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The Worst Trade Of The Past 5 Years (Not That One)

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PITTSBURGH, PA -James McDonald #53 of the Pittsburgh Pirates pitches against the Cincinnati Reds during the game.  (Photo by Justin K. Aller/Getty Images)
PITTSBURGH, PA -James McDonald #53 of the Pittsburgh Pirates pitches against the Cincinnati Reds during the game. (Photo by Justin K. Aller/Getty Images)
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Earlier in the week, I made a distinction between trades that look bad in retrospect, and trades that were clearly awful at the time. Trading a vial of expired antibiotics for a bag of Funyuns would sure look bad after the Yellowstone caldera exploded and society collapsed. Trading a bottle of 30-year-old single malt for a bag of Funyuns is clearly awful at the time. Unless you're really, really hungry.

On July 26, 2008, the Los Angeles Dodgers were a game out of first place. They traded Carlos Santana for Casey Blake, and Blake helped them to the NLCS. In retrospect, the Dodgers would probably trade the NLDS victory and playoff appearance for Carlos Santana. It looked like a somewhat-fishy trade at the time, but considering that the Dodgers almost made it to the World Series … eh, you can see the argument for it. It looks much worse in retrospect. That doesn't make it an awful trade at the time.

On July 31, 2010, the Los Angeles Dodgers were five games out of the Wild Card race and seven games out of the NL West lead. They had lost four in a row and 11 of their last 16. They traded James McDonald for Octavio Dotel, who threw 18 innings for them over the next month-and-a-half before they shipped him to the Rockies in a September deal.

That might be -- and I'm not going through every one, so I could be wrong -- the worst trade I can remember.

Nolan Ryan for Jim Fregosi? If WAR existed back then, that would have been a widely lauded trade. Fregosi was an All-Star shortstop coming off a down year. Perfect buy-low candidate.

Christy Mathewson for Amos Rusie? Rusie was a two-time ERA leader, and Mathewson was an unproven teenager.

Vernon Wells for Mike Napoli? Uh ... uh ... well, you see ... hold on, someone's at the door.

You can make arguments for just about any trade. But "live-armed prospect", "middle reliever", and "five games out of the Wild Card (and behind three other teams)" combine to form a supergroup of bad trade ideas. The Damn Yankees or Alcatraz of bad trade ideas, even. Is it a good idea to trade a live-armed prospect? Depends. Is it a good idea to trade anything of value for a middle reliever? Probably not. Is it a good idea to trade for anything when you're five games out? Heck, no.

All three? Amazing.

This comes up because McDonald is pitching on Friday for the Pittsburgh Pirates. When bad teams have fire sales every summer, this is the trade they're hoping for: a spare part shipped out for an interesting prospect. And it looks like McDonald has successfully made the transition from "interesting prospect" to "valuable major-league piece."

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Provided by View Original Table Generated 5/10/2012.

The strikeout rate is above-average. The control is improving. It's a small sample, but he flashed promise last year, too. For years, the Pirates have been trying to trade their spare parts for players who could help them for the long-term. With McDonald, they might have one. And it's worth noting things might not be the same if McDonald stayed with the Dodgers, that he might not have developed in the same way. You know, if he didn't go to that pitching factory in Pittsburgh.


But that's not the point. None of that matters. Even if McDonald never threw a pitch for the Pirates, the trade still would have been an amazingly bad one. If all trades are a combination of risk vs. reward, what could Ned Colletti have possibly figured would be the reward? What could Dotel have done to help the Dodgers make up five games, and was it worth five or six seasons of James McDonald? Even if McDonald never becomes a star, per se, he could have saved the $12 million they're going to pay Aaron Harang. And then Frank McCourt could have used those savings to pay for the extended warranty on his robo-Bentley. Win/win.

Carlos Santana might be the better player right now. He will probably have the better career. He'll be the prospect who got away in a lot of eyes. But James McDonald was shipped off in the worse trade. Everything looks better or worse in hindsight. That trade was baffling from the second it was announced.

The point of this isn't to needle the Dodgers or their fans. They're in first place -- they don't care right now. The point is to write about how James McDonald is a pretty interesting pitcher right now, and what in the hell was that trade about?