Winning is always fun, who could ever get to the point of not enjoying it?
Sure it is but it's not always that fun to win by, say, 2 minutes. It's more fun to win a well fought race than it is to run away from everyone. Running away from the competition can definitely feel like a hollow victory. I've been in some races where it didn't even really feel like a race because I didn't even see anyone after the second step and didn't have anyone near me after 50 yards.
That was actually covered by earlier comments in the message post. In this day and age, one has oneself to thank for that unless one is too dense to figure out how to research past results for the race. 8)