Tom Yawkey died in 1976, and his wife Jean R. Yawkey took control of the team until her death in 1992. Their initials are shown in two stripes on the Left field wall in Morse code. Upon Jean's death, control of the team passed to the Yawkey Trust, led by John Harrington. The trust sold the team in 2002, concluding 70 years of Yawkey ownership.
In 1994, General Manager Lou Gorman was replaced by Dan Duquette, a Massachusetts native who had worked for the Montreal Expos. Duquette revived the team's farm system, which during his tenure produced players such as Nomar Garciaparra, Carl Pavano and David Eckstein. Duquette also spent money on free agents, notably an eight-year, $160 million deal for Manny Ramírez after the 2000 season.
The Red Sox won the newly realigned American League East in 1995, finishing seven games ahead of the Yankees. However, they were swept in three games in the ALDS by the Cleveland Indians. Their postseason losing streak reached 13 straight games, dating back to the 1986 World Series.
Roger Clemens tied his major league record by fanning 20 Detroit Tigers on September 18, 1996 in what would prove to be one of his final appearances in a Red Sox uniform. After Clemens had turned 30 and then had four seasons, 1993–96, which were by his standards mediocre at best, Duquette said the pitcher was entering "the twilight of his career." Clemens went on to pitch well for another ten years and win four more Cy Young awards.
Out of contention in 1997, the team traded closer Heathcliff Slocumb to Seattle for catching prospect Jason Varitek and right-handed pitcher Derek Lowe. Prior to the start of the 1998 season, the Red Sox dealt pitchers Tony Armas, Jr. and Carl Pavano to the Montreal Expos for pitcher Pedro Martínez. Martínez became the anchor of the team's pitching staff and turned in several outstanding seasons. In 1998, the team won the American League Wild Card, but again lost the American League Division Series to the Indians.
In 1999, Duquette called Fenway Park "economically obsolete" and, along with Red Sox ownership, led a push for a new stadium.
On the field, the 1999 Red Sox were finally able to overturn their fortunes against the Indians. Cleveland took a 2–0 series lead, but Boston won the next three games behind strong pitching by Derek Lowe, Pedro Martínez and his brother Ramón Martínez. Game 4's 23–7 win by the Red Sox was the highest-scoring playoff game in major league history. Game 5 began with the Indians taking a 5–2 lead after two innings, but Pedro Martínez, nursing a shoulder injury, came on in the fourth inning and pitched six innings without allowing a hit while the team's offense rallied for a 12–8 win behind two home runs and seven RBIs from outfielder Troy O'Leary. After the ALDS victory, the Red Sox lost the American League Championship Series to the Yankees, four games to one. The one bright spot was a lopsided win for the Red Sox in the much-hyped Martinez-Clemens game.
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