That's how much it's worth to me to see Roy beat him, and that way, if he loses, I'll at least make some $$$ in the process of grieving. Win-win.
You are just like Jimmy "The Greek". He used to say he would do that on big events that had his favorite athlete or team playing. I think you and Jimmy are on to something.
I always do that: bet against the guy I really want to win. It's win/win that way. But, seriously, if you've got the jack to lay down five grand on a fight, you shouldn't be greiving about anything, ever!
I don't like betting on boxing matches than I care about. Spoils the fight, I want to enjoy it for the occasion- not because I have money on it. I was gutted for a whole day when Hatton lost to Mayweather, but how I felt after seeing Hatton getting beaten up by Mayweather after fighting his heart out made the fight more 'great' and memorable.