With the strength of the San Diego Padres' minor league system, the organization faces many key personnel decisions come this winter. At the top of the list is the Chase Headley situation. He doesn't hit free agency until 2015, but his contract status requires much attention.
Excluding arbitration contracts, the Padres only have $21 million committed to their 2013 roster (not listed in link: the Carlos Quentin and Huston Street extensions), but the club must weigh the potential long-term value of their assets with the possible trade packages that they might receive from interested parties.
This list contains the Padres players who I believe provide the most amount of trade value given their situation on the team.
The Padres' minor league system is top-heavy with Major League-ready, starting pitching prospects. Missing in 2013 will be Tim Stauffer (non-tender candidate after an elbow injury) and for at least half the season following Tommy John surgery, Joe Wieland.
The time has come to give rotation assignments to pitchers Robbie Erlin and Casey Kelly.
The 2013 staff would look like the following:
*Cory Luebke is expected back in San Diego in April/May
Clayton Richard has barely been above replacement-level this season—accumulating a 0.5 WAR—and he's been getting very lucky, as evidenced by his .260 BABIP (career average of .303). It would be wise for the organization to shop Richard this winter as a lefty starter capable of eating innings and being under team control through 2014.
The trade value of Yonder may never be higher than this winter, and it would behoove the club to determine his market value. His power does not seem to be well-suited to Petco (.120 ISO this year), but he still holds value as being under a team-friendly contract. The Padres could replace him at first base with power-hitting Triple-A first baseman, Matt Clark.
Having depth at pitching is always a good thing, but turning one pitcher into multiple is better. Luke Gregerson could be redundant given the pitching prospects chomping at the bit to be promoted, and while closer Huston Street's health is never a sure thing, Gregerson could bring back prospects who turn into MLB contributors, similar to the Mike Adams trade.
Signed to a very team-friendly extension this summer, Street could bring back a solid young hitter, similar to how Andrew Bailey brought Josh Reddick to the Oakland A's. Reddick has a 4.3 WAR in Oakland this season, almost two wins more than Street's best year in 2006 (2.4 WAR). The Padres should definitely shop Street at the Winter Meetings to closer-starved teams like the Chicago White Sox, New York Mets and Milwaukee Brewers.
Chase Headley doubles as the Padres' biggest trade asset and their most important positional player. Under control through the 2014 season, he could bring back a farm system-replenishing package of prospects or become the face of the franchise for the next several years. Any time a rebuilding organization has a player of massive value, it generally weighs the player's extension request against potential trade returns.
Last season, Padres GM Josh Byrnes, traded away the better of the Padres' two first base prospects, Anthony Rizzo, because of his trade value. Coupled with Jedd Gyorko's MLB readiness, I expect that the Padres' front office will actively seek a trade partner for Headley while simultaneously engaging the star fielder in exploratory contract negotiations.