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Wisch: The 5 Worst Trades In Chicago Baseball History

Starlin Castro. (Photo by Justin K. Aller/Getty Images)

Starlin Castro. (Photo by Justin K. Aller/Getty Images)

Dave Wischnowsky Dave Wischnowsky
If nothing else, Dave Wischnowsky is an Illinois boy. Raised in...
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By Dave Wischnowsky –

(CBS) Starlin Castro is occasionally forgetful (remind me again how many outs are in an inning). He’s often sloppy in the field (12 errors in 67 games). And he’s always impatient at the plate (only six walks so far this season).

But this season, the Chicago Cubs’ precocious shortstop also has 16 steals, six triples and just went 3-for-5 with a two-run homer Monday night during the team’s 12-3 rout of the White Sox.

Oh, and the kid is on pace to tally his 500th career hit in August – at the age of 22.

So, while I certainly understand why some Cubs fans may want to trade Castro – he is a frustrating talent – the fact remains that he’s an enormous one, as well. And I think it would shortsighted for Theo Epstein & Co. to deal the kid this season, or at any other time in the near future, for that matter.

After all, there are big risks involved in bailing this early on a kid with this kind of ability. And if the Cubs were to part with Castro, they just might come to regret it, as the club certainly has done before.

When it comes to trades, let history be our warning as I present to you the five worst trades in Chicago baseball history.  Not surprisingly, four of them were made by the Cubs …

5. The Cubs trade Josh Hamilton

In the 2006 Rule 5 Draft, the Cubs selected Josh Hamilton – yes, that Josh Hamilton – only to immediately trade the troubled talent to the Cincinnati Reds for $100,000.

At the time of that transaction, Hamilton was only 25 years old. But he also was an enormous question mark, as the former No. 1 overall pick by Tampa Bay in 1999 was fresh off a series of rehab stints in his highly publicized battle against substance abuse.

There was no way of knowing that the ridiculously talented Hamilton, now absolutely destroying pitchers for the Rangers, would recover so ridiculously well. So, it’s hard to knock the Cubs too much for trading him so soon six years ago.

But Hamilton sure would have looked great on those good Cubs teams in 2007 and 2008, wouldn’t he?

4. The Cubs trade Dennis Eckersley

Speaking of substance abuse, alcoholism was a big reason why, in 1987, the Cubs traded a troubled Dennis Eckersley to the Oakland Athletics for three minor league prospects.

At 33 years old and with a dozen seasons under his belt, Eckersley was far from a fresh-faced prospect like Castro. But he was about to be re-invented. Once Eck headed west and got himself cleaned up, A’s manager Tony LaRussa transformed him from a solid starting pitcher into the best closer we’ve seen this side of Mariano Rivera and helped lead the A’s to the 1989 World Series title.

The Cubs, meanwhile, kept on searching for a closer of their own.

3. The Cubs trade Rafael Palmeiro and Jamie Moyer

Speaking of closers, in 1988, the Cubs targeted Texas Rangers closer Mitch Williams and swung a deal in which they got him by giving up 24-year-old outfielder Rafael Palmeiro and 26-year-old pitcher Jamie Moyer.

Williams, aka “Wild Thing,” went on to have a 36-save season for the Cubs’ NL East division winners in 1989, but he hardly had the staying power of Palmeiro, who belted 569 home runs and 3,020 hits before retiring in PED-tainted disgrace. Or Moyer, who has now won 269 games.

And is still pitching at age 49.

2. The White Sox trade Sammy Sosa

Not every lopsided baseball trade in Chicago belongs to the Cubs. The White Sox had a whopper of their own in 1992 – involving the Cubs – when they made the infamous decision to deal 23-year-old (or so) Sammy Sosa and pitcher Ken Patterson for 32-year-old slugger George Bell.

Bell went on to hit 38 home runs over the next two seasons for the Sox. Sosa, meanwhile, hit 545 homers for the Cubs during the next 13. He also defined baseball in Chicago for a decade before leaving town in 2004 with a corked bat, a smashed boom box and various steroid accusations in his controversial wake.

1. The Cubs trade Lou Brock

The granddaddy of all bad trades – not just in Chicago, but perhaps in the history of baseball – came in 1964 when the Cubs decided to part ways with a fleet-footed, 24-year-old outfielder for a sore-armed pitcher in the infamous “Brock-for-Broglio” deal.

Lou Brock first broke into the bigs at the age of 21, but the Cubs lost patience with his development after he batted a combined .260 over his first two seasons. So, in ’64, just before the June 15 trade deadline, they dealt him and two other players to the archrival Cardinals for starting pitcher Ernie Broglio, who had won 18 games the previous season.

In the deal, the Cubs also received starting pitcher Bobby Shantz and an outfield prospect, prompting many at the time to believe the trade was a heist for the Cubs. It wasn’t.

The sore-armed Broglio went 7-19 in three seasons for the Cubs. Brock, meanwhile, hit .348 and stole 38 bases during the remainder of the 1964 campaign and led St. Louis to the World Series championship over the New York Yankees.

He then went on to play 15 more years for the Cardinals, starring in two more World Series (1967 and ’68) before retiring with the all-time stolen bases record and a bust in Cooperstown.

So, for those wishing to trade a 22-year-old Castro, be very careful what you wish for.

davewisch Wisch: The 5 Worst Trades In Chicago Baseball History

Dave Wischnowsky

If nothing else, Dave Wischnowsky is an Illinois boy. Raised in Bourbonnais, educated at the University of Illinois and bred on sports in the Land of Lincoln, he now resides on Chicago’s North Side, just blocks from Wrigley Field. Formerly a reporter and blogger for the Chicago Tribune, Dave currently writes a syndicated column, The Wisch List, which you can check out via his blog at http://www.wischlist.com. Follow him on Twitter @wischlist and read more of his CBS Chicago blog entries here.