Dennis Eckersley
While his time in Boston spanned from 1978 to 1984 and straddled the two decades, this list is the best place to put Dennis Eckersley since his best seasons as a starter happened in a Red Sox uniform in the late 1970s. Acquired in a trade with the Cleveland Indians in March 1978 (precipitated by Eck’s wife having an affair with one of his Indians teammates), the trade paid immediate dividends for Boston.
Eck went 20-8 with a 2.99 ERA and 162 strikeouts in his first season with the Red Sox in 1978 and helped them win 99 games before they fell to the Yankees in the infamous one game playoff at the end of the season. He was almost as good in 1979 when he went 17-10 with a 2.99 ERA and 150 strikeouts. He tailed off a bit in 1980 with a 12-14 records, an ERA of 4.28, and 121 strikeouts.
From 1981 to 1984, though, he struggled and posted a 35-38 record with a dismal 4.66 ERA and 316 strikeouts. He was eventually traded during the 1984 season to the Chicago Cubs for Bill Buckner. Eck would eventually go on to become one of the greatest closers in baseball history with the Oakland A’s and would be elected to the Baseball Hall of Fame when his career was over.
However, he was a vital part of the rotation for those great 1978 and 1979 Red Sox teams that came up just a bit short of the postseason.