1. Will the Padres Find a Long Term Fit at Shortstop?
At the top of the Padres offseason to-do list, and really something that should have been a higher priority last offseason, is the gaping hole at shortstop. Despite revamping the entire outfield and half the infield, Preller and the Padres front office completely ignored the need at shortstop. The Padres rode through the season with mostly a combination of platoon players in Alexi Amarista and Clint Barmes, with Jedd Gyorko and Will Middlebrooks also getting some playing time there as well. With the disaster of 2015 clearly in the rearview mirror, shortstop absolutely needs to be the Padres biggest priority in either the offseason trade market or the free agent market.
While it seems fairly obvious that the Padres need to do something (really anything) to upgrade at shortstop for 2016, the question still remains on whether they will employ a short term fix or find a more long term fit. While the free-agent market has a dearth of talent at the shortstop position, with Ian Desmond being the only notable name, the Padres could find a fit at shortstop via a trade. The most likely fit appears to be the Chicago Cubs, who have a surplus of talent up the middle in Starlin Castro, Addison Russell and Javier Baez, and seek help in the pitching staff that the Padres are willing to give.
The Cubs and Padres discussed some things at the trade deadline last season and could extend those talks this offseason. The Padres could also explore trades of some of their more highly sought after players, such as Craig Kimbrel, and acquire a long-term shortstop prospect that way. It will be interesting to see if the Padres find a player who is ready next year, or if they instead find a short term option while they wait for something better to come along or a player to develop.