Offseason Outlook: Chicago Cubs

The Cubs are at a crossroads this offseason, as they seek a new GM and face the temptation of adding more big free agent contracts.

Guaranteed Contracts

Contract Options

Arbitration Eligible Players (estimated salaries)

Free Agents

The Cubs were a $134MM disaster in 2011.  Despite all their spending the team hasn't reached the playoffs since '08.  This summer they fired longtime GM Jim Hendry, whose teams made the playoffs in three of nine seasons.  Owner Tom Ricketts seeks a more analytically-inclined GM to craft the roster.  His other criteria include a commitment to player development and a track record of success.  Ricketts has pledged silence during the ongoing search, but reports suggest he's initially targeting current GMs such as Theo Epstein and Andrew Friedman.  The job security of Mike Quade is in question as well, as a new GM may want to hire a new manager.

The new GM will have to spend free agent dollars wisely, which was often a problem for Hendry in recent years.  A steady payroll for 2012 could give the Cubs a hefty $40MM to work with in 2012 salaries.  The possibility of a quick turnaround tempts Ricketts, who referenced the Diamondbacks' success in a recent interview.  The D'Backs were fairly restrained in free agency last winter, but the Cubs are in a position to throw around some cash in the coming months.  The potential areas to upgrade are plentiful, with openings at the infield corners, right field, the rotation, and in the bullpen.

The Cubs may have to make a concession at third base.  The opportunity to re-sign Ramirez — easily the best free agent third baseman available — to a below-market contract hasn't motivated them, and the team's offense will suffer without him.  The first base market is appealing, with superstars Albert Pujols and Prince Fielder options to take up more than half of the Cubs' payroll flexibility.  With such a clear rotation need, though, the Cubs could lower their sights at first base and re-sign Pena or pursue Michael Cuddyer.  Cuddyer's versatility could be a nice match for the Cubs, who have openings at all his positions.

The Cubs appear intent on unloading Zambrano, whose performance is probably worth a few million dollars to some team.  Chone Figgins could be a reasonable target given the Cubs' third base vacancy and the limited options at that position, though the Mariners would have to be willing to take another potential head case from the Cubs.  Assuming Dempster returns, he'll join Garza and Wells in the rotation.  If a quick fix is the goal the Cubs would be best-served by shopping in the high-end section of the market: C.C. Sabathia, C.J. Wilson, or Yu Darvish.  On the other hand, signing any of the potential $100MM+ players this offseason would hardly break the Cubs' cycle of piling on burdensome contracts.

I can't picture the Cubs slashing payroll given their attendance and rabid fanbase, but I'm also not convinced they're going to come away with Pujols, Fielder, Sabathia, Wilson, or Darvish.  With so many needs, the Cubs could easily spread their surplus among four or five veterans.  Other big-market teams have shown an ability to contend and improve the farm system simultaneously, a strategy the Cubs appeared to finally initiate with a slew of over-slot signings in the June draft.

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