The Legacy is an amazing watch that would look uber cool on Don's wrist. I Also agree about the Milenary, it's a fantastic watch, but the fact is that some people really suit sports watches, especially with tatoos and broken body parts. One 'traditional' watch that I think still looks chunky and sporty, and may well look cool on Don is the Lange Double Split. If you want an amazing movement take a look at that bad boy.
For now though this months watch should be the Legacy. Save the Lange for september. But it's Don's choice!