Photo credit: Kelly O'Connor

Photo credit: Kelly O’Connor

Right now, the Boston Red Sox appear to be in holding pattern until free agent southpaw Jon Lester makes his final decision. While Boston’s reported offer of 6 years, $130M is a strong submission, the Chicago Cubs are currently the highest bidders while the San Fransisco Giants are also in contention. Boston and Chicago’s offers are reportedly separated by just $8M dollars, which seems like a lot to us common folk, but there isn’t a whole lot that you can do with $138M, that you can’t do with $130M. Lester himself even said that he’s not looking to go to the highest bidder, and that family comfort will play an large role in where he signs. Lester’s familiarity with the Red Sox organization, the fans and media, and the city itself makes Boston a strong candidate to bring back the starter. On top of offering a familiar environment and personnel, Boston offers an opportunity to compete right away; which is something only the Giants can also say. In signing with the Cubs, Lester would be investing Theo Epstein and Jed Hoyer’s vision of a prospect driven roster, which is still two or three years away from coming together.

  • Should the Red Sox lose out on Jon Lester, Oakland Athletics’ left-hander Jeff Samardzija appears to be one of Boston’s top trade targets. In recent trade speculation, Boston’s short stop prospect Deven Marrero seems like a player that would intrigue Oakland, given that the A’s traded Addison Russell this past summer. But Marrero alone won’t be enough to reel in a pitcher of Samardzija’s caliber. Boston will need to delve deeper into their hoard of prospects in order to come up with a more enticing package. (Is Deven Marrero the key to a Jeff Samardzija trade?)
  • Right now Jon Lester is one of the best starters in the game, and can be had for just money. While Boston already has a final offer of 6 years, $130M on the table, the team could justifiably offer the lefty $150M. The Red Sox have the money and payroll flexibility to allocate $25M a year to Lester and not have to feel bad about it. While the later years of a 6 year, $150M pact might not see the same production as the first few, the opportunity to sign an elite player for immediate success is a luxury Boston can take advantage of. (Is Jon Lester worth $150 million to the Red Sox?)
  • Tweet of the day: This tweet wins the offseason in a landslide victory