Found a great article about how the Cubs' GM, Theo Epstein, is going to approach this offseason:

http://espn.go.com/blog/chicago/cubs/post/_/id/27875/epstein-were-good-enough-to-compete

 

The Cubs will be pursuing outside talent and free agents, but won't be desparate about it.

 

“I know we’ll get a bunch of columns saying we missed our guy,” Epstein said. “I’m not ashamed of that. To be a world-class organization you can’t be afraid of perception. You have to put yourself out there and look stupid at times.”

 

Is Epstein preparing fans for a letdown when free agency begins? Perhaps. But he’s also being realistic. A team whose window is closing -- say the Yankees or even the Red Sox -- will be more willing to overpay for a free agent. The Cubs’ window is just opening, so that impact player might not arrive as soon as everyone wants.

 

Does this sound like an approach the Twins should be using?  How close is it to the approach the Twins are taking?

 

I'd answer "yes" and "close", respectively.  The Twins and Cubs are at similar spots in their rebuild.  Both have been able to establish some young players.  Both have highly regarded farms expected to produce impact talent.  Both have a shortage of good starting pitching.  The Cubs will presumably have more financial resources in the end, but timing that leap for an impact player is crucial in both cases.

Cubs have a TON of young hitters already up, and some very close. I think they SHOULD be buying pitching, because they have none close. I think they are wrong, very wrong, about this.

Could we replace "Cubs" with "Twins" and call your statement equal?

The Cubs definitely positioned themselves to add some starting pitching when they shipped out Samardzjia and Hammel - They could be looking to add arms via free agency, but they probably have as good a shot as any at adding some via trade. They still have Edwin Jackson on the books - I think at this point the Cubs would consider it a success if another team takes his contract off their hands. Not so much because they need the money, but it could be better allocated elsewhere.

IMO the Cubs seem to operate a lot like the Twins.  They draft BPA even when fans scream to draft a pitcher.  They make solid trades and have been fortunate enough recently to have players that teams really wanted and were willing to over pay for.  Their best pitching crop is in A ball right now pretty much like the Twins.  

 

The main difference is the Cubs were more aggressive in the international market a year ago and when push comes to shove I think they will extend or re-sign more of their players than the Twins will as they will pay for talent when they need it.

 

I too think the Cubs have the pieces to trade to get what they need so they don't necessarily need to spend big to get good pitching.  They have a lot of guys who in the future should hit for power and possibly average on that team. They could be a very scary offensive team in a few years.  The pitching they need won't be far behind.