These are the Red Sox to win it:
ORLANDO CEPEDA - 1973
The designated hitter position was created for guys like Cepeda. He was still an outstanding hitter, but he could barely move in the field. Cepeda was in his mid 30's and coming off of a season in which he hit just four home runs in 31 games. Boston signed him specifically to be their first DH and he came within minutes of being the first official DH. He was the first really good one though as he hit .289/.350/.444 with 20 home runs and 86 RBIs. He even received some MVP votes. It was his last great season.
JIM RICE - 1977
Rice was a still young hitter in 1977 who spent most of the season as the team's DH as a result of Carl Yastrzemski still going strong in left field. Fred Lynn and Dwight Evans were both terrific defensive players, so it was between DH and left field for Rice. He ended up playing in 116 games at DH and 44 in the outfield. Rice had his first truly great season in 1977 as he hit .320/.376/.593 while leading the league in home runs (39), total bases (382), and slugging percentage. He also drove in 114 runs and was an All Star while finishing fourth in the MVP vote.
DON BAYLOR - 1986
Another aging star whose career was extended by being a DH, Baylor was in his first, and only, full season with the Red Sox in 1986. He was coming off of a season in which he won the award for the Yankees in 1985. He was traded to the Red Sox for Mike Easler prior to the season and had a little better season in 1986, hitting .238/.344/.439 while helping to lead Boston to the World Series. He led the team with 31 home runs and drove in 94 runs. Baylor also won the Silver Slugger and picked up some MVP votes.
DAVID ORTIZ - 2003-2007, 2011, 2013, 2016
David Ortiz will go down as one of the greatest designated hitters of all time. He has won the award eight times, three more than the guy the award is currently named after. He might have won a couple more if injuries had not ended his 2012 season early, and he could have won in both 214 and 2015. Here is the breakdown on the years he won:
2003: .288/.369/.592, 31 home runs, 101 RBIs
2004: 301/.380/.603, 41 home runs, 139 RBIs
2005: .300/.397/.604, 47 home runs, 148 RBIs
2006: .287/.413/.636, 54 home runs, 137 RBIs
2007: .332/.445/.621, 35 home runs, 117 RBIs
2011: .309/.398/.554, 29 home runs, 96 RBIs
2013: .309/.395/.564, 30 home runs, 103 RBIs
2016: .315/.401/.620, 38 home runs, 127 RBIs