I will be the first one to applaud Hendry for trying his best to reconstruct the shambles of a team called the 2006 Chicago Cubs. However, unless some players reverse their recent trends, any serious consideration for a trip to the world series is doubtful.
One of the bigger obstacles the team has to overcome is their propensity to issue walks.
We all know that the free pass is exactly that, a gift to your opposition's offense. If the best teams only hit safely at around a 280 clip, the present makeup of the Cubs rotation looks to increase their opponents OBP considerably.
If the Cubs rotation was backed by a superior defense, they would be able to overcome some of the damage done via the walks issued. This unfortunately is not the case as the team sets up presently.
It is highly unlikely that many changes will take place in the rotation, however the Cubs do have one wild card that could effect the rotation significantly. That is Mark Prior. Prior's re-emergence to his form of old will help immensely in the glut of walks issued as well as increase the strikeout total. The increased strikeouts alone can help relieve much of the pressure on the suspect defense. Let's face it, the more outs that can be attributed to a strikeout, the less outs you need to rely on your defense for.
As far as upgrading the defense goes, there are still some moves that are possible. A decision has to be made by Pinella if he believes that the increased strength of the outfield defense by bringing up Pie, can more than make up for the loss of run production by putting Jones on the bench or trading him outright.
The team defense is already suspect up the middle with Barrett. Although DeRosa seems to have decent ability he doesn't have much more playing time at 2B than The Riot has.
All in all, the way the rotation projects out and the assemblage of the proposed lineup, it is questionable at best if the Cubs will be able to out slug their opposition enough to be taken seriously as a strong candidate for the post season.