C.C., Bedard, Colon
The Sabathia trade seems like a clear example of a trade that helps both teams. Despite preseason expectations, the Indians are clearly out of the race; they no longer need Sabathia. The Brewers are in a tight race (they're currently tied for the Wild Card). Sabathia makes them the clear favorite to win the Wild Card and helps their chances in the postseason. Matt LaPorta is a great offensive prospect who could be a star in Cleveland, but was probably a poor fit on a team that already has a young star at first base; a young star who is defensively challenged in left field; and a very good right fielder who might be stretched defensively in center.
Next up on the trading block: Erik Bedard? The Mariners are out of the race and don't seem to pleased with Bedard, but they have a problem: it'll be embarrassing when they don't get nearly as much in return as they gave up to get him five months ago. The Mariners never should've traded Adam Jones (and Sherrill, etc.) for Bedard; their team simply wasn't good enough to compete this year.
The Bedard situation sort of reminds me of another portly Cleveland pitcher: Bartolo Colon. On June 27, 2002, the Expos traded Grady Sizemore, Cliff Lee, and Brandon Phillips for Colon. The following January, they traded Colon and only received Orlando Hernandez, Rocky Biddle, and Jeff Liefer in return. Omar Minaya's excuse for dumping so much talent in the first place is that he thought the Expos wouldn't be in existence for long, so there was no need to hold onto the prospects. That always sounded a little dubious to me - there was clearly at least a chance that the Expos would be sold and moved to another city and that a strong farm system should've (at least in theory) resulted in a higher price for the franchise.
Another flaw in Omar's theory is that the Expos didn't really have a good shot at making the playoffs with or without Colon. They were 6.5 games behind the Braves in the East and they were 5 games behind the Diamondbacks in the Wild Card race. The Expos were also 2 games behind the Giants and tied with the Reds. The Expos had given up more runs than they had scored, so their 41-36 record was probably somewhat of a fluke. Not surprisingly, they went 42-43 the rest of the way, finishing 19 games behind the Braves and 12.5 behind the Giants for the Wild Card. Colon pitched as well as could have been expected, but the team just wasn't playoff material.
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I think Omar must've thought he was not going to be retained as GM once the team was sold. While making such a rash trade like that could've hurt his reputation, why not go out guns blazing? And to top off his screwing over of the Expos/Nats, the Church-Schneider/Milledge trade still looks one-sided, and will do so until Milledge can hit a slider.
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