It's funny because I've had this exact conversation with my older brother, about him and I. He maxes out at about 103-104 club head speed, and I max out around 116. Yet there are plenty of situations where his well struck tee shot is out there even with, just behind or just past my drive. He pretty much maximized his potential distance (center strikes, plenty of loft, low spin, slight draw) on pretty much every drive, where I tend to leave some on the table most drives (offcenter strike, slight fade, etc.) Granted when I center punch one, I'm 30-40yds past him, but that's a rare occasion.
Bottom line is there are plenty of situations where a slower swing speed player can outdrive someone faster.
Bottom line is there are plenty of situations where a slower swing speed player can outdrive someone faster.