At age 6, I had my first best friend. I do not remember why I was chosen as companion and owner of this particular Teddy Ruxpin, but he was mine. This robot-bear existed solely to read children’s stories via a tape player tucked in his stomach pouch. But it was easy for me, a wallflower with a stuffed animal obsession, to relate to the animatronic bear on a deeper level. I would rewind his cassette tape with a No. 2 pencil, surgically insert the tape into his stomach pouch, secure the Velcro, and we’d talk. He told me stories, stories I knew by heart, that six-year old me looked forward to more than most things— including, but not limited to, reruns of M*A*S*H, tee ball practice, and riding my Cabbage Patch Big Wheel.

What I do remember is a value that was instilled in me long before Mr. Ruxpin came to live with my family: Taking care of oneself and one’s possessions was of utmost importance. Caring for everything, even toys, was a reflection of something larger. It was indicative of a certain self-possession that always seemed important. Fortunately, caring for Teddy was easy.

That is, until I killed him.

No jury would convict me of homicide, as it was an honest mistake. I could plead to a lesser conviction of manslaughter due to ignorance with the best intentions. One day, during story time with Teddy Ruxpin, my mother said I should take a bath. Not wanting to interrupt the story, and knowing the importance of good hygiene, I took the bear with me. The talking bear perched on the edge of the tub, entertaining me as I washed his hair and twirled the tufts of synthetic fur with my fingers, giving him a fresh look. Then, I put him in the tub to soak.

There were warning signs Teddy Ruxpin was drowning, but I could not see them. He sounded relaxed as he read the book, the tape player’s mechanics flooding with water. His mouth continued to move, slowing, as grinding noises escaped from the space where his brain should be. Looking back, I am thankful that my best friend wasn’t a toaster oven or FM radio that required electricity instead of batteries.

While I don’t remember exactly when I was given my Teddy Ruxpin, I do know when Kenny Williams received his: Oct. 26, 2005. It was a gift from his 40-man roster, but more specifically Jermaine Dye, who hit a groundball single to center field scoring Willie Harris in the eighth inning of Game 4 of the 2005 World Series. Instead of a bear, Williams’ treasured gift was the prestige that comes from building a World Series champion.  But Williams has not done a particularly good job of caring for this honor, and the White Sox have spent the past half-dozen seasons flip-flopping between tepid success and clear failure because of weak decisions, non-activity, and some bad luck. Williams’ prestige is gasping. 

The 2006-2007 off-season was his first crucial opportunity. Key members of the championship club – half the lineup, half the rotation — were set to hit free agency in 2007 and 2008, and Chicago’s competitive window was closing quickly. Leverage those expiring contracts for the long term, or push for one last hurrah with that core? Williams did neither. The trade of Freddy Garcia for Gio Gonzalez and Gavin Floyd was his only significant move, as detailed in the 2007 Baseball Prospectus annual:

Even if the Sox can stave off the ravages of age and injuries, the ravages of free agency may become a problem much sooner. Whether by foresight or happenstance, the Sox went into the 2006-2007 off-season with every significant contributor under contract for another year. But Vazquez, Buehrle, Dye, and Podsednik are all free agents after 2007; Garland, Pierzynski, Uribe, and Crede follow in 2008.  In two years, the Sox will be in a position where they will have to either re-sign or replace over half their starting rotation and over half their lineup.

Unfortunately, a farm system that was considered one of the best in baseball a few years ago has been depleted. Meanwhile, their AL Central brethren have become increasingly stacked. By 2009 the Sox may be struggling just to stay out of the division cellar. If the Sox are to duck this fate, the time to strike is now, which is what makes Chicago’s sole significant winter move, trading Freddy Garcia for Gio Gonzalez and Gavin Floyd, so perplexing. It’s not that Gonzalez and Floyd don’t represent a reasonable haul for a pitcher a year away from free agency, it’s that stockpiling minor leaguers for the future should not be the team’s highest priority.  The priority should be to maximize the talent on the field this year and next and finding solutions for the sub-optimal production they’re getting at multiple lineup positions, particularly left field.  Kenny Williams had the enviable position of having starting pitching to trade in a market that has overvalued even mediocre pitchers.  Instead of using that excess to place a better team on the field this year, he punted the advantage to a future which may or may not involve a competitive Sox team.

If 2007’s off-season decisions were akin to washing Teddy Ruxpin’s hair on the edge of the tub, decisions made mid-campaign in 2009 were the bear’s death by drowning. Williams acted aggressively to pursue the division-leading Tigers, who were up by just 1.5 games at the trade deadline. First base prospect Brandon Allen went to the Diamondbacks for middle reliever Tony Pena. Brian Anderson went to the Red Sox for Mark Kotsay in a swap of outfielders. Four prospects, including pitcher Clayton Richard, went to the Padres for pitcher Jake Peavy; Peavy was on the disabled list at the time and, though acquired in July, would not make his White Sox debut until September. Finally, Williams claimed slumping outfielder Alex Rios from the Blue Jays Aug. 10, accepting more than $60 million in salary obligations in the process. But Williams had overestimated the strength of a team that had been hovering around .500; even with the trades, Chicago went 26-32 after the deadline, finishing a distant third.

The effects of that doomed push are still apparent in Chicago’s depleted farm system and the large, immovable contracts attached to Rios and Peavy, who were more than one fifth of the total payroll last season.  

The pattern of dealing prospects before they have provided value continues to haunt the White Sox. Players like Gio Gonzalez, Chris Getz, and Chris Young were traded before they had an opportunity to prove themselves one way or the other. They didn’t just trade prospects; they traded their only prospects at any given moment, so they filled holes while opening new ones. The Jake Peavy trade is particularly devastating in this regard; the White Sox went all in (giving up Dexter Carter, Aaron Poreda, Clayton Richard, and Adam Russell) on an expensive pitcher who would make just three starts for Chicago that year, and 38 in three years.  In a 2009 article, Christina Kahrl raised the argument that even if Williams was overreaching at the time, this was a trade for the future and a gamble that could have been redeemed by Peavy’s performance, but it was not to be. While there have been a few notable moves that proved successful (Joe Borchard for Matt Thornton and Chris Carter for Carlos Quentin come to mind), the propensity to deal prospects early, compounded by an extremely poor series of drafts, has left the White Sox with a weak system for little return.

This off-season, Williams had an opportunity to put the tape back in Teddy Ruxpin to see if there was any life left. Entering the 2012 off-season with a rebuilding mindset, the White Sox showed an interest in moving several players, including Quentin, Floyd, and John Danks. It became evident from the Sergio Santos trade that more players might be on the block, as well. But even though Danks and Floyd garnered interest this off-season, they remain with the White Sox; Williams was not satisfied with the offers, leaving the 2012 offseason looking a lot like 2007’s indecisive winter.

That dead bear haunted me, because I kept his corpse. I let him rest, in the toy box among the Pound Puppies and the Glo Worm, hoping he would miraculously recover. Occasionally I would tempt fate and stick a tape in his stomach, watching as my best friend showed intermittent signs of life, gasping for air before returning to his persistent vegetative state. Each time he died, it was a reminder that sometimes even best intentions are met with negative consequences, a reminder of why I can’t have nice things.

There may be some hope for Kenny Williams, however. If  Adam Dunn, Gordon Beckham, and Alex Rios are able to return to form after disappointing performances in 2011, there could be some life left in the team. If the White Sox find themselves in a buyer’s position in July, perhaps Williams has learned his lesson*, and will balance moves that strengthen the current roster with those that improve Chicago’s future.

*There is no evidence to show that Kenny Williams has ever taken a player in the bath tub, though the mental image of Kenny Williams, Adam Dunn, and an animatronic teddy bear bathing together was difficult to shake while writing this piece. 

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It seems to me that the general opinion of Kenny Williams has gone from bad to good to bad again. To be honest, I think all we should be able to agree on is that he has made a hell of a lot of moves, and enough have both worked out well and worked out poorly that we probably shouldn't put him too far on either end of the sucks-awesome scale, as fun as it is to do that.

At this point I think Kenny has made so many bad moves that letting him continue to run the team is akin to your parents giving you a toaster once they learned what happened to Teddy.
"That dead bear haunted me, because I kept his corpse. I let him rest, in the toy box among the Pound Puppies and the Glo Worm, hoping he would miraculously recover."

I originally was going to skip over this article, because I hadn't read you before.

Those two sentences alone made this article worth the read. Looking forward to reading more.
Thanks for bringing up the failed attempts to succeed by KW. Hudson and a young lefty Holmberg for Edwin Jackson? Need I say more? Please make it stop.
Williams has always seemed an enigma to me, so pairing him with a deceased toy bear is somehow appropriate. Well done, Cee.
Nice article, Cee--not only for the handy capsule review of Kenny Williams' follies and the great broken toy/crummy ballclub metaphor, but for allowing me to recover the memory of the hell I put my kid brother's own Teddy Ruxpin doll through back in the '80s. Playing Quiet Riot and Twisted Sister cassettes through it was probably insult enough; a darker note was struck when some friends and I inadvertently broke the snout right off of Teddy's face. Cursed with a family too poor to replace the bear, my brother was forced to be content listening to Teddy's stories emanate from a grotesque, Cylon-like hole in his visage. After reading this piece, I can connect that gaping wound with the awful pitching rotations Jim Bowden constructed for my Reds in the early '00s. Karma is served.