1.) Which big pitcher will the Cubs sign?
David Price is the obvious choice, and the Cubs should be viewed as the favorite to land Price up until the moment he signs with someone else. The Maddon-Price connection, as well as the opportunity to pitch in a rotation with Jake Arrieta and Jon Lester, will be a big attraction for Price. He won’t have the hopes of an entire franchise shoved on his shoulders with those two to back him up. The Cubs will also make an offer to Zach Greinke, but if Greinke does not re-sign with the Los Angeles Dodgers, the only other logical landing spot for him is up the coast in San Francisco. Johnny Cueto is probably a no-go for the Cubs. If the Cubs are getting really aggressive this winter, they could also pursue Jordan Zimmermann. That’s probably too much money for even the Cubs.
The Cubs need an upgrade to the back-end of their rotation, and they have the money to spend for it. It’s only a matter of whether the team makes one or two big purchase at starting pitcher. The most likely scenario has the Cubs signing Price, and trading for a fringe ace like Tyson Ross.