T-Mac was right up there with Kobe and in fact, I think their career narratives could have flipped somewhat if they were in each other's position.
With T-Mac, those Lakers teams headed by Shaq would have still been dominant and championship teams. And before Bynum developed and Gasol arrived, Kobe had spent three seasons missing the playoffs and bouncing out in the first round, one in which, like McGrady, his team had been up 3 games to 1. With a McGradyesque teams around him, Kobe didn't have any more success than McGrady himself. He might not have experienced much playoff success had he not been lucky enough to have hall-of-fame teammates. The kind of player he can be, very shot happy and difficult to play with, he would have been ripe to label as a loser, fairly or unfairly.
McGrady's back and then knee injuries did him in. His back was flagged in pre-draft reports too so there was probably nothing he could have done to avoid his back problems. At his peak, he was far superior in seamlessly blending his scoring and playmaking than Kobe.