Originally written on Midwest Sports Fans  |  Last updated 11/15/14

Say what you want about White Sox GM Kenny Williams, but the one thing everyone can agree on is that he is aggressive.

White Sox fans have to like that.

Chicago White Sox General Manager Ken Williams. Photo courtesy MLB.com

Year in and year out you hear the White Sox among the list of teams going after some of the market’s biggest names. We’ve seen it happen before, whether it’s Jake Peavy, Alex Rios, Ken Griffey Jr., Manny Ramirez, Edwin Jackson, Freddy Garcia, or any others.

Kenny Williams is clearly not afraid to make a statement in-season.

So far this season, the White Sox have already gone out and gotten Brett Myers and Kevin Youkilis, indicating that Williams is, once again, “all in.”

The only question left to answer now is: will KW bring in a high-end starting pitcher before Tuesday’s trade deadline?

To answer this question, let’s first go over what we know:

1. White Sox will go big or go home

Williams has gone on record saying that it wouldn’t make sense to go after a mid-level starter on the market. They already have guys that fit that mold (Floyd, Humber, possibly Quintana).

Earlier in the season, I wrote about exactly this. Someone like a Paul Maholm (for example, who the Cubs are reportedly shopping) would not put the team over the edge.

If they do get a pitcher, it’ll be a top-notch arm.

2. Greinke is option 1 and 1a

The Sox are pushing hard for Zack Greinke. Since Cole Hamels signed with the Phillies a couple of days ago, Greinke has been labeled the clear-cut best arm on the market.

And even before that happened, the Sox wanted him. They like his youth, his nasty stuff, and the fact that he’s been successful in the American League before.

3. And Greinke is as good as gone from Milwaukee

Brewers’ GM Doug Melvin said that Greinke will be moved. You can assume it’s now just a matter of mustering up a good enough offer for Milwaukee to accept.

4. There are alternatives

The high-end starters possibly on the market are Felix Hernandez, Zack Greinke, Cliff Lee, Josh Johnson, Ryan Dempster, and then Matt Garza & Edison Volquez, who are probably a tier below the rest of that group.

Most experts have been hesitant to put the White Sox as front-runners for any of these guys due to their lack of prospects. But this dilemma is something that Kenny Williams has been able to overcome in the past, and I’m confident he’ll be able to do so again.

Meaning if he really wants to make a deal, he will.

The White Sox could sell other organizations on prospects like southpaws Pedro Hernandez or Charlie Leesman, and outfielders like Jared Mitchell or Trayce Thompson. And those are just examples. Big league contributors could be dealt as well.

Greinke overcame his social anxiety disorder with a Cy Young Award in ’09 while with KC

The point is that they do have a system full of young ball players, and I’m sure KW can find ones that other GM’s will be plenty interested in.

The thing to remember about Kenny Williams is that he rarely makes the deal that had already been talked about a lot or expected from the fan base. He usually flies under the radar and pulls of something rather unexpected.

Now, this wasn’t the case when he acquired Kevin Youkilis in June (which made me look like a fool), which is why I wouldn’t put acquiring Greinke past him. But don’t forget about the other biggest names, Felix Hernandez and Cliff Lee. With KW, you never can rule anyone out.

It’s hard to acquire someone of such high stature, though…I know. That’s exactly why I don’t want to say that White Sox fans should expect someone so highly coveted to be added in the next few days.

But no one saw Adam Dunn coming, nobody predicted Jake Peavy being acquired for two of the organization’s best prospects (Clayton Richard and Aaron Poreda), and I can’t remember anyone who thought the Sox had enough to get Freddy Garcia in ’04.

Ken Williams has done it before, and if he really wants to, he does have the ability to do it again.


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