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Top 15 Worst Pitchers In Boston Red Sox History

One of baseball’s all-time storied franchises, the Boston Red Sox formed in 1901. The club did not go by “Red Sox” until 1908. Other titles included the Boston Americans, Boston Pilgrims and Boston So

One of baseball’s all-time storied franchises, the Boston Red Sox formed in 1901. The club did not go by “Red Sox” until 1908. Other titles included the Boston Americans, Boston Pilgrims and Boston Somersets. Whatever the team name, 115 years provides countless chances to employ a complete dud on the mound.

The Red Sox have enjoyed a number of Hall of Fame hurlers in their history, but it takes more than few clunkers to undergo an 86-year stretch without a World Series victory. Some might point to the Curse of the Bambino. Babe Ruth was a prolific Red Sox pitcher before becoming the Yankees’ Sultan of Swat. His ghost cannot take all the blame for heartbreak after heartbreak

Boston finally broke through during the magical 2004 campaign. The organization has added two more titles since, most recently in 2013. Several pitchers included played during the post-drought years. The front office didn’t stop making mistakes, but they did a better job covering their tracks.

Whether it’s due to underperforming on a massive contract, giving up soul-crushing home runs, or striking fear in their own fans’ hearts the second they take the mound, these players are the Top 15 Worst Pitchers in Red Sox History.

15 Steve Avery (1997-1998)

via boston.com

Steve Avery shares a name with the man recently made famous by Making a Murderer. Unlike the documentary’s theories regarding the Manitowoc Police Department, framing Avery’s pitches never worked out for Boston catchers. Avery, a third overall pick in 1988, became a young phenom with the Atlanta Braves. History does not serve him well. Thanks to a rapid career descent, he fades away from the Braves’ historic pitching staff of Greg Maddux, Tom Glavine and John Smoltz. Steve Avery’s performance and mechanics struggled following a muscle strain below the armpit of his pitching arm. Atlanta had a surplus of pitching talent in 1997, allowing the Red Sox to take a chance on Avery as a free agent. The ailing pitcher’s ERA ballooned from 3.83 in seven years with Atlanta to 5.64 during a two-year Boston stint. Avery went 16-14 and never made a meaningful impact in the major leagues again.

14 Larry Andersen (1990)

via realclearsports.com

Larry Andersen appeared in 18 total games for the Red Sox – fifteen in the regular season and three during the playoffs. He pitched well in the regular season, posting an ERA of 1.23. The problem is that Boston traded minor leaguer Jeff Bagwell for a 37-year-old temporary reliever. Andersen bolstered the bullpen, but failed in the playoffs. He managed a 6.00 ERA while being swept by the Oakland Athletics. That’s the extent of his Red Sox career. Unfortunately, the loaner goes down as one of the words trades in team history. Bagwell won the 1991 NL Rookie of the Year, 1994 NL MVP, three Silver Sluggers and one Gold Glove. He retired in 2006 with 449 home runs and 1,529 RBIs. That’s a 15-year, potential Hall of Fame career in exchange for 18 games during an unsuccessful championship run.

13 Heathcliff Slocumb (1996-1997)

via redsoxphotos.photoshelter.com

The Red Sox would not have broken the curse without Heathcliff Slocumb, but he didn’t appear on their championship team. He retired after the 2000 season. His inclusion on the list runs almost inversely to the Larry Andersen debacle. Slocumb played a season and a half for the Boston Red Sox. Although he converted 31 saves for the team in 1996, his performance slipped miserably the following season. Through 49 games, he had 17 saves in 22 attempts and a 5.79 ERA. That’s an uninspiring 77.3% success rate. Boston decided to stop conducting 9th inning batting practice for opposing teams and shipped Slocumb to Seattle. The team received Derek Lowe and Jason Varitek in return. Both men played pivotal roles in Boston’s 2004 Championship winning season. The fans tortured by Slocumb in 1997 could never have foreseen that. He played for four teams in his final three years, serving mostly as bullpen depth.

12 Skip Lockwood (1980)

via alchetron.com

Born in Norwood, Masschusetts, Skip Lockwood returned home in his final season of a 12-year career. The Boston homecoming was not a successful one for the injury-riddled reliever. The Kansas City Royals drafted Lockwood with the intention of turning him into a third baseman. He could not hit at the professional level. Despite a respectable career ERA, pitching did not go much better for Skip. The bulk of his work as a starter came early with Milwaukee, where he went 28-55. He moved to the bullpen during the mid-70s, posting an ERA of 1.49 in 1979. Boston took a risk on the small ’79 sample size (42.1 IP). There was trouble from the start. Manager Don Zimmer and Lockwood argued early on about his use in a 15-1 losing effort. Zimmer considered him as a prima donna. The Red Sox used Skip sparingly and he failed to make the most of his opportunities. He pitched three more innings than in 1979, but nearly quadrupled his earned runs allowed and dropped his strikeouts by more than 30. The Red Sox released him in early April the next year.

11 Jerry Stephenson (1963, 1965-1968)

via ecrater.com

Jerry Stephenson served as a forgettable Boston reliever during the 1960s. He made a brief appearance at the major league level in 1963 before spending all of 1964 with a Boston’s minor league affiliate. He moved back and forth between the majors and minors throughout his career. His best year came in 1967, in which he posted a 3.86 ERA and appeared in one game during Boston’s World Series loss to St. Louis. It was the only season he finished with an ERA below five. His other significant seasons with the organization included a 6.23, 5.83, and 5.64 ERA. He pitched a total of 9.1 innings for the Seattle Pilots and Los Angeles Dodgers in 1969 and 1970 respectively. His playing career ended after three more years in the minors.

10 John “Way Back” Wasdin (1997-2000)

via outlet.historicimages.com

Unless you’re carrying lumber to the plate, “Way Back” is never a good nickname for a pitcher. The unfortunate moniker stems from Wasdin’s habit of giving up long balls. He surrendered more than 1.5 home runs per nine innings pitched, a total of 54 for the Red Sox over four seasons. The reliever never finished lower than fourth on the team in total home runs given up, routinely beating out teammates with more innings. He also finished with the Boston’s highest ERA of eligible pitchers during the 1998 campaign. The Red Sox should have known what they were getting after Wasdin gave up 24 dingers in his final year with the Oakland Athletics. The team had their fill by mid-2000, when they traded Wasdin to Colorado. He jumped between the minors, majors and Japanese baseball until his retirement in 2010.

9 Byung-Hyun Kim (2003-2004)

via ebay.com

Byung-Hyun Kim is a story of lost potential and big game nerves. After start to the solid postseason for the Diamondbacks in 2001 (one hit and zero earned runs in 6.1 innings), he singlehandedly tried to hand the World Series to the opposing Yankees. He allowed five earned runs for a 13.50 ERA in two appearances. Kim recovered nicely with an All-Star appearance in the 2002 season, but floundered once again during the team’s lone postseason series. The Red Sox traded for Kim in the middle of the 2003 season to install him in their rotating committee of closers. He rewarded them with 16 saves. Come playoff time, Kim blew a save against Oakland in Game 1 of the ALDS. When the crowd booed his introduction during Game 3, he promptly flicked them off. He didn’t pitch again in the playoffs. Kim signed a two-year, $10 million dollar contract in the offseason. Injuries limited him to 17.1 innings in 2004. The front office traded him to Colorado in 2005, an admission of the failed contract.

8 George Winter (1901-1908)

via sabr.org

George Winter was a member of the original Red Sox American League team. Winter has a career record of 83-102 and is tied fourth all time for losses in a Boston uniform (97). Winter lost the second half of the 1902 season due to Typhoid Fever. Although he pitched on 1903’s opening day and also clinched the pennant, he did not appear in the World Series. Boston’s big three of Cy Young, Bill Dinneen and Long Tom Hughes started every game. Winter participated only as a ticket-taker – the game has clearly changed since the turn of the 20th century. A bad stomach forced him to miss a chunk of the 1906 season, but he was ineffective even when he managed to take the mound, going 6-18. Boston placed Winter on waivers during the 1908 season after a 4-14 start. He went 1-5 with his new team, the Detroit Tigers, despite a 1.60 ERA the rest of 2008. He played two more seasons for the Eastern League Montreal Royals before calling it a career.

7 Matt Clement (2005-2006)

via bostondirtdogs.boston.com

Boston signed Matt Clement to a three-year, $25.8 million contract prior to the 2005 season. At the time, it was the most expensive contract the team had give to a free agent pitcher. He immediately repaid them with an All-Star appearance. It was the only highlight. Injuries and poor pitching marred Clement’s career in Boston. A Carl Crawford line drive struck him in the head during the second half of 2005. A shoulder injury ended his 2006 season after 12 games. He had gone 5-5 with a 6.61 ERA and a career high WHIP. His injury prevented him from appearing in the 2007 season. After three years, $25.8 million resulted in 44 starts, 18 wins and a 5.09 ERA. Clement received spring training contracts but never caught on with another team.

6 Matt Young (1991-1992)

via redsoxphotos.photoshelter.com

Matt Young reached his first and only All-Star game during his 1983 rookie season with Seattle. He never recaptured that form in his career. A quick glance at the numbers indicates his failures with the Boston Red Sox. After joining the team as a free agent, Young went 3-11 with a 4.91 ERA over two years. Matt Young’s most famous game tells more about his experience in Boston than further statistical analysis ever could. Young threw a no-hitter in 1992 and lost 2-1. His erratic control directly contributed. He allowed seven walks. Not only did he lose, Matt Young also failed to gain an official no-no. A committee had changed the rule the previous year to require a full nine innings of work and the opposing Cleveland Indians did not have to bat in the 9th inning. The no-hitter that wasn’t truly embodies Matt Young: plenty of hype and potential but a Red Sox loss in the end.

5 Jack Russell (1926-1932, 1936)

via sports.mearsonlineauctions.com

Jack Russell never had a winning season for the Red Sox. One time he came within three games. So close. He started his career 0-5 at age 20 during the 1926 season. It’s not as if the zero in the loss column can be chalked up to growing pains. It was his lowest ERA and WHIP until the 1933 season with the Washington Senators. Russell is tied for 7th most losses in a single Red Sox season. He lost 20 games out of 30 starts, but that isn’t his worst winning percentage, as Russell went 6-14 during another season. Just for good measure, Russell returned to Boston in a 1936 trade and went 0-3. His win-loss record with the Red Sox is 41-94. Add up all of his other wins in his 15-year career and Jack Russell still doesn’t eclipse his loss total solely with Boston.

4 Daisuke Matsuzaka (2007-2012)

via ftw.usatoday.com

Admittedly, Daisuke Matsuzaka ranks so poorly due to a combination of recency bias and the bloated price tag it took to sign him. Before the Red Sox even acquired Dike-K’s talents, the team had to pay a $51.11 million posting fee. A $52 million contract followed, totalling $103.11 million. Matsuzaka quickly established himself as an ace. He went 15-12 his first year before a remarkable 18-3 sophomore season. Then, the wheels fell off. Dice-K suffered from an assortment of arm injuries. When he wasn’t injured, the import was plagued by lackluster play. He went 17-22 in his next four seasons with the team. His ERA climbed from 2.90 in 2008 to 5.76 in 2009. 2012 culminated in 11 total games and an 8.28 ERA. He joined the Mets in free agency and went 6-6 over two seasons. Dice-K’s initial success prevents him for being considered an unredeemable bust, but his final years in Boston qualify him for highway robbery.

3 Eric Gagne (2007)

via bostondirtdogs.boston.com

Eric Gagne spent half a year in Boston after joining the team at the trade deadline. The Red Sox pegged the former Cy Young winner and 3-time All-Star as the setup man to Jonathan Papelbon. The move made the bullpen look like the best in the majors. Papelbon had a 2.15 ERA and 23 saves at the time while setup man Hideki Okajima was sitting at a staggering 0.87 ERA. Although several years removed, Gagne brought the all-time consecutive saves record. Gagne unfortunately did nothing but disappoint. He finished the regular season with a 6.75 ERA, career-high WHIP, and 14 ER in 18.2 innings pitched. In his best year with the Dodgers, he gave up 11 ER in 82.1 innings pitched. During the postseason, Gagne gave up three runs in 3.1 innings, earning a loss in the ALCS. He averaged almost a run per inning leading up to the World Series. The Red Sox scarcely used him in their championship sweep of Colorado. He pitched in one inning. Boston did not elect to resign him following the season.

2 Mike Torrez (1978-1982)

via baseball.wikia.com

Mike Torrez lasted 18 years in Major League Baseball, going 185-160 with a 3.96 ERA. The numbers aren’t amazing, but also aren’t an eyesore. He compiled his most wins (60) with the Boston Red Sox. Why is Mike Torrez a top-5 worst Red Sox pitcher of all time? Bucky F-in' Dent and the 1978 Boston Massacre. Boston had a lead as high as 14 games in the middle of summer. By September 7th, their bitter rivals had whittled the lead down to four games. Mike Torrez took the mound against his former Yankees in the first game of a four-game series. He lasted only one inning. The Yankees won the game 15-3 and swept the series in what became known as the Boston Massacre. The teams battled neck and neck for the rest of the season. A late surge by the Red Sox forced a one-game playoff. During the seventh inning, unlikely hero (or villain) Bucky Dent stepped up the plate and hit a three-run homer off Mike Torrez. It was a pivotal moment in the Yankees 5-4 victory that capsized Boston’s title dreams. New York went on to claim their second consecutive World Series. Boston waited another 26 years.

1 Red Ruffing (1924-1930)

via saulwisnia.blogspot.com

Red Ruffing holds the top two slots for most losses by a Red Sox pitcher in a single season. He followed up a 10-25 season in 1928 with a 22-loss effort in 1929. Win-Loss record can be an arbitrary statistic, but Ruffing kept his ERA under four only once with Boston. It wasn’t just a case of playing for a bad team. Ruffing’s performance begged for history to forget his days as a player. A 39-96 record in seven seasons with a team is enough to run anyone out of the league. By the way, Ruffing is in the Hall of Fame. He found a second life after Boston traded him for Cedric Durst, a lifetime .244 hitter. Mike Torrez earned the number two spot by giving up a home run to Bucky Dent. Ruffing saw Torrez’s measly home run and raised him 231 wins, six All-Star nominations and seven World Series victories with the hated New York Yankees. Red spent fifteen years in Pinstripes, but accumulated only 28 more losses than he did in half the time with Boston. He lowered his ERA by more than a point and was credited with at least one win in six of seven World Series. It’s the ultimate stab in the back to the Red Sox faithful.

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Top 15 Worst Pitchers In Boston Red Sox History