Damon came to the Red Sox as a fresh-faced 28-year old in 2002 and left four years later looking like a caveman, but along the way he became one of the most popular players on the team. That’s why the fan base was stung when he bolted to the rival New York Yankees, drawing the scorn of fans that felt betrayed by what they perceived as a greedy decision to accept a lucrative contract from the “Evil Empire.”
Despite the bitter divorce, we can’t forget that Damon had an excellent run in Boston. He made his first of two All-Star teams during his initial season with the Red Sox and performed well enough to receive MVP votes in each of his last two years in Boston.
Damon was considered to be among the elite lead-off hitters in the game, producing a .295/.362/.441 slash line as a member of the Red Sox. He had modest pop in his bat that rarely led to high home run totals, but he still racked up his fair share of extra-base hits. Damon tallied at least 32 doubles in every season he spent in Boston and led the league with 11 triples in 2002.
We will always remember Damon as an invaluable member of the 2004 World Series team. The highlight of his postseason run came in the decisive Game 7 of the ALCS against the Yankees, when Damon smashed a pair of home runs and drove in six RBI to cap off the greatest comeback in playoff history.
If there is one knock against Damon that prevents him from ranking higher on this list, it’s his defense. He had the speed to track down fly balls, but opposing base runners were never shy about taking an extra base against his noodle arm. Damon was among the best at his position at the plate, but his weak throwing arm also made him one of the worst rated defensive players by many of the advanced metrics.