Parenting & Family Quote by Drew Brees

There is a particular kind of flex that only works when it pretends it is apologizing, and Drew Brees nails it here. He opens with “I know,” the classic empathy cue, then immediately pivots into the real payload: “how many times I beat him.” The sentence is built like a grin you can hear. It’s not hostile; it’s a carefully calibrated humblebrag that keeps Brees likable while still letting him claim the alpha memory in a rivalry people didn’t even know existed.

The name-drop does heavy cultural work. Andy Roddick isn’t just “a friend” or “a guy”; he’s a recognizable champion, which turns a childhood anecdote into a status multiplier. Beating Roddick “when we were kids” offers a safe zone where egos can spar without threatening adult accomplishments. It’s a way of saying: I respect what he became, but I was there first. Nostalgia becomes a competitive arena.

Subtextually, Brees is also performing the athlete’s version of authenticity: the idea that greatness is legible early, that elites can trace their destiny back to playground scorekeeping. It plays well in a sports media culture that loves origin stories and cross-sport mythology. And it humanizes both men. Roddick gets to be the long-suffering friend; Brees gets to be the guy who still counts the wins, because of course he does. Competitive people don’t stop competing. They just learn to laugh while doing it.