Top Five: Cubs/Sox Deadline Deals Of The Decade (And How They Compare To This Year)

With the 2010 trade deadline in the history books, Cubs fans and Sox fans alike can do little but sit back and wait to see whether the players acquired will help or hurt their respective teams. So, as the South Siders continue to contend and the North Siders play out the string, we compare this year's late-July swaps to those of the previous decade. That's the topic of this week's "Top Five."

For the big league ballclubs on both sides of town, the July 31, 2010 nonwaiver trade deadline has passed. Now that the dust has cleared and the tweets have slowed, we know a couple things: 1) Los Angeles Dodgers GM Ned Colletti really wanted someone to go fishing with and, 2) White Sox GM Kenny Williams still believes in second baseman Gordon Beckham. Oh, and we know one more thing as well: The second decade of the 21st Century was kicked off with a couple fairly interesting, if not difference making, deadline deals.

On the South Side, the first place White Sox traded their highest ranked pitching prospect, Daniel Hudson, to the Arizona Diamondbacks for a somewhat more seasoned pitcher, Edwin Jackson. (The Sox also included lefty David Holmberg.) At the time the trade went down, many thought it was a mere precursor to a larger deal to acquire perhaps the most coveted slugger on the market – Adam Dunn. But that never happened. So now the Sox move forward with Jackson, who’s with his fifth major league team and apparently well on his way to journeyman status (despite throwing a rather dubious no-hitter earlier this season).

On the North Side, the tragically flawed and foundering Chicago Cubs traded two beloved players — left-handed starting pitcher Ted Lilly and shortstop/second baseman Ryan Theriot (OK, he was beloved and belittled) — to the Los Angeles Dodgers for young second/third baseman Blake DeWitt and minor league pitchers Kyle Smit and Brett Wallach. Generally, most pundits have viewed the deal positively. Although the Cubs sent $2.5 million to L.A., the trade brings the team some salary relief for next season as well as two decent minor league arms and an MLB-ready second baseman who’s six years younger than the departing Theriot.

The question we’d like to answer this week is: How do these two trades compare to the big deadline deals of the previous decade? Let’s find out. Here are our Top Five late-July trades of the 2000s along with a simple "Win, lose or draw" comparison to this year’s swaps. If the trade in question "wins," it's better than either team's 2010 deal; if it loses, it's worse; and a draw is, well, a draw.

1. The Fleecing Of The Bucs

What’s the deal? In July of 2003, Cubs GM Jim Hendry made a modest proposal to the Pittsburgh Pirates who, as they seem to do every year, were in the process of trying to shed salary following another dismal first half. "Give me your slow-footed, power-hitting third baseman Aramis Ramirez," said Hendry (in so many words). "That’ll save you a $6 million salary, which will surely be subject to inflation in future years."

Hendry also asked for fleet-footed centerfielder Kenny Lofton, whom the team needed after losing top prospect Corey Patterson to injury. The Pirates GM, Dave Littlefield, agreed — as long as the Cubs gave up infielder Jose Hernandez and two minor leaguers.

How’d that work out for ya? Quite well, thank you. Aramis Ramirez has gone on to become one of the top third basemen in the National League and certainly the best Cubs third baseman since should-be Hall of Famer Ron Santo. He’s been at least a 4 WAR player every season until the last two: Last year, he missed significant time because of horrible shoulder injury and, this year, well, a nagging thumb and wandering eye at the plate has reduced him to a replacement-level player.

Win, lose or draw? Win. Probably. It appears doubtful that the power-challenged DeWitt will ever surpass Ramirez in value, though it’s not out of question that the 24-year-old could go on to become a solid second baseman (and backup third baseman) for the next few seasons. Ultimately, the Aramis Ramirez trade will likely always remain the crown jewel in Jim Hendry's, uh, crown.

2. Countering CC

What’s the deal? In 2008, with the Cubs leading the NL Central, Jim Hendry found himself on the defensive when the rival Milwaukee Brewers acquired ace lefty CC Sabathia from the Cleveland Indians. So, on July 8, the Cubs GM dialed up the legendary Billy Beane in Oakland and swung a deal that sent outfielder Matt Murton, infielder Eric Patterson and catcher Josh Donaldson to the Athletics for oft-injured strikeout artist Rich Harden and swingman Chad Gaudin.

How’d that work out of ya? Meh, not bad. Harden’s 2008 numbers still look very impressive (2.07 ERA, 2.95 FIP, 3.55 xFIP; 11.01 K/9) and he was a 2.7 WAR pitcher for the Cubs that season. Of course, by the time Harden made it into the 2008 postseason, the team’s wretched fate was already almost sealed, being down 2-0 to the Los Angeles Dodgers. And, while his 4.1 innings pitched in that playoff game were perhaps serviceable (3 ER, 5 H, 3 BB, 4 K), they were hardly dominant. Harden did go on to give the Cubs 26 starts with decent if, again, not exactly dominant' results in 2009.

Win, lose or draw? Win. Granted, in retrospect, the Harden acquisition provided more of a morale uplift than a baseball one. But it was an uplift — and a great trade — nonetheless. In a spectacular regular season, when contention was not a dream but a glorious reality, the Cubs made a move that shook the baseball world to its core and surely sent a chill across the frosty mugs of Milwaukee. Alas, it proved to be a dream as fragile as Rich Harden’s right arm.

Will Blake DeWitt provide the team with more value than Rich Harden (oh, and Chad Gaudin — I’ve been conveniently ignoring him, haven’t I)? If he plays up to his No. 1 draft pick potential and sticks around long enough, he just might. And, who knows, maybe Brett Wallach will make his way to the big leagues and be a productive starting pitcher for a number of seasons as well. But, as things appear right now, the drama of the Harden trade still makes it a winner.

3. Finally, Peavy

What’s the deal? Just last year, at the buzzer, White Sox GM pulled off the trade that had been haunting Chicago’s newspapers, blogs, airwaves and cable TV connections for months (albeit mostly on the other side of town). To the San Diego Padres went pitching prospects Clayton Richard, Aaron Poreda, Dexter Carter, and Adam Russell. To the White Sox came one Jacob Edward Peavy.

How’d that work out for ya? Eh, not so good. At least not yet. When he was acquired, Jake Peavy was recovering from a strained tendon in his ankle. He did manage to make three starts for the White Sox in 2009, but the team finished third in the AL Central and didn’t make the playoffs.

This season, Peavy made 17 starts with the White Sox with respectable and improving numbers (107 IP, 4.63 ERA, 4.05 FIP, 4.12 xFIP) before going down for the season with a completely detached latissimus dorsi (back) muscle. Perhaps ironically, the Sox have been in first place for most of the second half of the season thus far and could very well win the AL Central and a playoff spot.

Win, lose or draw? I’m calling it a draw. Edwin Jackson will likely never have a stellar 6+ WAR season like Jake Peavy did in 2007, but he’s three years younger and has pitched 30+ starts in each of the last three seasons. Peavy has now had two crippling injuries in back-to-back years, and it’s hard to say whether the White Sox will ever get much value out of him — especially given his high price tag. If Peavy does come back, he could easily outpitch Jackson for the remainder of his deal.

4. We Got Nomah?!

What’s the deal? The year: 2004. The Cubs: Somehow both struggling and successful. With names such as Sosa, Alou, Maddux, Prior and Wood, that ’04 squad didn’t lack star power. What it lacked was consistency, winning consistency.

In an effort to give the team the electric jolt it needed — and a little more star power — GM Jim Hendry worked a dazzling three-way deal that sent Cubs pitching prospect Justin Jones to the Minnesota Twins for first baseman Doug Mientkiewicz. Hendry then gathered Mientkiewicz, shortstop Alex Gonzalez (who never recovered from his awful 2003 NLCS defensive error) and two Triple-A players, tied them up with a red ribbon, and sent them to the Boston Red Sox for the man with the wristbands: All-Star shortstop Nomar Garciaparra (and eventual fan favorite Matt Murton, whose fate is noted above).

How’d that work out for ya? Um, yeah, not too well. Nomar hobbled through the remainder of that season battling wrist and groin injuries. Meanwhile, the Cubs crashed and burned, losing a crushing series to the New York Mets and failing to secure a Wild Card spot, their only chance at the postseason.

For the following year, Nomar signed a one-year deal with the Cubs and lit up the already-bright Arizona skies with a stupendous spring training offensive display. But, once actual play began, he got off to a slow start and then suffered a painful groin injury on live television in late April. He’d go on to play in only 43 games for the disappointing 2005 Cubs, hitting for an approximately league average wOBA of .333 and providing only 0.4 WAR.

Win, lose or draw? Lose. I just can’t apply the "morale uplift" theory to the Nomar deal. As exciting as that first day or week was, Garciaparra didn’t do much to help the Cubs overcome what had to be among the most ignominious winning seasons in baseball history. And he did little to nothing for the team in 2005.

Blake DeWitt will almost certainly never be the hitter that Nomar was at his peak but, assuming he stays healthy, DeWitt’s youth and solid fundamentals should prove a decent value to the team over the next couple to few seasons. And either or both of the minor league pitchers that the Cubs acquired from the Dodgers can only add to that value. All told, these guys will likely do more for the Cubs than Nomah ever did.

5. A Blum Deal

What’s the deal? In 2005, with slim pickings on the trade market, White Sox GM Kenny Williams held fast for the most part (sound familiar?) and made only one minor move: acquiring veteran infielder Geoff Blum from the San Diego Padres for minor league pitcher Ryan Meaux.

How’d that work out of ya? On first blush, the Blum deal was practically negligible. He had only 99 plate appearances with the team that season and actually provided a negative WAR (-0.3). That essentially means the Sox would’ve been better off not making the trade and giving one of their Triple-A players that bench spot.

Or does it? In Game Three of the 2005 World Series, Blum hit a home run in the top of the 14th inning to give the visiting White Sox a lead over the Houston Astros. The Sox would go on to win the game and, in case you’re just emerging from a coma, the championship.

Win, lose or draw? WIN. Come on, the guy got a game-winning knock for the White Sox in the World freakin’ Series! Which just goes to show — it doesn’t always boil down to a guy’s WAR. Sometimes good luck and a sweet swing can make even the smallest trade deadline deal pay off in a big, big way.

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