Boston Red Sox: The 10 Worst Trades in Franchise History
Boston Red Sox baseball is a mere five days away, but before the season starts, it'll be good for Red Sox fans everywhere to catch up on their history.
The Red Sox have a lengthy past, as they were part of the American League's eight original teams in 1901. With that long history comes a very detailed record of trades and transactions.
I've been tasked to present 10 of the most maligned deals, and here they are.
As a collective body, it's good for Red Sox fans to revisit the bad teams that dogged the franchise for decades. It keeps us grounded in the team's most fruitful era since the early 1900's.
Dan is a Boston Red Sox featured columnist. Follow him on twitter @dantheman_06.
10) Dave Henderson Trade
September 1, 1987: Traded to the San Francisco Giants for a player to be named later (Randy Kutcher).
Henderson’s home run in Game 5 of the 1986 ALCS was one of the most memorable plays in Red Sox history. However, during the ’87 season, a struggling Henderson was shipped out of town.
After playing just 15 games for the Giants, Henderson signed with the Oakland A’s the following offseason. During the next four years (1988-91), Henderson hit his stride, batting .275 and averaging over 20 HR and 80 RBI per year. During this stretch, he was a one-time All-Star, finishing 13th (1988) and 21st (1991) in MVP voting.
Henderson was a key component of the Athletics teams that made the World Series in three straight seasons (1988-90), bouncing the Red Sox from the playoffs twice (1988, 1990). Henderson even batted an astonishing .375/.412/.625 against his former club in the ’88 ALCS.
Kutcher never amounted to anything, batting just .224 in 277 plate appearances from 1988-90.
9) Fred Lynn Dealt to California
January 23, 1981: Traded With Steve Renko to the California Angels for Jim Dorsey, Joe Rudi and Frank Tanana.
The Red Sox had been in a tailspin ever since losing to the Big Red Machine in the 1975 World Series. So, prior to the ’81 season, they decided to shake things up and do the unthinkable: They sent Fred Lynn, a key component of the most dominant outfield in baseball at the time (along with Jim Rice and Dwight Evans), to the California Angels.
At the time, free agency was relatively new, and Lynn had just one option year remaining on his contract. Lynn, Carlton Fisk and Rick Burleson were pressing for arbitration in their free agency cases, and instead of seeing these through, the Red Sox dealt both Lynn and Burleson in separate deals and let Fisk walk.
Lynn went on to four productive seasons with the Angels from 1981-84. He was a three-time All-Star (1981-83) during this span. After that, he went on to Baltimore, where he maintained productive play for another three-and-a-half seasons. He eventually retired in 1990.
Dorsey appeared in just four games (8.0 IP) for the Red Sox, Rudi batted .180 in 49 games and retired following the ’82 season and Tanana made 23 starts for the Sox in ’81, going 4-10 with a 4.01 ERA and 1.31 WHIP.
8) Jim Lonborg and Others to Milwaukee
October 10, 1971: Traded with Ken Brett, Billy Conigliaro, Joe Lahoud, Don Pavletich and George Scott to the Milwaukee Brewers for Pat Skrable, Tommy Harper, Lew Krausse and Marty Pattin.
A former Cy Young award winner and hero of the 1967 dream team, Lonborg went on to have a productive career with the Brewers and Phillies from 1972-79. During this period, he was 89-72 with a 3.79 ERA and 1.31 WHIP.
George Scott also went on to lead the league in HR (36) and RBI (109) in 1975 as a member of the Brewers, and after departing from Boston, he was consistently one of the game's better power hitters. Brett went on to become a middling, albeit usable reliever/starter, appearing in 270 games for eight teams across 10 seasons (1972-81).
Harper batted .259 and stole 107 bases for the Red Sox from 1972-74. Pattin had a decent two-year stretch with the Red Sox (1972-73), going a combined 32-28 with a 3.73 and 1.28 WHIP before a trade sent him to Kansas City, where he finished his career. Skrable and Krausse never did anything of significance.
7) Freddy Sanchez for Jeff Suppan
Craig Jones/Getty Images
July 31, 2003: Traded with Mike Gonzalez and cash to the Pittsburgh Pirates for Brandon Lyon, Anastacio Martinez, and Jeff Suppan.
It took a while for the Red Sox to feel the full force of this trade, but it still remains a blunder.
In an attempt to shore up their rotation for the postseason, the Sox brought in veteran pitcher Jeff Suppan at the deadline in 2003. Suppan proceeded to pitch atrociously, posting a 5.57 ERA and 1.43 WHIP in 10 starts. He was left off the postseason roster entirely, and that was that.
Sanchez, since becoming a full-time starter in 2005, is a career .300 hitter, a three-time All-Star (2006-07, 2009) and an NL batting champion (2006). He was a key part of the Giants team that won the World Series in 2010.
While Sanchez isn’t the flashiest or most productive player in the world, his services would have been perfect for the shortstop position, which has been in flux ever since Nomar Garciaparra left town in 2004.
Gonzalez has been a reliable reliever ever since the trade, and should be an integral part of the Baltimore Orioles ‘pen this year if healthy. Lyon gave the Sox 59.0 innings of mediocre relief in 2003 and Martinez has pitched in just 11 career games, all with the Red Sox in 2004.
6) Jamie Moyer for Darren Bragg
July 30, 1996: Traded to the Seattle Mariners for Darren Bragg
Moyer, who is still active at 47, pitched another 15 seasons in the big leagues after this trade, starting another 441 games. He survived on his guile, control and pitching smarts, and was able to capture a World Series title with the Phillies in 2008.
Bragg had a generally unimpressive career with the Sox, batting just .264 over three seasons (1996-98). Despite the fact that Moyer is nearly seven years older than Bragg, he outlasted him, playing six more big league seasons and producing at a much higher level.
However, the Red Sox got the M’s back the following season, as they fleeced Jason Varitek and Derek Lowe for Heathcliff Slocumb.
5) Curt Schilling and Brady Anderson for Mike Boddicker
July 29, 1988: With Brady Anderson to the Baltimore Orioles for Mike Boddicker
This is a hard trade to evaluate, because the Red Sox actually got the better of it for the short term.
To finish the 1988 season, Boddicker went 7-3 with a 2.63 ERA and 1.25 WHIP. He went a combined 32-19 with a 3.66 ERA and 1.32 WHIP over the next two seasons for the Sox, starting 34 games each year. He gave the Sox exactly what they were looking for: a veteran, established pitcher with postseason experience.
It took a while for this trade to be considered negative for the Sox, as Anderson and Schilling were late bloomers. Even after Anderson’s anomalous 50 HR campaign in ’96, he consistently hit for more power over his next four seasons. Schilling seemingly got better as he aged, going through a lengthy eight-and-a-half seasons with the Phillies before establishing himself as a legit ace in Arizona in the early 2000’s.
The Sox might have gotten exactly what they were looking for in the trade, but all transactions are viewed anachronistically. They gave up much more than what they got.
4) Sparky Lyle for Danny Cater
March 22, 1972: Traded to the New York Yankees for Danny Cater and a player to be named later (Mario Guerrero).
First baseman Danny Cater was 32 at the time of the trade. From 1972-74, he played in just 211 games, batting a measly .262/.301/.384. He played 22 games for the Cardinals in 1975 and then retired.
Lyle, however, was just 26 at the time of the deal. During the 1972 season, he saved 35 games for the Yankees, the most in the American League.
He went on to save 141 games for the Yankees from 1972-78. During that stretch he was a three-time All-Star (1973, 1976-77), a two-time World Series champion (1977-78) and a Cy Young award winner (1977), just the second reliever in MLB history to win the award.
Lyle helped to establish the tradition of dominant Yankee closers. Pitchers like Goose Gossage and Mariano Rivera, perennial tormentors of the Red Sox, are the spiritual descendants of Lyle.
3) Jeff Bagwell for Larry Anderson
August 30, 1990: Traded to the Houston Astros for Larry Anderson
During the stretch run of the 1990 season, the Red Sox felt the need to acquire some added bullpen depth. So, they went out and got Larry Anderson, a 37-year-old reliever in the midst of his 13th season in the bigs.
Anderson gave the Red Sox 15 games and 22.0 innings of solid relief, registering one save and posting a 1.23 ERA and a 0.96 WHIP.
And, that was it. The Red Sox were swept by the Oakland A’s in the ALCS, and Anderson moved on to the Padres and then the Phillies, playing four more years before hanging up the spikes for good.
Jeff Bagwell went on to become one of the greatest Houston Astros of all time, the owner of a career .297/.408/.540 slash line, 449 HR and 1,529 RBI. And that’s without mentioning his four All-Star selections, three Silver Sluggers, Gold Glove, Rookie of the Year award and MVP.
Bagwell played all 2,150 games and 15 years of his illustrious and borderline Hall of Fame career with the Houston Astros. All for 22.0 innings of bang-up relief.
2) Tris Speaker Sent to Cleveland
April 12, 1916: Traded to the Cleveland Indians for "Sad" Sam Jones, Fred Thomas and $55,000.
After refusing to take a pay cut following the 1915 season, Speaker was dealt to the Indians. At the time, Speaker and Ty Cobb were considered the best outfielders in the game.
At that point in his career, Speaker was a .337 hitter and a one-time MVP (1912), routinely swiping anywhere from 30-50 bases per year and finishing near the tops of the league in doubles. He also happened to be one of the best defensive players in the game.
Speaker finished his career with a .345/.428/.500 slash line, pretty good for a guy with only 117 HR in 28 seasons of play. Speaker is fourth all time in career batting average (.345), fifth in hits (3,514) and first in doubles (792). He was elected into the Baseball Hall of Fame in 1937, just the second class ever.
Jones went on to pitch six seasons for the Sox from 1916-21. After appearing in just 20 games of relief and making one start from 1916-17, he became a full-time starter in 1918. He finished with a career 64-59 record, along with a 3.39 ERA and 1.35 WHIP in Boston. Thomas played in just 44 games for the Sox in 1918, batting .257.
1) George Herman "Babe" Ruth Sold to the New York Yankees
January 3, 1920: Purchased by the New York Yankees for $100,000.
I mean, what else could really be here?
It doesn’t matter if you believe in the “curse” or not. The Red Sox, under the misguided ownership of Harry Frazee, sold the best hitter in the history of baseball to the Yankees…without even getting a single player in return.
This move was just the biggest in a long line of transactions—motivated purely by greed and money—that slowly dismantled baseball’s original dynasty.
Frazee only owned the club for eight seasons (1916-23), but his impact was felt for the better part of eight decades.
After winning the World Series in 1918, their fourth title in seven seasons, the Red Sox didn’t have another winning year until 1934.
By then, the image of the Red Sox as perennial losers was beginning to take hold in the minds of fans. This image was solidified as the Red Sox made just two World Series appearances from 1919 to 1967, finishing above .500 only around 43 percent of the time.
Ruth went on to revolutionize the game of baseball, setting innumerable records. He’s arguably the greatest (and certainly the most influential and even mythical) baseball player ever.