In the year 2000, the two most cursed franchises in baseball were the Chicago Cubs and Boston Red Sox. Given their history of bad luck, many believed that it would be another hundred years before either of these big market teams would win a championship. While Jon Lester did not break these curses (he wasn't in the Majors when Boston broke it in 2004), he played a significant role in two squads that had been struggling for decades.

Lester was a Second Round pick by the BoSox in 2002 and joined the main roster in 2006. While he played well, he had enlarged lymph nodes that required off-season treatment. Fortunately, Lester recovered and returned to the Red Sox the following summer, where he gained a win in the 2007 World Series, his first championship. After that, Lester became a high-end starter.

In 2008 and 2009, Lester won a combined 31 games with 377 strikeouts. He went to his first All-Star game in 2010, led the AL in SO/9 (9.7), and was fourth in Cy Young voting. He struck out 225 batters, with a 3.25 ERA and a career-high 19 wins. He was an All-Star again in 2011 (15-9, 3.47 ERA) but slipped in 2012 (9-14, 4.82 ERA), which was cause for concern in Fenway.

However, in 2013, Lester rebounded and went 15-8. His postseason was phenomenal as he went 4-1, including two wins in the World Series with a 0.59 ERA. He went to the All-Star game again in 2014, but the struggling Red Sox traded him to the surging Athletics for their playoff run. Although Oakland did not get past the first round, Lester's overall season was his best in years, as he finished fourth in Cy Young voting with an overall performance of 16-11, 220 strikeouts, and a 2.46 ERA.

Lester became a free agent and signed with the Chicago Cubs. He had his ups and downs with the Cubs, but his up years were memorable. He won 19 games in 2016 with a 2.44 ERA and was again an All-Star. Most importantly, Lester led Chicago to their first World Series win in over a century, and he won the NLCS MVP and was named the Babe Ruth Award winner. He was an All-Star again in 2018 (his fifth), but he struggled afterward and retired after brief runs in Washington and St. Louis.

Lester retired with three World Series rings, an even 200 wins, and 2,488 strikeouts.

Jon Jay had a 12-year career as an outfielder, but he was not known for his power-hitting. He hit only 37 home runs throughout his career. However, he did have seven seasons in which he had over 100 hits and batted over .290 five times. Jay's willingness to help his team is also reflected in his ranking in the top 100 all-time in Hit by Pitch. He spent most of his career with St. Louis, where he played for six seasons and won a World Series in 2011. He also played for San Diego, Chicago (NL), Kansas City, Arizona, Chicago (AL), and Los Angeles (AL). Jay had a lifetime batting average of .283 with 1,087 hits.

John Axford, a Canadian baseball player, started his career in the Majors by replacing Hall of Fame reliever Trevor Hoffman in Milwaukee. Although he was a starting pitcher in the Minors, Axford performed well as a relief pitcher, saving 24 games in 2010 and leading the National League with 46 saves the following season (2011). His impressive performance earned him the NL Rolaids Relief Award and a ninth-place finish in the Cy Young voting.

In the subsequent season, Axford recorded 35 saves but his ERA was over four. Unfortunately, he was unable to regain his previous dominance, but he still managed to accumulate 144 saves during his 11-year career. In addition to Milwaukee, he played for St. Louis, Cleveland, Pittsburgh, Colorado, Oakland, Toronto, and the L.A. Dodgers.

Joakim Soria began his career in the Mexican League before being selected in the Rule 5 Draft by the Kansas City Royals from the San Diego Padres organization. This turned out to be a wise investment for KC as Soria finished seventh in the American League Rookie of the Year voting in 2007, with 17 Saves. Over the next three seasons, Soria established himself as one of the best closers in baseball, earning All-Star Game selections in 2008 and 2010 and recording 105 Saves. Although he finished tenth for the Cy Young in 2010, he was arguably better in his first All-Star year, with 42 Saves, a 1.60 ERA and a WHIP of 0.861. However, Soria's performance slumped in 2011 (28 Saves, 4.03 ERA, 1.276 WHIP), and he missed the entire 2012 season due to Tommy John Surgery to repair a torn UCL. Although he made a comeback, he was never the same as before.

Over the next nine seasons, Soria played for nine different teams (Texas, Detroit, Pittsburgh, Kansas City again, Chicago (AL), Milwaukee, Oakland, Arizona, and Toronto), all out of the bullpen where he was sometimes again the closer. During this period, he had 69 Saves and a total of 229. While Soria never regained his past glory in Kansas City, he was good enough to find work for nearly a decade after.