Giving a direct a 2nd chance to make the right choice? Ticking off the boss...

My boss (owner of small company) recently asked if we could send one of my directs on an emergency out of town trip 5 days before Christmas.  This trip was to a remote location, accessible by bush plane (in short - crummy duty).  I said sure and since I was out of the office and the boss and direct were 20 feet away from each other, the boss asked if I'd like him to go talk to the direct about it.  I said sure.

The boss asked the direct if he could step up and make the trip and the direct was quite honest in his response "Can we even get plane tickets out there? What is the weather like out there?  Can we get access to the facility that I need to work in?  Do we have to go out there or could we troubleshoot over the phone? etc..."  The boss then got irritated and told him he would find someone else.  

The next person the boss asked, "Joe", responded with "Sure.  Let me know the details."

The boss called me and told me that he had found someone else and that he was very disappointed with my directs response.  This was really disappointing to me as well -  I had very recently gone to bat for the direct to receive a nice end of year bonus.

I called the direct an hour later and asked him what had happened.  He responded that it sounded like a recipe for getting stuck over Christmas.  I asked him if he knew what the plan was now.  He indicated that "Joe" was going to go out for the emergency trip.  I asked him if he thought it was better that "Joe" got stuck over Christmas rather than him.  He paused and responded "No"  I then let that sink in with some uncomfortable silence to which he responded with "I'll go"  I told him great and suggested that he speak with the boss and possibly apologize.

When I spoke to the boss the next day, he asked if I had spoken to the direct.  I told him that I had.  He was upset that I had spoken to him as he wanted the direct to come to the decision to go out on his own.  I indicated that my experience was that the direct would not have come to that decision without coaching.  The boss was concerned about what this incident showed about the character of the direct, that character can't be coached, that this was obviously a "B" level guy that we are dealing with, etc.  And he was pretty ticked at me for coaching him to go since we were sending out a guy that didn't want to be there (would he complete the work, deal well with customer, etc.)

So, now I'm in a situation in which a guy that is one of the best technical people on my team, is very conscientious about bringing projects in under budget, is never late, and generally has a great attitude, is viewed by the boss as sub-par.

Any suggestions?