Front Office Dream Team

Today was the day that the both the Chicago Cubs and Boston Red Sox had in mind as the unofficial deadline to have an agreement in place regarding compensation for the Red Sox allowing Theo Epstein to join the Cubs’ organization. It now seems that no official announcement will be made today. Instead the Cubs and Red Sox will remain in their staring contest until one side blinks. While the Red Sox have come off of their initial demands of Matt Garza or Andrew Cashner, Red Sox team president Larry Lucchino is still insisting that top pitching prospect Trey McNutt be included in the compensation package. That is not going to happen. The Cubs view McNutt as untouchable, and it is more likely that pitching prospect Jay Jackson will be in the compensation package. While the Major League Baseball has put a restriction on teams making official transactions during the World Series, it is likely that commissioner Bud Selig would allow the Cubs and Red Sox to make an official announcement on a World Series off-day. The earliest that could happen would be this Friday.

Meanwhile, the Cubs–and secretly Theo Epstein–are reaching out to some of Epstein’s former Boston colleagues to see if there is interest forming the same front office that led the Red Sox to the World Series title in 2004. The expectation is that Epstein is not going to be allowed to bring any of his current Red Sox assistants with him to the Cubs, so the Cubs are beginning to reach out to executives that were once with Epstein in Boston but have since moved on.

Once news broke of Epstein agreeing to a 5 year, $20 million deal with the Cubs, reports surfaced shortly thereafter that Padres’ Vice President of Baseball Operations Josh Byrnes would follow Epstein to Chicago. As it turns out, Byrnes may be a fall-back option for Epstein and the Cubs. Jon Heyman of Sports Illustrated is reporting that the Cubs are eyeing current San Diego Padres’ General Manager Jed Hoyer to join Epstein in Chicago. Heyman mentions that Byrnes could still be the one to land in Chicago, it just seems like the Cubs and Epstein prefer Hoyer. In addition to Hoyer and Byrnes, Epstein may have his eye on Padres’ Assistant General Manager Jason McLeod. Hoyer, Byrnes , and McLeod all worked under Epstein in Boston before they moved from the organization to advance their careers.

This is where things get interesting. If Hoyer does come to Chicago, it will not be as an assistant. Instead, Hoyer would likely be named General Manager with Epstein operating under the President of Baseball Operations title. The chances are increasingly likely that Epstein will likely only have the President of Baseball Operations title, and he in turn, will hand pick the next General Manager of the Cubs. It would seem that the preferred option for Epstein and the Cubs’ front office is for Epstein to be President and Hoyer to be General Manager. Such a scenario is also possible for Byrnes, who could also serve as the Cubs’ general manager with Epstein being the President of Baseball Operations. No matter what scenario plays out, Epstein will still be the end all, be all in the Cubs’ front office.

If Epstein and the Cubs are able to lure away Hoyer or Byrnes from the Padres’organization, it may be the biggest coup in the history of the Major League Baseball. Such a pairing would automatically put the Cubs’ front office among the best in all of baseball. The underlying benefit of the Cubs’ going after Hoyer or Byrnes to be their general manager–with Epstein’s approval of course–is that seemingly help their compensation negotiations with the Red Sox. Many feel the Red Sox have the leverage in negotiations because they already have Ben Cherington in place as their General Manager, while the Cubs have no one in place as their General Manager. Thus, if Hoyer or Byrnes were in place as General Manager, the Cubs would be in a position to walk away from negotiations with the Red Sox if need be.

While the Padres resorted back to the bottom of the National League West division this season with 71 wins, the team is a year removed from a 90 win season. Then once you consider the impact of losing Adrian Gonzalez this past winter, the Padres fall seems more justified. Regardless, under the leadership of Hoyer and Byrnes the Padres have seen an improvement in their farm system that will likely pay off on the Major League roster within the next few seasons. That same leadership is what the Cubs should expect, if either is put in place as General Manager with Epstein being front-man.