LeBron James vs. Carmelo Anthony 

James' Notable Sneakers: Nike Zoom Generation, Nike Zoom LeBron II, Nike Air Max LeBron VII, Nike LeBron 8 V2, Nike LeBron 9, Elite PS 9, Nike Lebron X
Anthony's Notable Sneakers: Air Jordan XII PE, Air Jordan XIX, Air Jordan Melo 5.5, Air Jordan Melo M6, Air Jordan Melo M7, Air Jordan Melo M8, Air Jordan Melo M9  

Years: 2003 - 2012 

These two came into the league together, number one and three in the draft (sorry Darko) and have been gunning for the top spot in terms of rings and sneaker notoriety ever since. LeBron probably has the edge here since Melo's signature kicks have been suspect some years but his PE Jordan resume from his rookie campaign alone is one of the greatest in the game.