The Chicago Cubs have been absolutely pathetic to watch this year, but do have some very good young pieces to build a team around. I believe that their big market status will allow them to spend some money AND build the organization from the ground up through the draft at the same time. I don't believe Tom Ricketts brought in Theo Epstein to just sit on his hands for 3 years hoping prospects pan out, and that's why I think the Cubs will be very active this winter on the trade and free agent markets. These are the 5 players that I think the Cubs should make a run at.
I am not a fan of Dale Svuem. I believe he's handled the young kids wrong, and his moves have been questionable at best. I don't think he was given a chance to succeed, but at the same time- you can't treat your young players the way he has to a certain extent. Terry Francona is one of the best field managers in the last 25 years, and it's a shame Boston ran him off like they did. I'd love to see him in Cubby Blue because I think he would be perfect at handling veterans and youngsters alike.
Who Knows if Pedroia is available, but after sending half their team to the Dodgers- I believe everyone is available for the right price. If he is available, the Cubs should strike for him and the number 3 man on this list. Pedroia would be inserted into a lineup that has Anthony Rizzo, Starlin Castro, and Alfonso Soriano and that would give them a solid core offense. He's still a good defender and a dirt dog kind of player and that energy would rub off on the clubhouse. A trade for Pedroia would immediately give this team life.
Jon Lester is coming off a down year, and with the transition going on in Boston, no one knows who will or won't be made available. He will have to come over via trade, but if he's on the market- Theo Epstein is a big fan of his. I think in the right situation, Lester would thrive once again. I think the AL has figured him out, and a move to the NL will benefit his career. If the Cubs can get him without tapping into Javier Baez, Albert Almora, and Jorge Soler- you have to make it happen. The Cubs don't have the pitchers coming up through the system so a quality rotation will have to be bought at this point in time.
Josh Hamilton is a monster. Every team would want him for the right price and the Cubs are no different. If the Cubs added Hamilton to a lineup that had Starlin Castro, Dustin Pedroia, Alfonso Soriano, and Anthony Rizzo in it- holy cow. All of a sudden the Cubs are a different team. The question will be how many years can a team get Hamilton for. I would imagine the Rangers are still his number 1, but I'm not sure they get something done there. The Yankees, Red Sox, Angels, And Dodgers would have a hard time bringing him to the fold, which could allow the Cubs to sneak in and make a huge sign. We'll see what happens, but he's very high on my wish list.
Zack Greinke is a must have. The Cubs don't have any young quality power pitchers coming up through the system right now, and if they want a rotation of power- they have to buy it. Greinke is the best arm on the market this winter and will be high in demand. I believe you can give him the ball every 5th day and you have a chance to win and the Cubs haven't had that since 2003. If the Cubs spend some money, Greinke makes the most sense. Greinke, Lester, Garza, Samardzija is all of a sudden a rotation to be dealt with.