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Theo Epstein helped break two of baseball’s longest championship droughts.

Generations of Red Sox fans lived and died without seeing a Boston World Series title. After winning it all in 1918, the Sox hopelessness began.

The Beantown faithful had to wait 86 years until the team hoisted its next championship banner. The Massachusetts misfortune paled in comparison to the catastrophe in Chicago where the Cubs went more than a century – from 1909 to 2016 – without a title.

The executive who built the squads to break each team’s futility was Theo Epstein.

Hired by the Red Sox as General Manager in 2002, Epstein was the youngest man in baseball history to take control of personnel decisions. Thrust into a team devoid of championships, he nonetheless inherited a talented nucleus.

With Pedro Martinez, Manny Ramirez, and David Ortiz in the fold, Epstein traded for Curt Schilling and hired Terry Francona as manager. Then he assembled complimentary pieces that brought Boston its first World Series title since Woodrow Wilson occupied the White House.

The 2004 Red Sox team became the first – and as of yet the only – team to come back from a 0-3 playoff deficit to defeat the Yankees in the ALCS. On baseball’s biggest stage they then swept the St. Louis Cardinals in the World Series to break the 86-year drought.

Epstein wasn’t done. The following year he harvested Boston farm product Jonathan Papelbon. In 2006 he promoted minor leaguers Jon Lester and Dustin Pedroia. Then in 2007 his Red Sox team won it all again. Epstein left Boston after the 2011 season and saw the players he assembled take another title two years later.

Always eager for a challenge, Epstein took over as president of baseball operations with the Cubs. During his first three years, the Cubs finished last in the division. All the while, Epstein stockpiled young talent. Then in 2015 the Cubs reached the playoffs as a Wild Card team. Chicago advanced all the way to the National League Championship Series before being swept by the Mets.

In 2016 everything came together in the Windy City. The Cubs won 103 games to clinch the division, then rolled over the Giants and the Dodgers to reach the World Series. Facing a Cleveland team managed by old friend Francona, the Cubs triumphed in a thrilling seven-game tilt. Their 106-year drought was over. The city of Chicago rejoiced.

In a 12-year period two of baseball’s longest streaks of futility were broken with Epstein as the common denominator.

The Cubs enjoyed another division crown in 2017, followed by a 95-win season the ensuing year. In 2019 they slipped to third place. The shortened 2020 covid campaign resulted in another division championship and a disappointing playoff loss to the Marlins. In November that year Epstein resigned from his Chicago position.

With his place in baseball history secured, Epstein will someday be immortalized in Cooperstown.

Shown here is Epstein’s business card as president of baseball operations with the Cubs. The executive’s signature is deemed authentic by PSA/DNA services.

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Babe Ruth, both the man and the myth, remains one of baseball’s most important figures. Fans are well aware of his home-run hitting exploits. The first man to hit 60 homers in a season, Ruth set both the single-season and career marks for long balls and held them until the day he died.

The Yankee great started his career in Boston with the Red Sox. Winners of baseball’s first World Series in 1903, the franchise won five of the first fifteen Fall Classics. Three of those titles came with Ruth as their star pitcher in 1915, ’16, and ’18. On baseball’s biggest stage Babe went 3-0 with three complete games, a shutout, and a stingy 0.87 earned run average.

In December of 1919 Boston owner Harry Frazee sold Ruth to the rival New York Yankees. The move changed the course of both franchises.

Before Ruth arrived in New York, the Yankees never appeared in the postseason. With the Babe the team won 7 American League pennants and 4 World Series titles.

After selling Ruth, Boston’s fortunes also reversed. Once the game’s most dominating franchise, the Red Sox began a championship drought that some felt would never end.

The Sox futility became known as the Curse of the Bambino.

For 86 years Boston baseball fans suffered. Then in November, 2001 the team hired a man who would change the narrative – Theo Epstein.

Moving deftly, Epstein assembled a championship-caliber squad. In Epstein’s second year in charge the Sox made the playoffs but were ousted by the Yankees in the American League Championship Series.

The following year in 2004 history appeared to be repeating itself as the teams again faced off in the ALCS. The Yankees raced to a three-games-to-none lead. Epstein’s club fought back and vanquished New York to become the first team to comeback from such a deficit.

Riding the momentum, the Red Sox exorcised their demons in a four-game sweep of the St. Louis Cardinals. The Curse of the Bambino was lifted.

Shown here is a signed photograph of the Babe.

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Jon Lester was just 20-years old when the Boston Red Sox hired Theo Epstein as General Manager in 2004. The next two seasons Lester progressed to Double-A and Triple-A before making his MLB debut in 2006.

The left-hander went undefeated in 11 starts in 2007 as the Red Sox reached the World Series for the first time since 1986. With his team up 3-games-to-none, Lester got the start in Game 4. The 23-year old allowed three hits in 5 2/3 scoreless innings to earn the win that clinched Boston’s second championship in four years. The outstanding performance was a prelude of things to come for Lester.

When the pitcher and his team returned to the Fall Classic in 2013, Lester was named the Game 1 starter. He responded with 7 2/3 scoreless innings to set the tone. Three games later, the Series was knotted up at two games apiece. Boston turned to their postseason stalwart once more. Lester scattered four hits, struck out seven in 7 2/3 innings to put the Sox on the cusp.

Two days later Boston beat the Cardinals 6-1 to give Lester his second World Series ring.

When Lester became a free agent after the 2014 season, Epstein – now head of baseball operations with the Cubs – reunited with his former Boston mate. Immediately Chicago made two consecutive trips to the postseason. In 2016 Lester got the Game 1 start in the NLDS. He responded by holding the Giants scoreless in 8 innings of five-hit baseball. In the Championship Series Lester was again magnificent, allowing 2 runs in 13 innings with 9 strikeouts. His performance gained him the NLCS MVP Award.

Back on baseball’s biggest stage, Lester again proved pivotal. With his team down 3-games-to-1, Lester was the winner in the Cubs 3-2 Game 5 victory. Chicago pulled even in Game 6 then won it all in an extra-inning affair in Game 7. The momentous victory snapped Chicago’s 106-year championship drought and made Lester and Epstein three-time champions.

In the collection is this ticket signed by Jon Lester. The game was a memorable one in Lester’s career. Diagnosed with anaplastic large cell lymphoma after his 7th big-league win in 2006, Lester underwent aggressive chemotherapy treatment at Seattle’s Fred Hutchinson Cancer Research Center. By December, CT Scans showed no signs of the disease.

Working to regain his strength, Lester attended spring training in 2007 and plotted his big league return. He started at Single-A Greenville before going to Pawtucket on May 19th to face Triple-A hitters. The ticket shown here is from his first start for the PawSox.

Lester impressed the organization before the game even started. The Pawtucket squad had to make a 9-hour road trip to the contest in Ottawa. Rather than seek the comfort of a chartered flight, Lester stayed with his teammates in the longest bus ride of the season. He started the first game of the series, pitching 3 2/3 innings of one-hit scoreless baseball.

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In January, 2021 Major League Baseball hired Theo Epstein to research how rule changes would affect the game.

Commissioner Bob Manfred praised Epstein in a statement. “At the time of his hiring, I am grateful that he has accepted our invitation to complement our ongoing efforts and provide his insights on making the best game in the world even better for the next generation of fans.”

Working with analytics experts, Epstein helped usher in changes to speed up the pace of play and add excitement. He was intimately involved with the implementation of the pitch clock, pick off rules, and the banning of the shift. Though initially criticized by baseball traditionalists, the moves have been widely accepted as a needed improvement.

No matter what’s next, for Epstein, induction to Cooperstown is a matter of time for the man who resurrected two cornerstone franchises.

Shown here is an autographed photo of baseball commissioner Bob Manfred.