As a team, the Red Sox have finished under .500 only 38 times in 112 seasons.  The worst team ever in terms of both winning percentage and number of defeats was the forgettable 1932 squad, led by former Boston outfielder Shano Collins for the first 55 contests before getting fired and replaced by former utility infielder Marty McManus.  The team finished a dismal 43-111 and dead last in the eight-team American League, 7.5 games behind the seventh place Chicago White Sox and 64 games behind the first place New York Yankees, who finished 107-47, a near-mirror record compared with Boston.

The Sox were actually in the midst of a 15-year stretch between 1919 and 1933 in which they finished under .500 every season.  Eight times, the team finished under the .400 mark, including six straight seasons between 1925 and 1930.  Another particularly bad stretch of seasons happened between 1959 and 1966, when the team went eight straight years under .500, including an abyssmal 62-100 in 1965 with a team that include manager Billy Herman and outfielder Carl Yastrzemski.

Speaking of 100-loss seasons, seven teams in franchise history have earned this mark of shame, including the 1932 and 1965 teams.  Also in the mix are teams from 1926 (46-107), 1925 (47-105), 1906 (49-105), 1927 (51-103), and 1930 (52-102).  12 teams in franchise history have finished last in the league or division.  Surprising, this does not include the 1965 team, which finished three games ahead of the Kansas City Athletics for ninth place in a ten-team league.

It should also be noted that the last time the Red Sox suffered back-to-back losing seasons was a stretch of three sub-.500 seasons between 1992 and 1994.  All three teams were managed by Hobson and the best finish was an 80-82 mark in 1993.  Surprisingly, a three-year stretch between 1906 and 1908 in the only other time, beyond the aforementioned streaks of bad luck, that the franchise team suffered back-to-back losing seasons.  Of note, the 1907 team, which finished 59-90, was managed by four different people that season, including player-manager Cy Young.

So, in no particular order, are five candidates for consideration:

1. Don Zimmer

Younger Red Sox fans might remember him more as the old guy who Pedro Martinez tossed to the side in the midst of an on-field melee at Fenway Park during the 2003 ALCS, but “Zim” led Boston over four years at the helm, taking over for Darrell Johnson after the latter was fired midway through a disasterous 1976 campaign. In 715 games as manager, he won 411 contests and finished with better than 90 wins in every season between 1977 and 1979 before being dumped unceremoniously seven games before the end of the 1980 campaign. He also served 2-1/2 seasons under Johnson as Boston’s third base coach and returned for one season in 1992 as Butch Hobson’s bench coach. Older fans often remember him as the manager who watched the Red Sox blow a 14-1/2 game lead in July of 1978, and then witnessed Bucky Freakin’ Dent hit a home run in a one-game playoff at Fenway to lose the AL East crown that same season, but that team also managed to win 99 games, the fourth-most wins ever in a season in franchise history. He was, in the words of Johnny Pesky: “…an innovator, a student of the game, and an excellent day-to-day manager.”[1]

2. Earl Wilson

Wilson owns the distinction of being the first African-American pitcher in Red Sox team history, breaking the color barrier by hurling a scoreless one-inning relief appearance in late July of 1959; three days later, he made his first ever start. He also threw a no-hitter at Fenway Park in June of 1962, helping his own cause with a home run, and becoming the first black major league pitcher to throw an American League no-hitter. In seven seasons with Boston, Wilson won 56 games for clubs that finished at or near the bottom of the league standings. After a trade to Detroit midway through the 1966 campaign, Wilson’s career took off as he further blossomed and won another 64 games with the Tigers. Wilson was also regarded as one of baseball’s greatest power-hitting pitchers, hitting 35 home runs during his career and all but two of them while in the game as a pitcher. He even hit two in one game with the Red Sox in 1965.

3. Dutch Leonard

Leonard pitched for six seasons in Boston between 1913 and 1918, posting 90 wins and a 2.14 ERA with 769 strikeouts in that span. He also won both of his World Series starts, once in 1915 and another in 1916, as the Red Sox won back-to-back world championships. He may be best remembered, however, for posting an amazing 0.96 ERA in 1914, the modern baseball record, while going 19-5 in 36 starts. He also threw two no-hitters in his Red Sox career, once in August of 1916 and again two years later in June of 1918. Unfortunately, due to shipbuilding and millitary obligations, he missed most of the 1918 season, losing out on the opportunity to be part of a third world championship.

4. Bill Lee

“Spaceman” made a name for himself more due to his unique personality but few people remember that he was actually a great pitcher during the mid-1970s, winning 17 games in three straight seasons between 1973 and 1975. After beginning his career in the bullpen, Lee was made a permanent fixture of the rotation in 1973 and responded with 16 wins in 33 starts and an overall 17-11 record with a 2.75 ERA, enough to earn him his only All-Star appearance. After posting a 17-15 record the following season, he went 17-9 in 1975 during Boston’s pennant-winning season. 16 of those wins came between May and August to help the Red Sox distance themselves from their division rivals; he also enjoyed a stretch of eight straight appearances between early July and mid-August that included seven starts without a loss, including four straight complete game victories, and compiled a 6-0 record with a 3.14 ERA during that span. He would finish his Boston career with 94 wins and a 3.64 ERA to his credit, along with enough off-the-wall comments made during his career to create a Fenway Park legend.

5. Mike Greenwell

“Gator” became a Fenway Park fixture in 1987 and spent ten seasons with the club, averaging .303 at the plate while hitting 133 home runs with the only team he ever knew. An All-Star twice, he provided a solid and reliable presence in the team’s lineup during his tenure, perhaps best demonstrated with the fact that he averaged a strikeout only once every 3-1/2 games and posted a .368 career on-base percentage, twice recording an OBP of .400 or better. Greenwell finished fourth in his rookie season for American League Rookie of the Year honors and finished second a year later in the MVP race to Jose Canseco. In most years, he was the team’s everyday left fielder, following in the hallowed footsteps of legends like Ted Williams, Carl Yastrzemski, and Jim Rice, and managed a respectable .982 fielding percentage playing in front of the wall at Fenway Park. He is also one of just 18 Red Sox players to hit for the cycle and hit an inside-the-park grand slam against the Yankees at home in September of 1990.

[1] Pesky, J. and Pepe, P. Few and Chosen: Defining Red Sox Greatness Across the Eras. 2004, Triumph Books, Chicago, IL. 170 pp.