Crank that offseason plan: Chicago Cubs

I started with the Chicago White Sox and now I move onto the Chicago Cubs and what they should do over the course of the offseason.

MUST-MAKE DECISIONS

1) Milton Bradley: To trade or not to trade?

Without question you got to trade crazy Uncle Milton right? Perhaps not. With his former hitting coach Rudy Jaramillo on board the Cubs may have a shot at fixing their confused and disoriented right fielder. Of course, the Cubs want to trade Bradley ASAP but they may have to try to restore a little bit of value because he doesn't fit on many teams due to his antics and inability to provide adequate defense. He did, however, stay healthy which should help his value out a bit. A straight salary dump doesn't make sense and I don't think the club has a viable option in right field to repalce him, either.

2) John Grabow: long term deal, arbitration, or not?

I think this should be the easiest decision the Cubs make all offseason. Of course they, at the very least, offer Grabow arbitration but if he declines you can't let him walk, even for his type-A compensation. The Cubs haven't had an even remotely capable lefty out of the pen since "Stevie" was on the team and it's always difficult to find a reliable lefty on the open market. My best idea would be to offer him arbitration only if a long term deal cannot be reached.

FLEXIBLE DECISIONS

3) Who's on second? Jeff Baker, Mike Fontenot, Aaron Miles or somebody entirely different?

This has been a huge area of concern for the Cubs with no in-house candidate capable of truly holding down the job. I thought the Miles signing last year was weird from the get-go but I didn't expect him to be as bad as he was either. At this point I think you can rule out the Fontenot era and Jeff Baker isn't anything more than an better version of Andres Blanco so it would seem the best solution is to go outside the organization for some help be it by trade or free agency.

4)Do you make room for Jake Fox on this team somehow or do you look to trade him?

Fox was one of the better stories of the 2009 season for the Cubs but he's best served as a designated hitter for an AL team. He could have some value as a first baseman as well but neither position is open for him on the current club. He could be a valuable trade chip along with Josh Vitters to get a second baseman or a closer (both are areas of concern).

FREE AGENCY

5) Which positions are in most dire need of an upgrade?

Without a doubt, second base and closer are in the most dire need of an upgrade with the potential that right field an area in need of an upgrade as well. The rotation appears to be in OK shape.

6) Name three (or more) free agents you’d consider, at a price.

Sign Chone Figgins for 3-years at $12 million-per-year. The Cubs are going to be in a bidding war with just about every team with money to spend for the versatile and speedy Angel. Beauty of it is Figgy can play positions where the Cubs need the most help (OF and 2B).

Sign Billy Wagner for one-year at whatever price it takes to be the highest bidder.

Sign Orlando Hudson for 2-years at $8 million-per-year. He brings good defense and switch hitting skills which helps the Cubs two-fold.

TRADES

7) Name three (or more) realistic trades that could improve the Cubs.

Trading a package of Jake Fox, Josh Vitters and Jeff Samardzija to the Washington Nationals for Adam Dunn, Christian Guzman and John Lannan.

Is this too much to give up Cubs fans? It would fix the Cubs need for lefty power by adding Dunn and fill the hole at second base with Guzman. Lannan has a career ERA under four and just posted 3.88 ERA in 2009. Fox doesn't have a position and as long as Aramis Ramirez stays healthy there's no room for Vitters either. The Nationals would be up for this deal because Dunn doesn't help them win in the future and Guzman is overpaid.

Option Two: Trading said package for Brian Roberts. It wouldn't be a Cubs offseason story without an attempt to trade for Roberts.

SUMMARY

Basically, the plan is laid out. The Cubs need to upgrade second base and find a closer. It's more important then trading Milton Bradley, trust me. The good news is that there are plenty of options from both a free agency and trading standpoint for both positions. It should be a relatively easy fix. I'm not too sure about the back end of the rotation but there's more important issues to address. The other key for the 2010 season? HEALTH. The Cubs should be neck and neck with the St. Louis Cardinals if everyone stays healthy. Aramis Ramirez wasn't 100 percent at any point this season and when you're missing one of your top-two hitters, it's bad news. The Cubs also never had a closer this past season, either. Kevin "Kelly" Gregg was a joke from the get-go and general half-ass playing did this team in (see Phonsi and Geo Soto). Bounce back seasons all around and the Cubs are contenders again with just minor tinkering needed. Here's looking at you Rudy J.