It's not like he's losing every match he plays.
He actually consistently wins matches. Despite the occasional first-round-loss at a challenger, on an average week he wins more matches than he loses. If you look at http://www.atpworldtour.com/Tennis/P...oung.aspx?t=pa
and include challengers and qualies, his record is like 35-16. It's just that he plays mostly on the challenger level, and there he's near the upper echelon of challenger players (so he gets wins) but he's near the lower echelon of ATP-tour-level players, so when we see him at ATP-level events he mostly loses. His record at the ATP level for this year is 6-9, which means that at below-ATP-level events his record is, I believe 29-7.
He's settled in to his career. It looks like he'll be one of those guys that permanently stays in the just-below-100 range, with occasional forays into the top 100 when he gets a few good wins. It's not a glamorous career by any means, but it's enough to make a living.
I don't feel sorry for him. I'm not jealous of him either, but he should do okay. He's not going to live up to his hype as a great player by any means, but it's not like I feel sorry for the plenty of other players that have careers like that. Do you also feel sorry for Michael Russell, or George Bastl, or the many guys at the level of Russell and Bastl who *don't* have that one extra big moment