No, they already have Ellsbury and Drew in the outfield and Big Papi at DH so they only need one of those guys and not both. Hopefully they'll just re-sign Bay.
The Red Sox are a better organization that to sign both. They only need one. I would assume they stress trying to sign Bay because he did a very fine job during the past season.
Probably not. They wouldn't have room for both of them in the outfield unless they trade Drew or Ellsbury. That's not very likely, as is getting rid of Ortiz and having Bay DH. They'll probably just sign one of them.
NO...they both will not stay...if u ask me, holliday is going to the sox and jason bay is going to seattle to stay near his family
maybe he might even go to l.a
I think the Sox will resign Bay, but getting Matt Holliday would be tough. The Cardinals, Mets, Yankees, and many other teams are looking to land him so if the Sox can blow past the competition, they will get Holliday.