Worst Baseball Trades Ever

I'd like to throw in the Brewers sending Richie Sexson to the Diamondbacks for Lyle Overbay, Chris Capuano, Chad Moeller, Jorge de la Rosa, and Craig Counsell. Now many of you may not care because it doesn't involve the Red Sox or any New York team, but look at the numbers: Sexson plays one season in Arizona, in which he sat out all but 23 games with an injury, while Overbay hits .301 with a franchise record 53 doubles in 2004 and follows with a respectable .276 year in 2005 (lifting his stock so high the Brewers get Dave Bush, Gabe Gross and Zach Jackson in return from the Blue Jays following the 2005 season), Capuano sits out 2004 but returns in 2005 to with 18 games, the most of any Brewer pitcher since Teddy Higuera in the 80s. Those two guys alone make this trade bad, but the Brewers got FOUR more guys (I only listed three because I forgot the last guy) aside from them.

"How you can trade Ken Phelps! He has an arm like a cannon!"

Smoltz for Alexander wasn't so bad at the time. The Tigers won the Series that year, no?

Alexander went 20-29 in his two year stint with the Tigers. I think keeping Smoltz would have been best.

Curt Schilling has been in a number of bad trades. The one that brought him back to the Red Sox was a steal also. Casey Fossum, Brandon Lyon, Jorge de la Rosa, and Michael Gross for Schilling. The Red Sox got a World Series out of that deal. The Diamondbacks? They got about a dozen saves out of Lyon.

Obligatory comment: Mets trade Kazmir for Zambrano

The Smoltz for Alexander made sense at the time. Without Alexander, it's very unlikely the Tigers would have made the playoffs that season.

Giants trade Francisco Liriano, Joe Nathan, and Boof Bonser for A.J. Pierzynski has got to be up there. And who can forget Ftrank Robinson for Milt Pappas?

How could anybody forget the Mariners trading Jason Veritek and Derek Lowe to the Red Sox for Heathcliff Slocumb.

Giants have a long, horrible history of bad trades. They been on the end of a few good ones too. I'll start with the good ones: Pirates trade Jason Schmidt and John Vander Wal to the Giants for Armando Rios and Ryan Vogelsong.

Marlins trade Rob Nenn to the Giants for Joe Fontenot, Mike Pageler, and Mike Villano.

Marlins trade Livan Hernandez to the Giants for Jason Grilli and Nate Bump

Hmm, probably shouldn't have included the Livan one, sorry. OK, on with the bad ones: Giants trade Orlando Cepeda to the Cardinals for Ray Sadecki.

Giants trade Gaylord Perry AND Frank Duffy to the Indians for "Sudden" Sam McDowell (as in suddenly useless).

Giants trade George Foster to the Reds for Frank Duffy and Vern Geishert.

Giants trade Jack Clark to the Cardinals for David Green, Gary Rajsich, Dave LaPoint, and Jose Uribe.

Oh, and how about the worst trade in the history of baseball: Yankees purchase Babe Ruth from the Boston Red Sox (I think it was for $100,000; helped the owner of the Bosox fund some Broadway musical or something).

Another that comes to mind: Phillies trade Ryne Sandberg and Larry Bowa to the Cubs for Ivan DeJesus.

Cubbies trade Dennis Eckersley with Dan Rohn to the A's for Brian Guinn, Dave Wilder, and Mark Leonette.

Oops, sorry, that last one was already mentioned. Padres trade Ozzie Smith, Steve Mura, and Al Olmsted to the Cardinals for Sixto Lezcano, Garry Templeton, and Luis DeLeon. Not as lopsized but the Pads trade away a HOFer.

Mets trade Nolan Ryan, Frank Estrada, Don Rose, and Leroy Stanton to the Angels for Jim Fregosi.

Cardinals trade Steve Carlton to the Phillies for Rick Wise (who was not too bad himself, I think he had a 2-homer game but still).

Wow, the Reds just stole players to build their Big Red Machine: Houston Astros trade Joe Morgan, Cesar Geronimo, Jack Billingham, Denis Menke, and Ed Armbrister to the Reds for Lee May, Tommy Helms, and Jimmy Stewart (It was a Wonderful Life).

A's trade Jimmy Foxx and Johnny Marcum to the Red Sox for Gordon Rhodes, George Savino, and $150,000.

I can't believe this one hasn't been mentioned yet, it changed the course of baseball history: The Red Sox trade Babe Ruth to the New York Yankees in 1919 in exchange for cash so that the Red Sox owner at the time could fund his play "No, No Nanette".

"The sun will rise, the sun will set, and I'll eat lunch." –Boston Red Sox GM Lou Gorman on trading Red Sox prospect Jeff Bagwell to the Houston Astros organization, 1989 or thereabouts

The Expos trade Pedro Martinez to Boston for Carl Pavano and Tony Armas, Jr.

Chicago Cubs trade Sammy Sosa and cash to the Baltimore Orioles for Jerry Hairston, Mike Fontenot, and Dave Crouthers. It wasn't bad because the Cubs got a steal in the mediocore Hairston or two minor leaguers. It was just that Sosa was SO BAD. Epically bad.....

I can't believe I forgot the Babe Ruth trade.

you can always edit! :)

Ben forgot about Babe Ruth. To be fair, so did the Red Sox! Having traded their best pitcher all those years ago, and spend that time in the wilderness, why would you then do exactly the same thing once you've recovered, and trade Pedro Martinez?

Alex....when did the Red Sox trade Martinez? And how does that relate to Babe Ruth????

Some of these are Mariner Trades. That's cool.

Let's not forget the Reds trading Paul O'Neil to the Yankees for

Roberto Kelly before the 1993 season.O'Neil went on to be one of

the best hitters in the AL in the 90's and the leader of their comeback championship teams.Kelly was traded by the Reds in mid-'94 and was with a different team every year until his career was over.