The 5 Biggest Decisions the Chicago Cubs Have to Make This Offseason

The winds of change are blowing on the north side of the Windy City as president Theo Epstein has changed his tune from urging patience on the part of Chicago Cubs season-ticket holders to letting fans know the team plans to compete for the NL Central title next season. He's changed his tune because the rebuild is almost complete and the Cubs should be ready to compete again. 

In such an important transition year, the Cubs' front office has several key decisions to make. Whether or not they make the right decisions could be the difference between another disappointing year of baseball at Wrigley Field and the team's first division crown in seven seasons. Here are the five biggest questions Epstein and general manager Jed Hoyer face this offseason.

5. How Much of Edwin Jackson's Salary to Eat

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It seems clear after another disappointing season with the Cubs that the team is ready to cut ties with pitcher Edwin Jackson. The only big mistake of the rebuild so far, Jackson's contract is not nearly justified. According to the Chicago Tribune's Mark Gonzales, even Epstein has acknowledged the mistake, so 2014 could mark the end to Jackson's run with the Cubs.

If that's the case, no trading partner is going to approach paying the $13 million annual salary that Jackson is owed over the next two seasons. That means the Cubs are going to have to pay a lot of his contract even if he isn't playing for the team.

It's clear the team would prefer to have a group of young guys battling for a spot in the rotation rather than have Jackson take up a spot again. So what's the right amount of his contract to eat? $8 million? $10 million? The answer to that question, in the minds of the Cubs' front office, is going to help determine how much free space it has to offer top dollar to marquee free agents this offseason.

4. Whether or Not to Keep Kris Bryant at Third Base

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Technically this decision could be made during or after spring training, but the Cubs really need to devise a plan for where all of their young players are going to be playing in the big leagues. As the top prospect in baseball, Bryant's bat is going to be in the lineup sooner rather than later, but what position he plays still isn't set in stone. 

On the Kap & Haugh Show (h/t Chicago Cubs Online) Hoyer said the Cubs want to keep Bryant at third base, but he's not a stellar fielder there, and moving him to a corner outfield spot could allow the team more flexibility when it comes to shuffling other infielders around. On top of that, he wouldn't have to devote as much time to fielding if he played a corner outfield spot. 

The implications of moving Bryant to the outfield could be moving Starlin Castro to third base to make room for shortstop Addison Russell when he's ready to get called up. Again, this decision doesn't need to be solidified in the offseason, but a plan should be in place by spring training.

3. Whether or Not to Sign a Veteran Catcher

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Indicated by a report from ESPN Chicago's Jesse Rogers, the team appears supportive of 2014 first-round draft pick Kyle Schwarber catching, so the Cubs' front office may no longer be convinced Welington Castillo has a long-term future with the team. He has shown an ability to hit for power at times, but he hasn't consistently shown the ability to stay healthy or hit for average. 

Even if they wanted to make Schwarber the catcher of the future, he likely wouldn't be ready for big league action until at least 2016. If the team truly believes it can compete in 2015, it may consider pursuing a veteran like Russell Martin to give it a spark and a veteran presence in the locker room.

2. How Much to Offer Jon Lester

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All signs point to Jon Lester being the team's top free-agent target this offseason. He has ties to the Cubs' front office, the Cubs have money to spend and the team appears almost ready to compete. If the Cubs want to get Lester, they probably can.

However, that all hinges on the price tag he commands. As relayed by MLB.com's Carrie Muskat, Epstein has said that he will spend money this offseason, but only if it makes sense.

As a player, Lester makes a ton of sense. But just how much money will he command on the open market? He will easily command over $20 million annually, but will he command over $25 million a year?

How much the Cubs' front office is willing to bend on price could help determine if Lester becomes a Cub and how much money the team will have for remaining free agents.

1. How Much Money to Spend in Free Agency

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On top of just Lester, the Cubs need to plan how much they're going to spend this offseason. This year has a trio of great pitching free agents in Lester, James Shields and Max Scherzer, so the Cubs are sure to be active. Next season has some great pitching free agents as well, including David Price.

So do the Cubs spend big this season and go for the division in 2015, or do they spend a decent amount and go all in for 2016?

Nobody knows the answer to that other than Epstein and Hoyer, and even they may not know the answer to that at this point. How they decide to spend money this offseason could drastically change the course of the rebuild the front office has worked so hard on for the last three-plus seasons.