Why it's a bad idea to name your son Delino

I just read an Associated Press story that quoted the ex-wife of Delino DeShields, a former outfielder and lead-off man from 1990-2001. After reading the story, I went on Wikipedia, as I often am apt to do, and checked out DeShields’ page. On it, I saw something I didn’t know: DeShields once got traded from the Montreal Expos to the Los Angeles Dodgers for a young Pedro Martinez. The Wikipedia story said that it’s generally considered one of the worst trades of the Dodgers’ 50-year history in Los Angeles, which made sense, though that’s not to say it worked out that much worse as a trade than Ebbets Field for Chavez Ravine.

This all got me thinking about some of the other worst trades in baseball history. My friend Devin and I used to have this joke when we were growing up. As young San Francisco Giants fans, we for some reason hated the Houston Astros and their manager at the time, Art Howe. We used to pretend to call up Howe, get him to trade his entire team for Giants’ center fielder Brett Butler and then say, “Ha, ha, fooled ya!” Most general managers are not this stupid. However, I think Devin and I may have been able to put one over on a few guys. Witness their handiwork. The following are some of the worst trades that have ever been made in baseball history, listed in no particular order:

1) DeShields for Martinez: This is one time the hapless Expos got it right, unloading the mercurial DeShields for Martinez, who went on to win three Cy Young awards, including his first with Montreal in 1997.

2) Bartolo Colon for Cliff Lee, Grady Sizemore and Brandon Phillips: One of the many times the Expos got it gloriously wrong. Give them credit for being aggressive. In the midst of a rare pennant race, they traded for Cleveland Indians ace Colon, who was in the middle of a 20-win season. However, the Expos failed to make the post season and gave up three All-Star caliber players in the process. Done over, Colon for even one of these guys is probably still uneven.

3) Babe Ruth for “No, No, Nanette”: The Sultan of Swat was sold to the New York Yankees in the winter of 1920 so that Boston Red Sox owner Harry Frazee could finance a Broadway musical, “No, No, Nanette.” It was a hit, but Boston failed to win the World Series for another 84 years.

4) Nolan Ryan for Jim Fregosi: To be fair, no one had seen what Ryan could do when the New York Mets dealt him to the California Angels. And there’s a part of me that says Ryan was little more than a slightly above-average pitcher who simply had phenomenal longevity. Still, there’s really no justifying this deal.

5) Mark McGwire for TJ Matthews, Blake Ludwick and some other shitty player I can’t remember. I could go check Baseball Reference but it isn’t worth the time.

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