If it seems like a lot of the players on this list were acquired by the Red Sox during my childhood in the 1980s and 1990s, that’s because for whatever reason they continually made these same mistakes over and over again during those years. While some long in the tooth players, like Jeff Reardon (1990-1992) worked out, most ended up panning out the way Frank Viola did.
Viola had been a very successful pitcher in the 1980s, most notably for the Minnesota Twins with whom he won a World Series in 1987. He was the MVP of that series and also won the AL Cy Young award with them in 1988. After a couple of seasons spent with the New York Mets, the Red Sox signed Viola in 1992.
Similar to Fergie Jenkins, Viola wasn’t terrible with the Red Sox, but he was far from great and not what I’m sure they expected they were getting based on what he’d done in the past. He’d won 163 career games before joining the Red Sox but only won 25 with them in the three seasons he spent in Boston between 1992 and 1994.
Viola went 13-12 in 1992 and 11-8 in 1993. In 1994 he went 1-1 in six starts before missing the rest of the season after requiring Tommy John surgery. He left the Sox after 1994 and finished his career with two more injury-plagued, forgettable seasons.