"I'm a very modest person. But I'm also extremely confident. And if you put me in the situation or in the moment, I'm gonna have some swagger, I'm gonna have some cockiness"

Drew Brees is conveying that he is a simple individual, however also has a lot of self-assurance. He is suggesting that when he remains in a situation or minute that needs him to be positive, he will have a certain level of swagger and cockiness. This is likely a reference to his success as a professional football gamer, where he has actually needed to be positive in order to prosper. He is most likely suggesting that he is able to stabilize his humility with his confidence, and that he is able to make use of his confidence when needed. This quote is a testimony to his ability to stay humble while likewise having the self-assurance to be successful in tight spots.