Prospectus Roundtable: Windy City Showdown Edition

Christina Kahrl: Given that both of these clubs made the postseason last October, and both of them are not in first place now, how disappointing has baseball been for Windy City fans, and what do you think each team should do about it?

William “Bil” Burke: My impression is that Cubs fans are handling things much better than Sox fans. Expectations were borderline ridiculous following the White Sox‘ 2008 “division title.” The 2008 team was a mediocre team in a bad division. In reality, with all the young Sox breaking out last year (Danks, Ramirez, Quentin, Floyd to name a few) it would be rather remarkable for them to all return to their 2008 levels (or dare I say be even better) in 2009. On the North Side, they did win 97 games, and while that also seemed unlikely to repeat, the Cubs are hanging around within striking distance, and the fan base seems much less panicky for the moment. Winning divisions hasn’t really been the magic elixir of playoff success for the recent Cub teams, so maybe a Wild Card spot would be just as well.

As for what these teams should do… the Cubs should sit tight and enjoy the recent uptick in offense from Derrek Lee and Geovany Soto. It looks like tonight Lou found himself with Soriano playing some second base; I like that kind of creativity. Now, if he could just move Soriano down out of the leadoff spot in the batting order, that would truly be something. Fukudome, despite his streakiness, still has an OBP over .400, and with Theriot and Lee hanging around .350, that would create a lot of RBI opportunities for the middle of the lineup (which would, in theory, contain Soriano). I think an interesting trade idea for the Cubs would be to acquire Josh Fields from the Sox. While Ramirez is out, he could platoon with Fontenot at third base, and if Soriano could really play some second, then Fields could continue platooning, but instead with Hoffpauir in left field, after Ramirez returns. This is not to say that Fields is some sort of championship solution to their offensive problems, but he should be able to mash lefties, and the price is probably right, as it should not take much to acquire him.

And why should it not take much to acquire him, you might ask? Well, to answer that we get to talk about “Ozzie’s Guys.” On the Sox, it seems, a player is either one of “Ozzie’s Guys” or he is not. We see that when you fall out of good graces with Ozzie, you are not long for the White Sox roster. Just ask Joe Crede, Frank Thomas, or Orlando Cabrera. I am not judging the quality of those decisions, just stating that when Ozzie is done with you, you are done with the Sox. Josh Fields is close to being done on the South Side.

Will Carroll: Almost exactly what he said. I think both teams are underperforming relative to their fans’ expectations, but at least in the case of the Sox they’re performing right on pace to PECOTA. The Sox are also an interesting case in that their inflexibility on the field is the complete opposite of Guillen and Williams, who’ll do anything to win. I think they have to be glad that they didn’t get Peavy, given his ankle injury, but I doubt many will notice. I’m surprised that Williams didn’t immediately go after other pitchers, but he’s never really been a Plan B guy-he’s bold, but seldom calculating, which is a blessing and a curse. Honestly, I wouldn’t be surprised if both of these teams became significantly better while standing pat. I’m not saying that they will, just that they could given the normal fluctuations of the season.

Christina Kahrl: I can’t say that I like what that would mean for the Cubs’ defense under what Bil proposes, but I’m inclined to agree with Will as far as the virtues of standing pat for both of these teams. Both are still in their respective division races, neither has to worry about a rival suddenly germinating into a 95-win team, and both have key players whose comebacks from injury would seem to make all the difference. But the strength of that agreement depends on a couple of ETAs: What are we looking at in terms of the returns of Carlos Quentin to Bridgeport and Aramis Ramirez to Wrigleyville? And while A-Ram’s return is a big factor, getting some shadow of the player formerly known as Geovany Soto would make a big difference.

Will Carroll: I think we’re looking at the All-Star Break for both on the positive side. Quentin’s injury is one that lingers and can cost years; credit some optimism to his having White Sox Head Trainer Herm Schneider running the rehab, but Quentin’s never stayed healthy for a full season, and is fast becoming the new J.D. Drew. Ramirez is a more interesting proposition in that, despite having a severe injury, once it’s healed, it’s usually healed fully. It should only affect him at the plate and even then, guys can play through it, especially if they’re willing to show some abandon (think B.J. Upton from the ’08 playoffs). I don’t think either pushes the team over the top, talent-wise, or that either team is going to need to fill in the apparent holes up the middle.

William Burke: I hope I didn’t somehow give the impression that I think the Sox are still a contender. This is a bad team, and I don’t think that they can somehow come from behind, even in a bad division. While it is impressive what the Sox training staff has been able to do over the last several years in terms of keeping players healthy, there are times when it seems like they are just keeping them good enough to play, as if the DL is supposed to be avoided like the plague. I don’t have any confidence that Quentin is going to ride back into action and rescue this lineup from the speedy goodness of Scott Podsednik and DeWayne Wise; push him to the 60-day DL, work him back to 100 percent, and get this team ready for 2010. That involves getting a plan about a center fielder and a third baseman (with Beckham heading to second base, and hopefully doing his best Chase Utley impersonation), and also going out and doing one of the things that I think Kenny Williams does a decent job of-re-stocking the bullpen. He’ll need it for the post-Jenks era.

The Sox should probably sell everything not tied down, and do it fast. If they wait, they could accidentally get too close to the division leader and then we’ll have a setting ripe for a repeat of the 1997 White Flag Trade. This is probably going to be the Beckham/Danks/Quentin team for a couple of years, and they should do what they can to fill in around those players with the types of players that can help that trio win multiple division titles over the next five years. I am not saying that Jenks, Thornton, Dye, Konerko, Thome, Pierzynski, or Buehrle cannot help those teams, but if they can get something for those guys now and save a few nickels in the process, that is probably for the best.

Christina Kahrl: I guess I disagree. There isn’t much about the Sox and a tear-down that I see delivering all that much value. Jim Thome‘s in his walk year, not that many AL contenders are looking for a DH, and Thome wouldn’t bring a ton of talent in return. Dealing Paul Konerko (signed through 2010 at $12 million per) would involve eating a lot of cash, and I don’t know if I believe Brandon Allen‘s the answer as to who takes Konerko’s place just yet. Dealing A.J. Pierzynski? Position scarcity would make him valuable, and it’s not all bad that he’s under contract through 2010 as well, but his deal comes with some no-trade protection, plus the other team would have to be willing to look past his native charm. Jose Contreras? I don’t think he’d fetch much, nor would Octavio Dotel. This is why I think we’re seeing the Bobby Jenks rumors, because that’s somebody who’d be the acquiring team’s property through 2011, and because premium relievers (or players perceived to be premium relievers) might be the ticket for getting value. Thornton and Linebrink could yield something because they’d also be under control through 2011.

I guess I’m left with the problem that, even if the Sox elect to tear down, there isn’t necessarily some bonanza of young talent awaiting them in the subsequent deals if they go that route. The Sox have already added a lot of young talent in the recent past-Quentin, Danks, Floyd, Alexei Ramirez, and Tyler Flowers, for example-so I guess I come back to the idea that they can follow the same playbook as last season: Go for it. They’re not that far out, and with the proposition that they could deal for an infielder and/or a center fielder, they might be able to help themselves plenty if they elect to take on a moderate amount of salary. In this division, fixing any one problem can make all the difference.

Will Carroll: With the Cubs, they’ve dealt with a lot of injuries and managed to keep within range of the division leaders. Part of that is the mediocrity of each division, but getting Aramis Ramirez and Rich Harden back will offer some boost. Jim Hendry won’t sit still again, and after getting Harden for a great return, no one’s complaining that he can’t trade with the big boys.

Christina Kahrl: Like Will, even with Peavy now off of the table, I guess I can’t shake the feeling that Hendry might gun for something big and noisy, but the problem is that with as many big-name players tied up with big-figure contracts, there really isn’t that much payroll and roster flexibility. Kevin, is there even enough talent there for the Cubs to swing a deal using prospects?

Kevin Goldstein: As far as the Cubs go, a month ago I would have said they’re totally screwed in the trade market; I’d have said they have no prospects except for Josh Vitters, who is practically untradeable, and then the disruption of the ownership situation really limits them financially. I do think some things have changed since then, though. I don’t really know what it is, but every time I turn around, I have some scout labeling a prospect in that system as some kind of sleeper. Guys barely on the radar-like shortstop Darwin Barney, catcher Steve Clevinder, and outfielder Jim Adducci-are suddenly getting noticed by scouts, not as studs, but at least as items of having value on the market in lesser deals for an extra arm or bat here and there, and teams are always going to look for athletic middle infielders like Starlin Castro and Junior Lake. I don’t think they have the chips to make a blockbuster, but I no longer think they’ll be totally shut out either.

As for the White Sox, almost suddenly they have a lot of interesting prospects. We’re getting glimpses of Gordon Beckham and Aaron Poreda right now, and they feel that they have their A.J. replacement in Flowers, and that Allen can take a Thome/Konerko spot in the not-so-distant future, while hoping Danks can end up in center. However, these guys are not ready to step in if a housecleaning happens this year, and 2010 could be really ugly, but sometimes you have to get worse before you get better.

William Burke: For the Sox, in the near future we should have the arrival of Jordan Danks to finally provide a real center fielder, Poreda just had a nice debut appearance, and you just mentioned Flowers. Filling in the corners and bullpen with under-appreciated talent should be right in Kenny’s wheelhouse (Dye, Quentin, Thornton, Jenks, etc.). It is correct to say that they could make yet another run with the old crew; heck, after bringing back Podzilla and the recent signing of Freddy Garcia to a minor league contract, we are just an Aaron Rowand trade away from putting the band back together! But allowing Kenny to try for it one more time is like watching the smoker who is trying to quit tell himself, “just one more pack and then I’ll stop, I promise”. As a Sox fan, I’m plenty content with the World Series in 2005, if they need to hit the reset button or go cold turkey, I can accept that; I even encourage it.

A version of this story originally appeared on ESPN Insider .