Now that the Yankees have won the World Series and the season is officially over, it’s time for Cubs fans to start thinking about what the team needs to do this off-season. Can the Cubs do anything internally to upgrade their bullpen? Can they afford to wait on their high-priced player to contribute or should they deal them to a team for prospects and re-build? We identify some needs, some players that need to go, and some free agents that Tom Ricketts need to sink some money into.

The Cubs have a lot of dead weight on their roster. They have used a lot of money to sign high-priced players that haven’t lived up to their potential. Alsonso Soriano, Milton Bradley, Kosuke Fukudome, and Carlos Zambrano didn’t have great seasons last year and their combined payroll is most than many small market teams. Their pitching staff, especially their closer position, was very rocky and Carlos Marmol completely imploded with a WHIP around 1.50 for most of the year.

Let’s start off with players that are free agents from the Cubs. Kevin Gregg, Reed Johnson, Rich Harden, and John Grabow all are free agents this off-season. First off, let Gregg walk, he wasn’t good on back-to-back days and he played himself out of the closer role. I would also agree with letting Harden leave as well, there are some nice 4th and 5th starters in this free agency pool that could step in and go more than five innings. Harden put extra burden on the bullpen to close games and many of the games Harden would give up a lot of runs the last inning of work. I would say to re-sign Grabow and Johnson to contracts. Grabow is a nice left-hander that could be a possible closer candidate. You would have to give him at least a three-year deal, but I would be okay with that, he showed promise with the Cubs. Reed Johnson would be a nice two-year player as a platoon with Fukudome in center. He is nice off the bench and pinch-hits very well.

Tom Ricketts needs to spend money to make this Cubs roster a contender. You have at least one more year of Pinella as your manager and you need to stack the deck. As a new owner, you will need to make a splash, so your first move should be to sign Mark DeRosa and get him back on the Cubs. The biggest mistake that they made was trading him away. They did get a few nice minor-league pitchers that will probably be on the 40-man roster this next season, but throw the check book at DeRosa. He probably wants at least a three or four year deal, but try and get him for $10 million a year. They shouldn’t care what it costs, it will bring all the Cubs fans together and support Ricketts as the new owner. DeRosa can play nearly every position and if there is an injury, like last year’s injury to Aramis Ramirez, it won’t cost the Cubs games with DeRosa filling in. If you go another season with Aaron Miles and Jeff Baker as your options in case of an injury, you’re going to be hurting.

The other free agents that you need to look at are Bobby Abreu (who they should have signed last year), Chone Figgins, Justin Duchscherer (could be a nice, cheap option as a 4th starter), Randy Wolf, Ben Sheets, and Miguel Tejada (if he would agree to a one-year deal). Abreu will be looking for a huge contract and will probably be out of the Cubs price range. Figgins would also be looking at a huge contract and it would be a multi-year deal, it could be risky, the older he gets, the more his speed could diminish. Justin Duchscherer was out all year recovering from surgery, but his 2008 season was amazing. I know he has injury concerns now, but they could get him at a discount. I would love if they signed him, his upside would be tremendous. Randy Wolf is dependable and you know what you get with him. His upside would be last season when he was coasting through games with an ERA around 3.00. He could have played himself get into nice contract, so the Cubs may have to outbid a few teams if they really want him. I listed Ben Sheets because I think he still has something left in the tank. Who would have thought that Sheets and Jake Peavy would be in baseball no-man’s land, if you add in Brandon Webb, those were the best three pitchers in the league just two seasons ago. You could get Sheets cheap, I would love this signing. Miguel Tejada is the last on my list and rumors have been floating around since he was in Baltimore of a possible deal/signing with the Cubs. If the Cubs were more of a contender, he would sign a one-year deal, but it doesn’t look like they are on the short-list to win the World Series next year, so it would be unlikely.

The Cubs need to do their best to move some player this off-season. Milton Bradley would be the best candidate for this to happen, mostly because of his attitude and the fact that they still owe him more than $20 million over the next two seasons. Some rumors are flying around a trade with the Blue Jays for Vernon Wells, but I don’t see how that makes sense. Wells is a nice player, not great, but he is signed to an ungodly contract. Wells still has five years left and $107 million dollars left on his deal, but the rumor is that the teams would split the contract in half. I still don’t see this happening for the Cubs, since they have received plenty of interest from other teams and the Blue Jays would have to sweeten the deal.

Jake Fox is another player that has to be moved before next season. If the Cubs were in the American League, Fox has the ability to be their franchise designated-hitter for many years, but unfortunately he doesn’t have a position on the Cubs. If they could move him for a nice young starter, it would be in the Cubs best interest to make that deal. The Orioles have a nice stash of young pitchers and we all know how the Cubs love to make trades with the Orioles. I can see this happening, even though I wrote many posts about how the Cubs need to stop trading with bad teams and getting little in return.

Tom Ricketts has a lot to think about this off-season. A lot has been written if the Ricketts family can afford to add to the payroll and it has been a mixed bag of responses. They want to put the profits back into the Cubs and improve the facilities, but before you do that, make one push to get this team to the elite level. They did a great thing by signing Rudy Jaramillo as their hitting coach, he did some great things for the Texas Rangers. These are the things that the new owner needs to do to improve the team. Build the team around fundamentals and get these high-priced players to get back to hitting and pitching and doing everything right. I don’t know what the window of is on this team to be good, but it’s closing. Zambrano could bite the head off of a pitching coach any day, you never know.