The latter half of the 2000s saw the Philadelphia Phillies and Florida Marlins headed in diverging directions. Between 2005-2009, Philadelphia’s 447 wins and .552 winning percentage ranked 4th and 5th, respectively, among MLB teams. The Phils captured two NL pennants, including a World Series title in 2008. As for the Marlins, they finished 18th and 19th in those categories, winning 403 games, which was not even half of their games (.498 winning percentage).
With news of longtime Marlins killer Ryan Zimmerman announcing his retirement earlier this week, another Ryan with NL East ties, Ryan Howard, comes to mind.