Phillies GM Ruben Amaro, Jr. has quite a bit on his plate this offseason. Having already signed a veteran closer in Jonathan Papelbon, Amaro has one less obligation to worry about.
However, he's still got a few more positions to settle: shortstop, another pinch hitter or two, and a left-handed reliever. Amaro could also look to sign a starting left fielder if he feels that John Mayberry Jr. can't get the job done, or he could sign another starting pitcher if he feels that the rotation is lacking.
The offseason is still just beginning. With the kickoff of the annual Winter Meetings next week in Dallas, there will be signings galore, and most of the remaining free agents will have found their new (or former) team.
The biggest question is not who Amaro could sign, but what could prevent him from doing so for specific players. Signing higher profile free agents, such as Jimmy Rollins, will have more obstacles. Others may have a slight obstacle. Nevertheless, Amaro will have to work around any given roadblocks, and he'll have to settle with the fact that not every deal he wants to do will get done.
But what sorts of roadblocks could persist? In this slideshow, we'll discuss some of the potential targets or target positions for which Amaro may pursue players and what could prevent him from getting who he wants.