It is the biggest decision this organization has ever been faced with. Careers may be defined by it. Fans may be won or lost because of it.

What are the Arizona Diamondbacks going to do about Brandon Webb?

They have until five days after the completion of the World Series. Either they pick up the $8.5 million dollar option on his contract or they buy him out for $2 million and he's a free agent. And the former Cy Young award winner has made it pretty clear there will be no restructuring of the contract to account for the mystery of his shoulder.

There is only one other moment in time that comes even close to the crossroads this organization now sits at: the decision to trade Curt Schilling to the Boston Red Sox in what ultimately was a three team trade that brought Richie Sexson to Arizona. In breaking up their dynamic duo the D-backs were betting the house that the increased offense would offset the loss their World Series Co-MVP. Schilling won a title in Boston, Sexson played 23 games and the D-backs lost 111 games, costing both Bob Brenly and Jerry Colangelo their jobs.

Oops.

And yet this decision looms larger than that one in my mind.

Reason #1: The Great Unknown. If Brandon Webb is going to be "Brandon Webb-Best Pitcher in the National League" of course you pick up the option. Do you know for sure he will be? It's a shoulder injury and they are tricky, tricky things. And the timing absolutely stinks from the D-backs perspective; they're not going to know anything more about the shoulder when they have to make this decision than they do right now. In essence, they'll be giving Brandon Webb $8.5 million dollars with a blindfold on. And for a team on a budget that's asking a lot.

Reason #2: Public Relations 101. This team doesn't have a whole lot of equity with their fan base. 90 wins became 90 losses in two years. I wish I could tell you how many fans (and I'm not talking about garden variety, wishy-washy fans, but hard-core fans) who have told me the sight of Brandon Webb pitching for someone else will be cause to give up on this team for good. Saying goodbye (choosing to say goodbye) to a homegrown talent like Webb will irritate a fan base that is like a loose tooth, hanging by a thread.

(It should be noted there were many fans who felt exactly the same way when the D-backs cut Luis Gonzalez loose-that was one of those "look-the-bear-right-in-the-eye" type moments for Josh Byrnes and he nailed it)

Reason #3: What are you afraid of? Most fans are afraid of this scenario: Brandon Webb is bought out, signs with….I don't know….the Dodgers. He's the Brandon Webb of 2007, wins 20 and leads the Dodgers to a division title. Scary, right? You know what I think the organization is afraid of? That they pick up the option, and Webb gets hurt. Webb isn't the same. Webb can only give them 15 starts next year. $8.5 million for 15 starts doesn't sound so hot does it? When you're in the financial position the D-backs are, you can't give out money based on what a guy did for you. It's about what he'll do for you….now…..today.

Reason #4: The Power of Perception. If the D-backs are going to convince their fan base that this team is close to contending next year, it's a much easier idea to sell with Webb on board. Fans will buy into the notion of two great starters (Webb and Haren), a strong closer (Qualls) and an ever-improving Upton/Reynolds/Montero trifecta. Take Webb out of the equation, and replace him with any of the names available in free agency (with the possible exception of John Lackey) and I don't think fans will buy the "we're-this-close" speech.