Spoiler alert: every Red Sox player on the BBWAA ballot this year is a World Series champion. However, what sets John Lackey apart is that he won championships with multiple teams, and that’s why he probably has a better chance of getting elected to the Hall of Fame than anyone else on this list.
Lackey was a rookie when the team then known as the Anaheim Angels won their first and only championship in 2002. He finished fourth in AL Rookie of the Year voting that season after posting a 3.66 ERA over 18 games, including the first complete game of what would turn out to be a 15-year career.
Following the 2009 season, Lackey was considered the best free-agent starting pitcher on the market, and the Red Sox signed him to a five-year deal worth $82.5M. Following the 2011 season, he underwent Tommy John surgery, forcing him to miss the entire 2012 season. He returned in 2013 and posted a 3.52 ERA and threw multiple complete games for the first time since 2008. That October, he made history as the first starting pitcher in MLB history to be the winning pitcher in deciding games of the World Series with two different teams.
The Sox traded Lackey to the St. Louis Cardinals at the 2014 deadline and he signed a lucrative two-year deal with the Chicago Cubs ahead of the 2016 season. That October, he and former Sox teammate Jon Lester were champions once again, as the Cubs ended their 108-year World Series drought.
All time, Lackey ranks 57th in strikeouts, 88th in starts, 15nd in wins, 162nd in innings pitched, and 195th in pitcher WAR.