10 Worst Trades in Baseball History

The Los Angeles Dodgers traded Pedro Martinez to the Montreal Expos in 1993 for second baseman Delino Shields. Shields spent three unproductive years with the Dodgers, while Martinez became one of baseball's best starting pitchers.

Martinez won 55 games and lost 33 in four seasons with the Expos, winning the first Cy Young Award (given to the best pitcher in each league) in 1997. He posted a diminutive 1.90 ERA (that's very good for you non-baseball fans) that year. In 1998, the cash-strapped Expos sent Martinez to Boston for Carl Pavano and Tony Armas Jr. By that time, the Expos could not afford to pay Martinez and would have lost him to free agency anyway [source: ESPN].

During his 18-year career, Martinez won two additional Cy Young Awards and 219 games, and posted a 2.93 ERA [source: Baseball Almanac]. DeShields didn't do as well. He played three seasons with the Dodgers, never hitting higher than .256 [source: Baseball Reference].

Why did the Dodgers trade Martinez? That question still has Dodger fans scratching their heads. Surgeons repaired the young right hander's left shoulder in 1992 after Martinez dislocated it swinging a bat. When Martinez came back the following year, he made 65 appearances for the Dodgers, posting a 10-5 record. He struck out 119 batters in 107 innings. Dodger management obviously thought the injury was too great to keep Martinez around [source: Newhan].

As the 1998 trading deadline loomed, the Seattle Mariners unloaded their pitching ace Randy Johnson, sending the lanky left hander to the Houston Astros. Johnson automatically made Houston the favorite to win the National League. The "Big Unit" went 10-1 with a microscopic 1.90 ERA and 116 strikeouts in 84.1 innings. As a result, the Astros topped the Central Division, ultimately losing to the San Diego Padres in the National League Division Series [source: Bleacher Report].

The Astros had given up several minor league prospects for Johnson, including pitchers Freddy Garcia, John Halama and shortstop Carlos Guillen. Although not the "worst" trade in history, Garcia, Halama and Guillen helped Seattle win 116 games in 2001. Garcia tallied an 18-5 record and emerged as the new Mariner ace [source: Bleacher Report].

On Dec. 9, 1965, the Cincinnati Reds traded Frank Robinson to the Baltimore Orioles for pitchers Milt Pappas, Jack Baldschun and outfielder Dick Simpson. Robinson made his professional debut with the Reds in 1956. Nine years later, Reds General Manager Bill DeWitt dealt Robinson believing the slugger too old. Robinson was 30. Pappas pitched for the Reds for two-and-half seasons, winning 30 games and losing 9. Baldschun and Simpson accomplished little with the Reds [source: History.com].

As for Robinson, he ultimately became a Hall of Famer. He won the Triple Crown in his first season with the Orioles. He hit the most home runs (49); batted in the most runs (122); and led the league with the best batting average (.316). Robinson also led the O's to its first World Series win over the Los Angeles Dodgers. Robinson spent six years with the Orioles, winning another World Series in 1970, this time over his former team, the Reds [source: History.com].

The Mets have made some bad decisions over the years, but nothing can top Dec. 10, 1971 when New York's other team dealt pitcher Nolan Ryan and three others to the California Angels in exchange for shortstop Jim Fregosi. In hindsight, it was one of the worst trades ever, but no one complained at the time. That's because the young Ryan was erratic at best. He posted a 29-38 record over five seasons with the Mets, walking 344 and striking out 493. In a sense, it was a no-brainer for the Mets to get rid of Ryan. They desperately needed someone to play third base [source: Sports Illustrated].

As it turned out, Ryan turned into one of the best pitchers in the game. He threw seven no-hitters during his career. In six out of his first seven seasons with the Angels, Ryan led the American League in strikeouts and walks [source: Sports Illustrated]. Fregosi lasted only 146 games with the Mets, batting just .233. He was sold to Texas in the middle of the 1973 season [source: ESPN].

Have you ever heard of Doyle Alexander? Probably not. Frankly, he wasn't a bad pitcher. The right hander knew how to throw strikes. In 1987, the Detroit Tigers were in the middle of a pennant race and needed another arm to close the deal. They traded a young prospect named John Smoltz for Alexander.

Drafted in the 22nd round in 1985, Smoltz was young and had a hefty 5.73 ERA in AA minor league ball. He walked more batters than he struck out. At the time, it was a good trade for Detroit. Alexander went 9-0 for the Tigers with a miniscule 1.53 ERA. He helped the Tigers win the American League Eastern Division, but they lost to the Minnesota Twins in the league championship game [source: Mensching].

Smoltz started out slow with the Braves. He won two of the 12 games he started in 1988. The next year, he had a 12-11 record. By 1996, Smoltz had a 24-8 record and eventually became a Hall of Fame pitcher. Among other accomplishments, Smoltz was an eight-time National League All Star, he won the 1996 Cy Young Award, he tallied 50 saves during the 2002 season and won the World Series with the Braves in 1995 [source: Baseball Reference].

Before Mark McGwire, Barry Bonds, Sammy Sosa and allegations of steroid use, there was Roger Maris, a chain-smoking outfielder who set baseball's single-season home run record in 1961. Maris, with his patented crew cut, accomplished the feat as a New York Yankee. Before he donned the pinstripes, Maris played for the Kansas City Athletics. The Athletics shuttled Maris to New York in exchange for legendary pitcher Don Larsen (he threw the only perfect game in World Series history), Norm Siebern and an aging Hank Bauer. The Yankees also got Joe DeMaestri and Kent Hadley in the trade [source: Knapel].

In 1961, Maris set baseball on fire. Teamed with Mickey Mantle, the "M & M Boys," as they were dubbed, chased after Babe Ruth's celebrated single-season home run mark of 60. Mantle and Maris battled each other until Mantle dropped out of the race early due to an injury. Maris tied Ruth's record on Sept. 26, and surpassed the Sultan of Swat on the final day of the season. He was voted the American League's Most Valuable Player [source: RogerMaris.com]. McGwire broke Maris's record in 1998, later admitting in 2010 that he used performance-enhancing drugs during the season.

When the Chicago Cubs traded Lou Brock to the St. Louis Cardinals for pitcher Ernie Broglio in 1964, it didn't seem like such a bad move. Broglio had won 21 games and lost only 9 in 1960. He was young and had many good years left in him, or so everyone thought. Brock, who had played for the Cubs for two-and-a-half years, didn't burn up Wrigley Field. His batting average with the Cubs in 1963 was a lowly .251, slightly worse than the .262 he batted the year before [source: Baseball Reference].

In his first game with the Cardinals, Brock struck out on three pitches. Then he caught fire. Brock hit .348 for the rest of the 1964 season and stole 33 bases. The Cards became champions of the National League that year. Brock found his stride with the Cardinals, hitting .300 seven times from 1965 to 1979. He led the league in stolen bases eight times, and retired as the all-time steals leader. Broglio, on the other hand, retired to the dust bin of history. He won only four games with the Cubs in '64, and left the game after 1966 [sources: Baseball Reference; Sports Illustrated].

Despite their success, the New York Yankees have made some questionable personnel transactions over the years. In 2003, they traded for pitcher Kevin Brown, a 39 year old, who had seen better days. In 2004, Brown won 10 games until he broke his hand punching a wall. Brown was supposed to be a big-game pitcher. He wasn't. In 1999, the Florida Marlins acquired Mike Lowell from the Yankees. Lowell was solid with the Marlins, and helped them beat the Yankees in the 2003 World Series. He also played for the Red Sox where he was the cornerstone of the team. The list goes on.

Yet, the worst trade of the storied franchise occurred in 1988 when the Bronx Bombers got rid of Jay Buhner. The Yankees sent Buhner and another player to the Seattle Mariners for Ken Phelps.

The teams consummated the trade on July 21, 1988. Buhner was young and just starting his career. Phelps was 33 years old, ancient by baseball standards. During the second half of the 1988 season, Phelps batted a laughable .244 with 10 homers. Buhner played 13 seasons with Seattle, hitting 310 career home runs [source: Rush].

Try to look past Mark McGwire's use of performance enhancing drugs. Try not to remember the Congressional stonewalling. Try to forget his self-imposed exile from baseball after allegations of steroid use tarnished his legendary career. In 1997, the Oakland A's traded McGwire to the St. Louis Cardinals for T.J. Matthews, Blake Stein and Eric Ludwick.

At the time, the San Francisco Chronicle said the trade might haunt the A's just as Babe Ruth's trade haunted the Red Sox (more on that later). The A's traded McGwire before the July 31 trading deadline. The first baseman was eligible to become a free agent at the end of the year [source: Blackman].

In his first full season with the Cardinals, McGwire broke Roger Maris's single-season home run record. Big Mac belted 70 homers. He helped restore fans' interest in baseball after a calamitous strike in 1994 nearly ruined the game. In 1999, McGwire hit 65 homers. Matthews, Stein and Ludwick didn't amount to much [source: Fogelgaren].

Jan. 5, 1920. Harry Frazee held a press conference to announce that the Red Sox had sold Babe Ruth for cash to the New York Yankees. "The price was something enormous," Frazee said, refusing to name the figure. "It was an amount the club could not afford to refuse" [source: Shaughnessy].

"Prohibition was 11 days away when Frazee made this move, which would drive Sox fans to drink," sportswriter Dan Shaughnessy wrote 70 years later in "The Curse of the Bambino." "Ruth became the foundation for the greatest dynasty in the history of professional sports" [source: Shaughnessy].

No matter how you slice it, no matter how many arguments you get in, the worst trade in baseball history, nay, the worst trade in sports history occurred on that cold January day in 1920. It's not as if the Red Sox did not know what they had in Ruth. For six years, Ruth tallied some remarkable numbers. He was a stellar pitcher, winning 18 games in 1915; 23 a year later; and 24 in 1917. He batted above .300 in four of those six years [source: Baseball Reference].

Yet, it was with the Yankees that Ruth would achieve his iconic status. He became a full-time outfielder, leading the Yankees to four World Series victories and becoming baseball's home-run king. He hit 60 homers in 1927 and 714 during his career. Ruth was larger than life. He was famous on and off the field, a superstar before there were superstars, a cultural icon before there were cultural icons. His talent on the field saved baseball after the 1919 Black Sox scandal threatened to ruin the game.

As for the Red Sox, the "Curse of the Bambino" lingered for more than 80 years. Finally, in 2004 the Sox won their first World Series since 1918. They won again in 2007, perhaps exorcising The Curse of the Bambino forever.

Or, perchance, they're just teasing their fans.