The Great Gamble: Chicago's Kenny Williams Swings for the Fences

On Friday, the Chicago White Sox jumped from off the radar to the headlines in the last 45 minutes before the non-waiver trade deadline, when they (again) pulled off a deal for one of the top starting pitchers in baseball, Jake Peavy.

Chicago's General Manager, Kenny Williams, sent four of his top pitching prospects to San Diego for Peavy, who hasn't pitched since the beginning of June. He is scheduled to throw off a mound for the first time in eight weeks Saturday.

This is a deal that might merit poker champion Phil Helmuth complimenting Williams' stones; this is an enormous gamble.

There are a couple levels on which this deal is a substantial risk for the White Sox, only one of which involves Peavy's performance on the mound. Whether or not Williams gets Peavy onto the rubber this season has not yet been determined, but Peavy himself indicated he plans on being ready for game action by the end of August.

Whether or not Peavy pitches this season is arguably the biggest gamble Williams is taking with this deal. The White Sox have too much at stake to not get anything out of arguably their best pitcher in a season that might be the end of their championship window.

The Sox have a veteran roster made up of quality players with short term contracts. If Peavy doesn't pay dividends in 2009, there's a good chance he'll be pitching for a vastly different White Sox team in 2010 than he accepted a trade to play with this season.

The following players have contracts that expire after 2009: Jim Thome, Jermaine Dye (mutual option for $12M), Scott Podsednik, Octavio Dotel, Jose Contreras, Bartolo Colon, Ramon Castro and DJ Carrasco.

If you ignore the final three pitchers on that list, you're looking at two bats in the middle of the Sox order, their leadoff man, and one of their key setup guys potentially leaving town this winter.

After 2010, the following players will be free agents: Paul Konerko, Dye (if his option is picked up), and AJ Pierzynski.

The aging bats on this Sox roster have a realistic window of between two and 15 months together to make something special happen in Chicago. Considering the money these guys are making, it's highly unlikely the Sox will bring many, if any, of them back once their contracts come due.

Meanwhile, players like John Danks, Carlos Quentin and Bobby Jenks all have running arbitration clocks, meaning their salaries stand to grow significantly over the next few years.

Williams has quietly done a magnificent job of mixing a youth movement in between the solid veterans on this lineup over the past four seasons and remaining competitive. He's been able to replace players like Aaron Rowand and Joe Crede with youngsters either from within the organization or trade to keep the flow of the team rolling forward.

This mixing of the youth and veterans is the second piece of the gamble Williams is taking, though. The White Sox have four outstanding starting pitchers now in Peavy, Mark Buehrle, Danks and Gavin Floyd. Peavy, Buehrle, and Floyd are all locked up until at least the end of 2011, and Danks will probably get his this winter.

But in moving the four young pitchers the Sox did in this deal, especially Richard and Poreda, the Sox are undercutting their internal ability to replenish their bullpen and the back end of their rotation moving forward.

Richard and Poreda are both big, strong lefties that can hit the mid 90s with their fastball, something most organizations wish they could have in just one pitcher. The Sox had both of these kids and Matt Thornton.

Down the road, whether any of these kids becomes a legit major league starter or reliever is well in the future. But the immediate take away is cost effective depth in the bullpen.

The third level on which this is an enormous gamble circles back to 2009, much like the first point. But this is an external gamble.

As the trade deadline passed on Friday, the American League Central was the most active division in baseball. Detroit added Jarrod Washburn to their rotation, and the Twins brought in former-White Sox shortstop Orlando Cabrera.

The top teams in the division got immediately better. The White Sox, however, will probably have to wait a month to begin feeling the returns on this blockbuster.

There this is a gamble is on two separate planes. First, Detroit went out and got a stud starter that's going to step into the top of their rotation between Justin Verlander and Edwin Jackson immediately. The last time I checked, Detroit is the team sitting in first place, that the White Sox have to catch to get into the playoffs. They just got better.

The second plane on which this gamble takes shape is that the Sox are going to roll the dice and, using off days, essentially try to make it through August on a four-man rotation.

Because Colon has been bad, Contreras inconsistent, and the Sox aren't confident Freddy Garcia's ready to jump back into a playoff race from his rehab in the minors, this could tax the bullpen and the starters too much before the important games of September get here.

So, in review, Williams is really exposing himself and taking an enormous gamble in trading for Peavy.

When this deal is placed into the context of a diminishing window of opportunity because of expiring veteran contracts, especially in light of the division leading Tigers getting better immediately and Peavy not being ready to pitch for a month, the crucial final two months of 2009 are now clouded with uncertainty.

Additionally, the Sox gave up some really good young pitchers that not only take away from their overall organizational depth, but also runs the risk that Williams gave away a future star.

Peavy's expensive, but his track record indicates he's worth the money (and prospects). Whether or not this deal brings more jewelry to Chicago's South Side is a story that will develop between now and November, but this deal will go a long way in writing it.