As the July 31 MLB trade deadline approaches, let’s look at some of the dumbest trades in baseball history.
My picks aren’t presented in any particular order, although the Babe Ruth trade has to be first on any list. It’s hard to grade stupidity. On the other hand, hindsight is always 20/20.
Babe Ruth for a mortgage on Fenway and $125,000 cash. The Babe had led the Boston Red Sox to three world championships in five-plus years when, in 1919, owner Harry Frazee sold him to the New York Yankees for $125,000 and a $300,000 loan to produce a Broadway show. The following year, Ruth hit 54 home runs; the Sox hit 22 as a team. The Babe would lead the Yanks to four championships and seven pennants. Boston would not win another World Series until 2004.

Ryan as an Angel (photo courtesy MLB.com)
Nolan Ryan for Jim Fregosi: On December 10, 1971, the New York Mets dealt Nolan Ryan and three others to the then-California Angels for former All-Star shortstop Jim Fregosi. The Mets were in desperate need of a third baseman, and the young Ryan was erratic. He posted a 29-38 record over five seasons with the Mets, walking 344 and striking out 493. Fregosi lasted less than two seasons, batting just .233 before being shipped off to Texas. Ryan turned into one of the best pitchers in the game. The Hall of Famer threw seven no-hitters.
Lou Brock for Ernie Broglio: When the Chicago Cubs traded Lou Brock to the St. Louis Cardinals for pitcher Ernie Broglio in 1964, it seemed like a smart move by the Cubbies. Broglio went 21-9 in 1960. Brock had batted .251 in 1963, slightly worse than the .262 he batted in 1962. But after the trade, Brock batted .348 the rest of the year and helped the Cards win three pennants and two World Series over the next 15 seasons, stealing 938 bases on his way to the Hall of Fame. Broglio played a little more than two seasons with the Cubs, compiling a 7-19 record before retiring.

Hall of Famer Frank Robinson was the only player to win the MVP award in both major leagues. He was also baseball’s first black manager (photo, NPR)
Frank Robinson for Milt Pappas: On December 9, 1965, the Cincinnati Reds traded Frank Robinson to the Baltimore Orioles for pitchers Milt Pappas, Jack Baldschun, and outfielder Dick Simpson. Reds General Manager Bill DeWitt thought Robinson was “an old 30.” In his first year with the Orioles, the Hall of Famer won the American League Triple Crown, led his team to a World Series championship, and was named MVP. Pappas went 30-29 over the next two-plus seasons before being shipped off to Atlanta. Baldschun and Simpson accomplished little with the Reds.
Joe Nathan and Francisco Liriano for A.J. Pierzynski: The Giants thought catcher A.J. Pierzynski was the missing piece to a playoff run in 2004. They sent Joe Nathan, Francisco Liriano, and Boof Bonser to the Twins. Nathan became one of the best closers in the game, and Liriano had some great seasons in Minnesota. Bonser was a serviceable arm for the Twins for a short time. Pierzynski was best known for being a cancer in the Giants’ clubhouse and for grounding into double plays. He was dealt to the White Sox the next season, and strangely enough, Chicago won the World Series with Pierzynski as the backstop.
Pedro Martinez for Delino DeShields: The Los Angeles Dodgers traded Pedro Martinez to the Montreal Expos in 1993 for second baseman Delino DeShields. 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 of his three Cy Young Awards in 1997. In 1998, the cash-strapped Expos sent Martinez to Boston for Carl Pavano and Tony Armas Jr. The Expos could not afford Martinez and would have lost him to free agency anyway.

Here it comes! (photo courtesy Seattle Times)
Expos trade Randy Johnson to Mariners: In 1989, the Expos dealt Johnson, Brian Holman, and Gene Harris for Mark Langston and Mike Campbell. Langston was a solid pitcher, but the Big Unit went on to win five Cy Young Awards, make 10 All-Star appearances, win more than 300 games, win a World Series, pitch a perfect game, and rank second all-time in strikeouts.
George Foster for Frank Duffy and Vern Geishert: On May 29, 1971, the Cincinnati Reds traded shortstop Duffy along with pitcher Geishert to the Giants for Foster. Geishert, who had played briefly in the majors in 1969, never played in the majors again. Duffy played just 21 games for the Giants before being dealt to the Cleveland Indians. Foster became an essential cog in the Big Red Machine. He tore up the league with the Reds through 1981 and added four more respectable seasons with the Mets until retiring after the 1986 season.
Dennis Eckersley for three minor leaguers: On April 3, 1987, the Cubs, who considered starter “Eck” washed up, dealt him to the Athletics for three prospects who never reached the majors. Converted to a closer by the A’s, Eckersley became one of the greatest relievers in baseball history. He saved 387 games over the next 12 seasons, winning the Cy Young Award and MVP in 1992. In 2004, Eckersley was inducted into the Hall of Fame.
Mets trade Tom Seaver to the Reds: The Mets would not pay Seaver what he thought he was worth, and just before the trade deadline, decided to deal him to the Reds for minor league outfielders Steve Henderson and Dan Norman, pitcher Pat Zachry, and utility infielder Doug Flynn. None of the players made a significant impact for the Mets, and the Reds acquired one of the best pitchers in Major League Baseball history. The deal became known as “The Midnight Massacre.”
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This article originally appeared in the Vallejo Times-Herald on April 18, 2020.













