Contractually Speaking: The Chicago Cubs' Payroll

Since it's mid-November and there are rumors flying about who might be traded, who's available, who isn't, and why a team should or shouldn't trade someone, perhaps a moment of focus on how long players are signed for can lend some perspective to help us answer these questions.

In the case of the Chicago Cubs, there are lots of reasons to be happy coming off 2008. They had the best record in the National League, the Rookie of the Year in Geovany Soto, perhaps the biggest surprise in the N.L. in 17-game winner Ryan Dempster, and a regular season that could be rated, as a whole, as superb.

Then October arrived. The Cubs did not.

And so here we are, in November (again), trying fix something that might not necessarily be broken. What are the pieces Cubs General Manager Jim Hendry has in place to make some moves, and what decisions does he need to make to try to make Year 101 special in Wrigleyville?

There are a number of players that are free agents and could potentially leave the team. Dempster, closer Kerry Wood, backup catcher Henry Blanco, outfielders Jim Edmonds and Daryle Ward, and reliever Bob Howry are all available on the market.

Edmonds might retire, while Ward and Howry find themselves to be replaceable at less cost. The three free agents of consequence for the Cubs are Dempster, Wood and Blanco.

Dempster is said to be looking for a multi-year contract, and there have been reports the Cubs may offer him a four year deal. Meanwhile, Wood turned down more money and more years from other cities to stay in Chicago. He has consistently maintained his preference to stay with the Cubs, and having finished fourth in the N.L. in saves last year should earn him a call back from the North Side.

Blanco could stay or could go; he was a valuable asset off the bench for a number of years, but youngster Koyie Hill appears to be ready to move up to the majors.

There are a handful of Cubs that are arbitration eligible this winter. Outfielder Reed Johnson, relievers Neal Cotts, Chad Gaudin, and Michael Wuertz, and infielder Ronny Cedeno. Wuertz had some issues last year and subsequently spent a few months in Iowa.

However, the other four on this list could all see a nice pay raise. Cedeno's name has been floated as trade bait, as he finds himself stuck in a quagmire for playing time in a crowded Cubs infield behind Ryan Theriot, Mark DeRosa, and Mike Fontenot. Cotts will likely get a look this coming season as the matchup lefty in the bullpen, with Scott Eyre having been traded to Philadelphia last year (how'd that work out for him?).

Expiring contracts are a dangerous, double-edged sword in baseball. While they grant a general manager the hope of flexibility both in trades and future free agent hunting, they also could define the amount of time a specific group is together. Players with one year left on their contract give GMs a lot to think about and work with—and not always in a good way.

For the Cubs, there are three players of consequence that have just one season remaining on their current contracts: Rich Harden, Jason Marquis, and DeRosa. Hendry intimated when he traded for Gaudin and Harden that he would like to have both of them, especially Harden, around for a while.

The Cubs picked up Harden's option for 2009 at $7 million and will likely negotiate a longer-term deal if the starter can stay healthy. Marquis, in my eyes, brings the value of eating up 200+ innings every year. How good those innings are is to be determined, but his arm is strong enough to throw whenever needed.

DeRosa is a wild card, though. Many pundits pegged him as being overpaid when Hendry signed him in November of 2006. But at $4.75 million in 2007, I challenge you to find another player with the versatility and experience "DeRo" brings to the table that performed as well for such a salary.

His contract escalates to $5.5 million for 2009, which, for a player who drove in over 80 runs and hit over 20 home runs, is highway robbery.

What to do with DeRosa is a big question for Hendry, however. Fontenot is younger and bats left-handed, something the Cubs sorely need in their batting order. He also doesn't make anywhere near $5 million because of his tenure in the majors.

He showed in 2008 that he swings a big bat and plays solid defense next to his college teammate Theriot. This could make DeRosa trade bait this winter, with his production-for-cost value as high as it probably ever will be and his expiring contract making him doubly enticing to teams in a cost-cutting mindset.

Perhaps the most intriguing winter in Chicago will be after the conclusion of the 2010 season. In two short years, the contracts of 17-game winner Ted Lilly and first baseman Derrek Lee expire, with Hank Aaron Award winning third baseman Aramis Ramirez holding a player option for 2011.

In their current form, Ramirez and Lee are the heart of the Cubs' batting order. While Lee's production has declined in each of the past two seasons, Ramirez has been the first consistent third baseman the Cubs have had since Ron Santo in the 1960s and '70s.

Of the Cubs' veteran core, there are only three players who's contracts extend into 2011: Carlos Zambrano, Alfonso Soriano, and Kosuke Fukudome. These three are due a combined $64 million in 2011, after which Fukudome is a free agent.

Other than these contracts, the Cubs are relying on their farm system to buoy their veterans into contention. This presents another issue for Hendry; all of these "kids" that are playing well will also need to get paid at some point. How much will Soto, Theriot, and Carlos Marmol be worth when their rookie contracts run out?

What about young starters Rich Hill and Sean Marshall? If they step into the rotation and perform well, how much could they stand to earn in the future? And even though the Cubs gave Jeff Samardzija a lot of money to quit playing football at Notre Dame, if he develops the potential we saw in 2008, what could he be worth in three more years?

As the cliche goes, the Cubs' window could be closing. They have an aging batting order, the bulk of which has two years or less remaining on their contracts. This would lead even the most casual observer to say, "The Cubs need to play for today and worry about tomorrow when we get there. We won't have Lilly, Lee, DeRosa or possibly Ramirez in three years, so if we're going to do something it has to be in 2009 or 2010."

Which is what brings me to my next issue.

One player who intrigues me on the Cubs' horizon is young outfielder Felix Pie. In light of all the contractual situations, he presents one of the toughest dilemmas for Hendry. He has run out of minor-league options, meaning he is either on the Cubs every day 25-man roster for the entire 2009 season or he's a free agent.

How does a general manager, if Hendry indeed has a similar mindset to the one referenced in the previous paragraph, justify giving a full-time roster spot to a player that has 72 career strikeouts and 58 career hits?

Pie has taken on the mantel of "Golden Boy" among Cubs faithful. Is he Jerome Walton? Roosevelt Brown? Brant Brown? Or is he the Kenny Lofton we've been told he could eventually become? And, more importantly, where does he fit on a team trying to win now?

The biggest argument in Pie's favor is, given the opportunity, he could figure it out in the majors. But with Johnson, Fukudome, and Soriano already signed to play in the outfield, and the pressure to win growing, how does Pie earn his playing time if he continues to struggle?

And with a left-handed bat for the middle of the batting order becoming an annual issue, the most likely place to find that player would be in the outfield. How does that impact the future of Pie?

Hendry has a lot of issues to deal with, and has a lot of pieces to work with. While there is an understandable questioning of how Cubs' fans can be so selective and picky after the success of last season, the reality is that the team came up short again.

Finding the right, winning formula has eluded the franchise for a full century now, and the amateur general managers we all consider ourselves can't help but offer our best solutions to this 100-year problem.