John Lackey
John Lackey is one of two Red Sox free agents on this list who were essential to the team winning a World Series and yet still remained disliked by most of the team’s fans. He spent the first eight seasons of his career with the Los Angeles Angels, gaining prominence as a rookie in 2002 when he won the clinching game seven of the World Series.
The Red Sox signed Lackey in the winter of 2009 to a five-year, $82.5 million contract. Language in the contract stipulated that if he missed a season due to injury, the final year of the deal would be at the league minimum. He pitched decently in his first season with the Sox, going 14-11 in 2010 before he had the worst season of his career in 2011 going 12-12.
Things quickly went from bad to worse as Lackey rapidly became unlikable to Red Sox fans and the Boston media. He had many testy exchanges with the Boston sports press from the beginning and things only went downhill. During the 2011 season, it was revealed that Lackey was divorcing his wife in the midst of her cancer treatments.
Regardless of the private details behind the story, it wasn’t a good look for him and it was only made worse by his comments in the press. After the season it was revealed that he was part of the now-infamous “fried chicken and beer” gang which also included Josh Beckett and Jon Lester. During the offseason fallout, Lackey had Tommy John surgery and missed all of the 2012 season.
However, he was seen by many drinking beers in the clubhouse during his rehab which only inflamed fan opinion against him. He was able to redeem himself in 2013; even though he was a pedestrian 10-13 with a 3.52 ERA in the regular season, he was excellent in the postseason, going 3-0 and winning the deciding game of the World Series.
Lackey came into the final year of his contract in 2014 making the league minimum and it was obvious he was unhappy about it. Still, he bounced back in a big way and was 11-7 in 22 starts for the Red Sox before he was traded to the Cardinals at the deadline for another pitcher who would end up helping the Red Sox win a World Series, Joe Kelly.
While John Lackey was a big reason why the team won the 2013 World Series, overall his time in Boston presaged the other free agent mentioned above who helped the team win but was never really embraced or liked by fans and the media.