Jason McLeod is a Highlander from the clan McLeod. No wait, no he is not. That was MacLeod anyway. Jason McLeod is the current Senior Vice President, Player Development and Amateur Scouting for the Chicago Cubs. He used to have a similar role for the Padres when Jed Hoyer was the General Manager from 2009-2011, but when Hoyer bolted for the Cubs McLeod went with him. Recently, the good guys over at Baseball Prospectus wrote about all the top GM candidates and here is what they said about McLeod:
Skill set: During his tenure with the Cubs, McLeod has played a major role in turning over an organization that was thin on minor-league talent, augmenting the infield talent that was present before his tenure with Kris Bryant and Albert Almora. He also has a keen eye for what can be considered undervalued pitching, as the Cubs have enjoyed pitching success by acquiring "project" arms whose value has increased with the club—most recently Jake Arrieta and Jason Hammel. His resume shows that he has an eye for talent and would be a good fit for a larger role in any front office.
I think the points in McLeod's favor when it comes to being the next GM of the Padres are two-fold. One, he is already familiar with some of the organization. That does not just include players he helped draft, but also scouting personnel that he helped hire. Some of the processes for scouting and player development might still be kicking around or at least are something that some of the current staff is familiar with. The second key factor is that "Player Development" aspect. Most people recognize that the Padres will have to develop their own talent in order to be successful and the new GM would have an advantage if that is his strong suit. McLeod would bring in the expertise needed to get the farm system back on track and right the ship of some of the current prospects that are not on a path to hit their ceilings.
The Player Development background can also help on another front. While McLeod has never been a GM before and therefor may lack the skills of the wheeler-dealer GM, having a good system for player development that tracks which prospects and major leaguers are progressing well or stalling out gives the GM extra insight into who should be traded and when. If a player is playing over his head according to their reports, he can sell high. If a player is underperforming in another organization (like the examples of Arrieta and Hammel) then he can identify them and make a savvy upside move. This sort of advantage is not limited to McLeod. Other GM candidates will have this background as well and it is one that perhaps the Padres will target.