The 5 Best and Worst Trades in MLB History

Because not everyone gets a sweet deal

Because not everyone gets a sweet deal

(left to right:Ryne Sandberg, Larry Bowa, Ivan DeJesus)


1. Ryne Sandberg and Larry Bowa traded by the Philadelphia Phillies to the Chicago Cubs for Ivan DeJesus in 1982.

Two years after leading the Phillies to their first World Series championship in its pathetic 97-year history, manager Dallas Green left to become GM of the Cubs. His first significant move was a deal that was positively Madoff-ian but legal: He traded for a future all-time great (Ryne Sandberg) by giving up a mediocre shortstop (DeJesus). Cold blooded.

2. Derek Lowe and Jason Varitek traded by the Mariners to the Boston Red Sox for Heathcliff Slocumb in 1997

The battery helped the Sox end the curse in 2004, and it enabled Sox fans to stop muttering “Bucky Fucking Dent” (the marginal Dent hit the decisive home run in a one-game playoff in 1978 after the Sox blew a 15-game regular season lead to the Yankees) every time the Yankees made the playoffs.

3. David Cone traded by the Toronto Bluejays to the New York Yankees for Marty Janzen, Jason Jarvis and Mike Gordon in 1995.

Cone was traded for three guys who never made the majors, and he went on to start the last Yankees dynasty by winning 55 games. He also pitched a perfect game and was adored by his large Yankee fan base, known as ‘Coneheads.’

4. The Mets trade Harry Chiti to the Cleveland Indians for Harry Chiti in 1962.

General managers sometimes note how some deals are of equal value. Well, it’s hard to be more equitable than this trade. Chiti, who barely earned a footnote in baseball history, was dealt for a player to be named later, as himself.

5. Fritz Peterson and Mike Kekich trade their entire families, including dogs and cars in 1972.

Peterson and Kekich were a pair of forgettable journeyman pitchers, who rarely made news on the field. However, they caused a stir with their personal personnel moves when they were Yankees. “We didn’t trade wives, we traded lives,” Kekich said about the transaction. The deal wasn’t a MLB blockbuster but it might be a blockbuster film: Ben and Casey Affleck are writing a script dubbed ‘The Trade’ based on the swap.

(above: Babe Ruth)


1. The Boston Red Sox trade George Herman Ruth to the Yankees for $125,000 in 1920.

Whoever wrote that money can’t buy happiness was inspired by this nightmarish deal ,which enabled the Yankees to become the most enviable franchise in sports while the Red Sox embarked on the 86-year old ‘Curse of the Bambino.’

2. Nolan Ryan traded by the Mets to the Angels for Jim Fregosi in 1971.

The Mets gave up a young but wild talent, who became the greatest strikeout pitcher in history. Ryan threw more no-hitters (seven) than anyone on the way to a Hall of Fame career. Fregosi, who the Mets thought they stole, was in the twilight of a good career. Bernie Madoff might have ruined the current edition of the Mets, but the Ponzi schemer had nothing to do with this regrettable deal .

3. The Yankees trade Jay Buhner to Seattle for Ken Phelps in 1988.

The young, excitable Buhner became a power-hitting sensation for the Mariners, while the aging, fading Phelps was dealt away the following year. The deal was worth it if only for inspiring one of the all-time best Seinfeld lines, as Frank Costanza barked at George Steinbrenner, “What the hell did you trade Jay Buhner for??” 

4. The Cubs trade Lou Brock to the Cardinals for Ernie Broglio in 1964.

Forget about the “Curse of the Billy Goat” (the Cubs wouldn’t let one odd fan enter Wrigley Field with his goat during the 1945 series, so he put a hex on the team, which apparently still stands): Perhaps the darkest day of the Cubbies’ sad history is when they gave away a future Hall of Famer (Brock) to their arch-rival Cards for a solid pitcher, who suffered arm trouble and only won seven games for the North-siders.

5. The Boston Red Sox trade Jeff Bagwell to the Houston Astros for Larry Anderson in 1990.

The Sawx unload a blue-chip prospect, who goes on to win the 1994 NL MVP award and is probably headed for the Hall of Fame (Bagwell) for an aging relief pitcher, who had a decent slider and a great sense of humor. “I’m probably the only person who thought it was a good deal,” Anderson said.