcomes.  Still I'm tempted to help him along by capping his downside (maybe making the deal a call-spread $1000 vs. $2000 or something - i.e. I sell him back a $2000 call), though it's a shame to lose the convexity to the upside.