As the Cubs season trickles to a close I find myself wondering what the future has in store….or doesn’t.

Five questions …….five lingering little thoughts of doubt, and intrigue that keep me up at night and threaten to strip me of my sanity (not really, but it sounds more dramatic this way).

Without further ado, here they are…….

Question 1: How many moves need to be made?

Recently Jim Hendry made the statement that the Cubs are “four for five moves away from contending next year”.   This concerns me because over the past five years you will remember that Jim has made statements along the lines of “We really only need to make a move or two to contend” ….now that number is up to four or five.

My theory is that if Jim thinks we need to make one or two moves then we really need to make four or five.  If he thinks we need to make four or five then we need to make eight or nine and so on.

His favorite line going into each season is “If  (insert player name here) plays like they did in (insert said players best year in the last five here) then we should be just fine.”

Hope floats, huh Jim? Not quite, and the Cubs have paid for that two straight seasons.  I can remember earlier on in the decade when we were “hoping” for Prior and Wood to “return to form” and nowadays it’s A-Ram, Soriano, Soto, or Zambrano. Hope doesn’t float on the Northside and should not be used as a strategy to win.

Question #2: What if Mike Quade pulls off the sensational?

Lets just say Mike Quade wins 80% (or some ridiculous number) of the games down the stretch.  I know, he has won his first two, and no I am not drinking anything.  Just wondering what kind of wrench this throws into the management search?

Most of Cub nation wants to see either Ryne Sandberg or Joe Girardi as the new Cub Manager.  What if though? What if Quade rolls through the end of our season? What if he goes a miraculous 30-7 down the stretch?  How do you look at the guy and say thanks for effort, but third base is your home.

Then again, how do you pick Mike Quade over Ryne Sandberg or Joe Girardi? That’s like picking a Yugo instead of a Porsche or Mercedes….or is it?

Question #3:  Who will be the Cubs first baseman next season?

Okay, finding a guy who can pick it like D-Lee will be a challenge but with all the defensive holes on this team we can ill afford another liability in the field.

I am also a little afraid we are going to grab a guy on the downside of his career.  One name that stands out, and is the one I fear the most becoming a Cub, is Adam Dunn.

Yes Adam hits for power, but he also has suspect defense (that’s being kind) and he strikes out a ton!  We have a lot of this already, the only problem is I am not sure what else will become available?  Do we resign D-Lee?

This is a scary topic and really needs your thoughts, what do you think the Cubs best options are?

Question #4: What new and obnoxious  advertisements will we see at Wrigley next year?

I walk by the Kraft noodle at least once a week.  Every time I walk by I feel like the Cubs organization is collectively standing on the corner of Clark and Addison hookin’!

“What can I get for $10?”

“Anything you want!”

What new and obnoxious, soul sucking, yet revenue generating ideas will flow from the Cubs brass for 2011?

Question #5:  What is the most important move that needs to be made?

Of the four or five moves needed per Jim, what do you think is the greatest need for this team?

Do we need a true ace on the mound? A stopper? A Cliff Lee type guy?

How about that power hitting first baseman with a good glove?

I would say the relief core needs a boost but picking up relievers in free agency is a large expense and usually a gamble.  It seems to me that relief pitching is very much luck of the draw.  You either happen to stumble upon it within the organization and it flashes for a season or two and dies out, or you try to buy it and almost always end up disappointed.

Among the many needs this team seems to have,  is this where they want to sink their money? Or is there a greater need?

So there you have it!  Five questions, among the many, for you to answer. What are your thoughts?

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Chet West is an IT professional living in Minneapolis, MN with his wife and two daughters. He has a pug named Banks and loves photography. Follow him on Twitter @chetwest19