Prime time at the trade deadline

Like a lot of Don Draper wannabes, I'm more than a little excited for the "Mad Men" season premiere this Sunday night.

Unfortunately for me, the rare man without a DVR, I'll be at a live taping of the critically panned Chicago show "Mad Fans," starring the 39,000 or so Cubs fans who pay big bucks to watch a bad team.

I'll also be missing the second episode of the reality show featuring those other "mad men," Ozzie Guillen and Kenny Williams. "The Club" will be airing its second episode this Sunday as a lead-in to a great night of television

The MLB Network's reality-based show about the inner workings of the White Sox airs before the AMC hit, not to mention America's favorite show about nothing, "Entourage."

Maybe if I'm nice, Cardinals manager Tony La Russa will let me watch Draper and the gang in his spartan office. Sure, and maybe he won't wear sunglasses for the ESPN night game.

I suppose I'll have to catch "The Club" another time; it's not as if I'm missing anything current. (My wife calls the show, "Remember What Happened Six Months Ago?")

I liked the first episode, and I enjoy the participants, but surely, the biggest problem with the show, besides the hilariously staged scenes (Bud and Jerry kibitzing in the Phoenix deli slayed me), is the timing. Unlike HBO's "Hard Knocks," which airs very close to real time, the show's lag time hurts its value. Of course, as the Sox GM would say, "That's not a Kenny Williams problem." It's just a fact.

After all, wouldn't you like to have cameras focused on "Ready-For-My-Close-Up" Williams this week, and get to watch it after the July 31 no-waiver trade deadline passes?

I know I would.

For both the White Sox and the Cubs, the next week of prospective wheeling-and-dealing could have major impacts on the future of their franchises. While the first-place Sox are trying to win now without mortgaging the future, the fourth-place Cubs need to prepare for tomorrow.

The spotlight is once again on Williams, a situation he surely doesn't mind.

Williams is so famous for bluffing about his interests that he's almost like an actor in his own TV show. (Oh wait, that's kind of true now ...)

Williams was at his all-time B.S.-ing best last year, trying to lull fans into thinking he wasn't going to make a blockbuster move.

In early July 2009, with the Sox within striking distance of Detroit for the AL Central lead, Williams proffered this warning about the team's inability to
enter the trade market:

"Well, if I'm being completely honest, money is more of the issue now. We expected a little more support than we've gotten," he said back then. "I think it's a reflection upon the economy of what's kind of happened with regards to attendance and I don't know if we've played consistent enough, or been exciting enough for people to get behind us. We're still hopeful."

At the time, the Sox were averaging a little more than 26,000 fans a game and a weekday series against the Dodgers barely cracked the 20K mark.

And what did Williams do? Oh, not much, except pick up Jake Peavy and Alex Rios, who are making a combined $24.7 million in salary this year. Peavy, of course, is out for the season, with a rare muscle tear in his posterior shoulder. Rios has been one of the best all-around players in baseball.

This year, with the Sox drawing around the same, Williams is up to his old tricks, telling beat writers in Seattle that he "doesn't see anything materializing." Though, this time he's not crying poverty.

"If I'm being honest and completely transparent right now of the price that is being asked for some of the players that we've inquired about, for us, it's more detrimental to our present and our future than we'd like," Williams told reporters a few days ago. "We'll see how that develops."

You know what that means: If you were Daniel Hudson, you wouldn't start looking at Chicago real estate just yet. Young homegrown pitchers are valuable bargaining chips for Trader Kenny, with Brandon McCarthy, Gio Gonzalez (twice), Clayton Richard and Aaron Poreda all exiles from the South Side.

Hudson might be a future star, or he could be another pitcher the Sox promoted as a way to raise his value. Williams hasn't been burned too badly by the young arms he's given up, has he?

The big question is, can the Sox add to this year's team without giving up an important player like Gordon Beckham, who has all-but-erased his miserable
start with a solid approach at the plate that has him looking like the doubles machine of last year.

If the Sox are adamant about getting a big left-handed hitter like Prince Fielder or Adam Dunn, who are big in the literal and figurative sense, would Williams bite on moving Carlos Quentin, or be able to sell Quentin as a viable alternative to Beckham? I would, but I'm not Trader Jon.

For a team that has at times struggled on offense, Quentin has been a beast at producing runs. After starting slow, like his team, at the plate, he's heated up as well, and currently has 64 RBIs in 271 at-bats. He's improved his batting average 15 points this month, from .229 at the end of June to .244 currently, and he's hitting .375 with runners in scoring position. Quentin is unquestionably a major talent.

The problem, of course, is he's consistently nagged by injuries, which is how the Sox got him in the first place. He crowds the plate and pays the price, recently missing the Seattle series with a bruised hand. But he has managed to appear in 79 of 94 games, and he could be a bargaining chip for teams like
Milwaukee or Washington, or at the very least a player who could be traded again to another contender for more prospects.

I'm in favor of moving Quentin simply because of the unpredictability of his career. One day he's bashing home runs (19 this year) and the next he's taking himself out of the lineup in a fit of pique (2008's infamous bat-smacking episode). Is his potential worth the headaches?

Conversely, for what he can do on the field, Quentin is still pretty cheap. He's coming into his second year of being arbitration eligible, having signed for $3.2 million last year. If he finishes with comparable numbers, he's due for a raise, but he's still under the club's control for two more years. Given his up-and-down history, you wonder if he'd be willing to reconsider signing a multiyear deal for security, like Gavin Floyd did before last season.

Would you trade Quentin for Dunn? It's a question that has been brought up in the press box, if not in the stands. Dunn is a little older, a liability in the outfield and likely a short-term rental, but at 30, he's a known commodity. He would also fit right into the Sox's loose clubhouse culture. All indications are that the Sox wouldn't part with either Beckham or Quentin, both cheap for their production. But then again, Williams has been known to bluff.

Maybe Williams is right this year. Maybe the only market that's open is his bar. I doubt it.

I've made it nearly 1,000 words without talking about the Cubs' trade possibilities. Can Jim Hendry get some prospects for Ted Lilly or Derrek Lee? Is he skittish on letting go of Lee, the mainstay of the post-2003 club? Could he cut a little more salary for next year by dealing Ryan Theriot and/or Xavier Nady? Will he help out a friendly GM now in order to grease the wheels for a Carlos Zambrano deal this winter?

Hendry is accustomed to adding difference-makers, not dealing them, so it's hard to judge his track record in these situations. If he's sentimental about keeping his veterans to play out the stretch, I'd point him to a line from the leading character of "Mad Men," Draper: "There is no American history, there is only a frontier."

As in, let's move away from the past and start building for the future.

Now that he has job security, after Tom Ricketts' assurance that Hendry isn't getting fired in the wake of Lou Piniella's impending retirement, Hendry should be concerned with cutting salary so he can have the flexibility to add this offseason.

While Williams readies for another reality show episode espousing his philosophies, I'm sure Hendry is glad the cameras are somewhere else.

Jon Greenberg is a columnist for ESPNChicago.com. You can follow him on Twitter at twitter.com/espnchijon.