Organizational Rankings: #18 – Chicago Cubs

Organizations like the Cubs present some challenges in a series like this. They have some very obvious strengths – the printing press that is Wrigley Field, the ability to support a $140 million payroll, new ownership that at least appears to be committed to improving how the organization is run, and some really good players on the field. They also have some similarly obvious weaknesses – a lot of committed money to aging players, a front office with a long history of questionable decision making, and a roster that needs some good luck to contend in 2010.

If you just focus on the strengths, you can make a case for the Cubs to be a bit higher than this. After all, they have a real resource advantage over the rest of their division and some really good players in place. If a few things go right, they could steal a playoff berth this year, and they’ve got the finances to be a real player in the future. Their strengths are stronger than most teams strengths.

Likewise, however, you can just focus on the weaknesses and make a case that they should be lower. Their core is getting long in the tooth, with most of their best players being past their prime. They have some good young talent, but not a roster full of it, and the big contracts will hamper their ability to rebuild around guys like Soto and Castro. And, even with a sizable payroll, you can’t expect Hendry to spend it all that well, based on his track record.

When I try to balance the strengths and weaknesses, this is where the Cubs end up – in the middle of the pack, getting less out of what they have than most clubs, but having enough to keep them from being too bad. If the Ricketts demand that the front office catches up to the rest of the league, the team could rise pretty quickly – a more efficient front office could do wonders for the Cubs. There’s enough talent and enough money in Chicago that they should be a top ten franchise without too many problems. They aren’t there now, however. They may get there, but based on where they currently stand, middle of the pack is about as high as I can place them.