Theo Epstein to Cubs: How Long Will It Take to Have Chicago Competitive Again?

When the Chicago Cubs introduce Theo Epstein as their new President Tuesday, many will be wondering one thing...

When will you bring us a World Series?

Sure, that is the ultimate goal, but let us not forget that the Chicago Cubs went 71-91 in 2011 and were actually worse than the Pittsburgh Pirates for the first time in a very long time.

On a positive note, the Cubs did have a better record than the Houston Astros, but then again who didn't? Exactly, everyone did.

Epstein and his likely appointed general manager Jim Hoyer are going to do whatever they can to bring the North Slide some satisfaction, and expect that to start out sooner then many think.

Here is an outlook on the Theo Epstein era in Chicago over the next four years.

Key Acquisition: Prince Fielder, First Base

Central Division: Second

Playoffs: Missed

Why

The Chicago Cubs will miss the 2012 playoffs because they will just be getting a feel of things. If the St. Louis Cardinals keep Albert Pujols around, it is hard to believe that the Chicago Cubs will be able to make the jump over them.

However, with Prince Fielder traveling South from Milwaukee, that, and a few other transactions, will be enough to at least put the Cubs over the Brewers and Pirates.

Key Acquisition: Matt Kemp, Outfield

Central Division: First

Playoffs: NLCS

Why

Many of you are saying "ya right!", but this isn't such a long shot. If the Chicago Cubs do get Prince Fielder in 2012, and then bring in Matt Kemp in 2013, the Cubs will be one of the most dangerous teams.

That would be some firepower, especially as Starlin Castro will be starting to get into a consistent groove as well.

The pitching woes will still need to be answered coming into 2013, but that is one of Theo Epstein's biggest challenges. Don't expect him to fill the rotation with big names head to toe like the Phillies, Yankees and Red Sox, but rather with consistent pitchers who can perform.

Key Acquisition: Roy Halladay, Starting Pitcher

Central Division: First

Playoffs: World Series Champions

Why

Yep, it will take about three years, but in 2014 the Chicago Cubs will finally be hoisting that World Series trophy.

Theo Epstein will continue to build this club through the farm and free agency/trades, but the move that will put them over the top will be the acquisition of pitcher Roy Halladay.

After the 2013 season, the Phillies and Halladay have an option for the 2014 season. At $20 million, I don't see the Phillies keeping Halladay around, because he will likely no longer be the threat ace he was. With the Chicago Cubs starting to make strides, Epstein will get Halladay to fill out the rotation, as he will fill the number two or three spot.

After saying for many years this year will be the year, it finally will be.

Key Acquisition: Re-Signing Starlin Castro

Central Division: First

Playoffs: NLCS

Why

Alright now, let us not get too greedy. The Chicago Cubs are going to win one World Series over the next four years, but it is quite a feat to win it twice—especially in a row.

While Epstein will extend Starlin Castro either in 2012 or 2013, the Cubs All-Star shortstop will likely be looking for big money after the Cubs claim their first World Series championship.

Castro is going to be just as big as players like Derek Jeter, and he will be demanding a lot of money. Expect the Cubs to focus most of their 2015 funds on their young stud shortstop in order to keep the Cubs relevant for many years to come.

Terry Francona, Manager: Theo Epstein is going to bring Francona back, and the two are going to make history in ending the Chicago Cubs' ongoing curse. They already have the Red Sox on their resume, so expect these two to make magic happen.

Ryne Sandberg, Bench Coach: Ryne Sandberg will be in Chicago in 2012. He wants to get his career started, and there is no better way than guaranteeing himself a future spot then grabbing a role on the bench. Francona will groom Sandberg to become the next great manager.

Greg Maddux, Pitching Coach: While Maddux is contemplating a family or work for 2012, Theo Epstein will ultimately convince the Cubs legend to stay in Chicago for a few more years and help him improve this club. There is no one who could be a better role model to these young pitchers than Maddux himself.

Kerry Wood, Bullpen Coach/Pitching Coach: Kerry Wood is likely going to retire after the 2011 season, and I wouldn't be shocked if Epstein kept him around for awhile. Wood is the face of the Chicago Cubs, whether he is playing or not, and it would be a shame to see him elsewhere again.

Expect Wood to find himself a role with the organization, likely as a bullpen coach. Once Maddux decides to finally walk away from baseball, Wood will step in and be the pitching coach for the Cubs.