Monday, March 29, 2010

7 of the Worst Trades in Baseball History

The negotiations for trading players between major league ballclubs can be tense, drawn-out matters, because you just never know what you're actually going to get or give away (especially when it comes to prospects) until the deal is done. With 7 days remaining until Opening Day, here are my picks for 7 trades that I'll bet each club would love to have been able to take back:

#7: 12/9/82 Philadelphia Phillies trade FIVE players to Cleveland Indians to get Von Hayes

During his unremarkable stint in Philadelphia, Von Hayes was known as "Old 5-for-1" thanks to this deal. One of the baseball trivia questions is: Can you name the five players the Phillies dealt away for Hayes? Answer: Manny Trillo, Julio Franco, George Vuckovich, Jay Baller and Jerry Willard. The biggest names there, Trillo and Franco, were at the end and beginning of their careers respectively, and Hayes was a hot commodity at the time, but five players for one?

#6: 1/27/82 Philadelphia Phillies trade Larry Bowa and Ryne Sandberg to Chicago Cubs for Ivan DeJesus
Yeah, a month later, the Phils made an ever more lunkheaded trade, again sending away a supposedly aging veteran and an untested rookie to get a fair-to-middling player. In this case, Bowa put in some decent years with Chicago and Ryne Sandberg went on to have a Hall-of-Fame career. Ivan DeJesus? Not so much...

#5: 12/10/82 San Diego Padres trade Ozzie Smith to St. Louis Cardinals for Gary Templeton
Whatever was affecting the minds of the Phillie's brass when it came to trading in the winter of '82 was also in the air in San Diego. Smith was still early in his career, but his abilities certainly were not a question. Gary Templeton was a decent shortstop, but nowhere near The Wizard's level. What were they thinking?

#4: 7/31/97 Oakland A's trade Mark McGwire to St. Louis Cardinals for TJ Matthews, Blake Stein and Eric Ludwick

Fifteen years later the Cardinals were still stealing bargains from California-based teams, this time picking up one of the game's most noted (and most controversial) sluggers for the equivalent of a handful of magic beans.

#3 8/30/90 Boston Red Sox trade Jeff Bagwell to Houston Astros for Larry Andersen
Ah yes, the classic prospect-for-veteran trade. The Astros were looking for late-season pitching help, and figured, hey, it's only going to cost us one prospect. Bagwell turned out to be one helluva prospect, and Andersen still chuckles about being involved in this trade.

#2 12/9/65 Cincinnati Reds trade Frank Robinson to Baltimore Orioles for Milt Pappas, Jack Baldschun and Dick Simpson
The Reds figured that at age 30, former NL MVP Frank Robinson's best years were behind him, but that he'd be enough of a name on trading market to bring them a few good prospects. Pappas was probably the best of the three they picked up, and he wasn't that good. Old Man Robinson? Oh, he just went on that year to win the Triple Crown and AL MVP honors for Baltimore...

#1 12/10/71 New York Mets trade four players for Jim Fregosi
One shy of matching the Von Hayes 5-for-1 deal in numbers, this may have been the worst trade ever. Fregosi would be much more successful as a manager than as a ballplayer, although he was no slouch on the field. Three of the four players the Mets traded (Don Rose, Leroy Stanton and Francisco Estrada) didn't accomplish a whole heckuva lot. But the fourth player they traded away in the deal? Some hard-throwing pitcher the Mets didn't feel had the control to be successful. He went on to prove them very, very wrong. His name was Nolan Ryan.

Any head-scratchers I missed? Share your favorite terrible trades in the comments section below!


  1. Tigers trade Doyle Anderson for John Smoltz

  2. Just thinking about the S.F. Giants, I would put Francisco Liriano, Joe Nathan, and Boof Bonser for A.J. Pierzynski right up there.

    Also, in order of badness from there...

    - George Foster for Frank Duffy
    - Gaylord Perry for Sudden Sam McDowell
    - Orlando Cepeda for Ray Sadecki