Not as a boast.
His statement was about the error of thinking of many in his position.
The first problem is the 'winning' as the thought process, the second problem is what is considered winning.
By many that think it is about winning, they don't look at the 'rules' they were told was winning, and get moved and directed by those rules, since much of some peoples life is about the winning, not seeing if what rules they were told was correct.
If you focus on the winning, you don't spend the time to think on what you are doing by the rules a person was told was winning.
Does that make sense, once you strive to win, then you no longer ask if the rules are what you want to follow in your life.
For instance, If you are out to win an argument then do you think of the methods to do that, or only the goal of getting what you were told was a win, might it be the methods are important to, and in that winning is not always the same for everyone, what many think is losing, can be winning for someone else.
Or, when you let someone define what a 'win' is, and you only care about winning, you are used by the person that defined those rules.
Jewel - You Were Meant For Me Official Music Video
http://www.youtube.com/watch?v=fGj77BrEgj4