A couple of years ago, I participated in a 2006 season preview with Aaron Gleeman (now of NBC Sports), Bryan Smith (now featured on SI.com), and Rich Lederer over at Baseball Analysts. I bring this up because we touched on a number of issues which suddenly seem more pertinent. Chief among those issues was the (possible) White Sox transition into a large market ($100+MM payroll) club, the depletion of their farm system, and what those two things could mean in an increasingly competitive AL Central.

I've been thinking about that conversation a lot tonight. Looking back, there isn't a singular quote which is incredibly relevant on its own, but the general points brought up, especially in the Sox portion of the discussion, still ring true.

The part of the conversation I remember most, however, was Gleeman's assertion that any AL Central team willing to spend $100+MM year-in-year-out would be perennial favorites. He was talking about the White Sox, but I wondered (to myself) what a Detroit team, which had just vowed to spend 'as much money as it takes,' and a Cleveland team with a revitalized fan base could do.

So here we sit, almost a full two years later. The White Sox farm system seems destined to be named the 29th best (2nd worst) in all of baseball. And thanks to some dubious extensions and pretty terrible middle relief signing, the only thing about the White Sox which could be considered Big Market is their payroll.

• The White Sox are unwilling to pay over slot in the first-year player draft.
• The White Sox are (seemingly) afraid to offer arbitration to departing free agents. (Perhaps to help limit draft costs.) The last time they had multiple extra picks thanks to arbitration they got top prospects Josh Fields and Gio Gonzalez, who fell due to unfounded character concerns. The rest of the draft was filled with overdrafts who would sign below slot (Wes Whisler, Dony Lucy, Ray Liotta.)
• The White Sox have been unwilling to compete for high-dollar amateur international talent, with the SS Silveiro marking their only $300+K signing of the last 5+(?) years.
• The White Sox have been unwilling to feel the wrath of the Winners Curse by shelling out top dollar to the top free agents. There hasn't been a singing of a true top-level free-agent since Albert Belle almost 10 years ago. And I haven't even brought up the name Scott Boras yet.

Gleeman was wrong. $100M doesn't go as far as it used to. The Sox outspent the division to a 4th place finish last year, and they appear to be headed to another $100M 4th or 5th place finish this year.

Gleeman was right. You need only look as far as the Tigers to see how a properly run Big Market club should operate.

• They've invested heavily in the amateur international market
  
• They've refused to bow to Bud Selig's slotting demands in the June draft.
  
• They've overspent when necessary on the free-agent market.

The Tigers acquisition of Cabrera doesn't effect the Sox as much as it initially seems. Most people around here (myself included) were extremely skeptical about the White Sox ability to make the playoffs this year. I would have put them slightly better than 5% chance to win the AL Central yesterday. The Cabrera trade takes it down under 5%, but I'd hardly call that a difference at all. Our long-shot is now a slightly longer shot.

More than the 2% change in the Sox playoff chances, this trade gives a glimpse into what could have been had the Sox truly taken the influx of new fans derived from 2005 World Series run and put those dollars to use in every way possible. Simply put, the Sox missed out on their "big fish" because they refused to spend enough money on bait.

That hurts.