Sometimes the oldest guy in the sport is also the coolest.
And so it goes for the select group of individuals that are laid out before you. They still walk around like they own the place, and we love it.
We aren't working with a strict set of criteria here. For age, any former athlete, coach or analyst who exudes as much wisdom as they do panache will be considered.
As for "cool," any old guy who would mandate you buying him a beer the second you see him in public qualifies.
Of course, this is a work in progress that demands your help. I know you have some idea of cool guys and thoughts on the ones provided. Please, supply your completely reasoned and well-thought out points in the section below.
Now, let's get classy with it.