Andy Pettitte will announce his retirement for the second time in his career. The question has to be addressed once again, does Pettitte deserve to enter Cooperstown? It might take some new age thinking in order to get Pettitte in to the hall of fame, but he's undoubtedly one of the better pitchers of this generation. 

Let's get it out of the way, the steroid accusations are definitely not in Pettitte's favor, but it's easy to forget that he was one of the players caught cheating. Pettitte's reputation hit rock bottom, but he was one of the few players to admit it and get it over with. If anything, Pettitte became an example for how to handle cheating in an age when steroid was at its highest. 

What are we supposed to do? Not acknowledge the best players of a generation that spans for over 30 years? We don't want cheaters next to guys like Babe Ruth or Hank Aaron, but there's something about Pettitte that sets him aside from guys like Mark McGwire, Jose Canseco and Alex Rodriguez. He's a guy who made a mistake, admitted he was wrong and did everything he could to get back the trust of his fans. 

Then there's the aspect of Pettitte's performance. Are 255 wins enough to get a pitcher into the Hall of Fame? 300 has always been the benchmark for pitching greatness in baseball, Greg Maddux and Tom Glavine are example for pitchers as they came up in the late 1980's, dominated their era and left baseball with over 300 wins. Those might be the last guys to do it now that baseball has become even more complicated with elaborate bullpens and specialists. 

Will 250 wins become the new benchmark for greatness? 

Pettitte is the current leader in wins among active pitchers. Looking at the guys oon that list and you quickly notice something specially about Pettitte. Tim Hudson is second with 205 and he's 37 years old and might have a hard time being effective after a devasting injury in New York over the summer. CC Sabathia has 204 career wins and he's 32. The other guys, Roy Halladay is 36 and not as effective anymore with 203, Bartolo Colon can't stay clean and he's 40 with 187 wins, Mark Buehrle is 34 with 185 wins, but he's very inconsistent. Derek Lowe is no longer pitching and he had 176 victories. From a realistic point of few. The only guy on the top active leaders with a chance at breaking 200 is Justin Verlander, who is currently 16th with 137 career wins. 

Now Verlander is considered one of the greatest from this generation, but will he get far beyond 200? Can he reach 250? Pettitte might be one of the last guys in the history of the game to win 250 games in his career. If MLB wants to acknowledge that he was a cheater and place him in the Hall of Fame, that's fine. But Pettitte is special because he represents various eras. 

Pettitte is from the school of pitching greatness. Pettitte is from an era where cheating was permitted. Pettitte is also one of the few players who showed class during one of the toughest periods in baseball. The sport is also to blame for turning its back on the steroid issue. Pettitte was a casualty, but he is one of the few who showed class during a trying point in his career.

If baseball wants class, Pettitte is not the best example, but he has persevered and he could be one of the last 250-game winners in the history of the game. It might take some time, but attention must be paid.