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Jon Lester played 15 of his 17 big league seasons with the Red Sox and the Cubs and earned a World Series ring with each club. Winner of 200 regular-season contests, he left baseball as one of its most respected big-game pitchers.

Lester broke in with the Red Sox in 2006 by winning seven of his nine decisions. A cancer diagnosis late in the year ended his season and delayed his start in 2007.

After beating the disease, Lester posted a spotless 4-0 record in 11 starts in 2007 as the Red Sox reached the World Series. In an exclamation point to his triumph over cancer, Lester won the final game of the season when Boston completed a sweep of the NL champion Colorado Rockies. His 5 2/3 scoreless inning were just the beginning of his postseason dominance.

Over his next seven seasons Lester blossomed one of the game’s frontline starters. From 2008-2014 he averaged 15 wins per year, made three All star teams, pitched a no-hitter, and finished in the top-4 of Cy Young balloting twice. In 2013 he led the Sox to back to the Fall Classic where he went went 2-0 with a 0.59 ERA for the world champs.

The Red Sox dealt him to Oakland at the 2014 trade deadline for outfielder Yoenis Cespedes. Lester won 6 games down the stretch to help the A’s reach the postseason.

A free agent after the year, Lester was wooed by former Boston GM Theo Epstein who was then in charge of the Cubs. Their reunion proved fruitful. In 2015 Lester went 19-5 with a 2.44 ERA to finish second in the Cy Young race. His performance helped Chicago win 103 games.

In each of the three postseason series Lester was the choice to start Game 1. In the NLDS he twirled 8 innings of scoreless baseball. The NLCS MVP, Lester started two games and pitched to a 1.38 ERA.

In the Fall Classic, with their championship hopes on life support, the Cubs turned to Lester. Down 3-games-to-1 needing a win to stay alive, Lester resuscitated his team with 6 innings of four-hit baseball to get the win.

Three days later Chicago toppled Cleveland in a thrilling extra-inning affair to win the World Series. The left-hander earned his third World Series ring.

Lester continued pitching effectively, winning 44 games over the next three years. In covid-shortened 2020, he made 11 starts to help the Cubs reach the postseason for the fifth time in six years.

A free agent at season’s end, Lester left Chicago and signed with the Washington Nationals. He made 16 starts before being dealt to St. Louis at the trade deadline. A winner in four of his five decisions down the stretch, Lester again helped his club play in October.

On November 3, 2021 the Cardinals granted the 37-year old free agency. Two months later Lester announced his retirement.

Jon Lester left the game with three World Series rings and exactly 200 career victories. Renown as a big-game pitcher, Lester set the record with 12 Game 1 playoff series starts. In six World Series games he recorded a stingy 1.77 ERA.

Despite the five All Star appearances, the no-hitter, two titles with Boston, one in Chicago and his 200 wins, Lester appears short of Cooperstown.

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 in in 2006, Lester underwent aggressive chemotherapy treatment at Seattle’s Fred Hutchinson Cancer Research Center. In December CT Scans showed no signs of the disease.

After regaining his strength, Lester attended spring training in 2007 and started his path back to the bigs at Single-A Greenville. On May 19th the Sox sent him to Pawtucket 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 faced 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. Lester got off the bus and pitched 3 2/3 innings of one-hit scoreless baseball.

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Theo Epstein assembled the 2004 Boston Red Sox team that broke an 86-year World Series drought. After the parade, Epstein went back work.

In search of more talent, Theo turned to the team’s farm system. He promoted reliever Jonathan Papelbon, second baseman Dustin Pedroia, and starter Jon Lester. By doing so he reloaded and rejuvenated the roster.

By 2007 the team reached their second World Series in four years.

Playing against the National League champion Colorado Rockies, Epstein’s team won the first three games. One win away from the title, manager Terry Francona gave the ball to 23-year old Lester.

The southpaw allowed three hits in 5 2/3 innings to earn the give the Red Sox the title.

Epstein left Boston after the 2011 season. The roster he assembled won a third Fall Classic title in 2013. On the mound that October Lester was the star. He won two games, struck out 15, walked only one and allowed just one runner to cross the plate.

The following season the Red Sox dealt Lester to Oakland at the trade deadline. Pitching to a 2.35 ERA, Lester won 6 games down the stretch to help the A’s reach the postseason.

A free agent at year’s end, Lester reunited with Epstein in Chicago with the Cubs. With Lester in the fold the team immediately the Cubs made two consecutive trips to the postseason.

In the 2016 NLDS Epstein and the Chicago braintrust gave Lester the ball for Game 1. He responded by holding the Giants scoreless in 8 innings of five-hit baseball. In the LCS Lester was again magnificent, allowing 2 runs in 13 innings. His performance gained him the NLCS MVP Award and pushed his team to the Fall Classic.

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 both Lester and Esptein three-time champions.

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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When Jon Lester earned the win in Game 5 of the 2013 World Series, he became the second Red Sox southpaw to earn three Fall Classic victories. Historic in its own right, the feat is even more special considering the left-handed hurler who did it first: Babe Ruth.

Ruth worked hard for his first World Series win, going the distance in Boston’s 14-inning Game 1 victory in 1916. In Game 1 of the 1918 Series Ruth pitched a six-hit, complete-game shutout over Hippo Vaughn and the Cubs. Four days later he scattered seven hits in 8 innings of work to win Game 4.

Lester earned his first World Series win in Game 4 of the 2007 Sox sweep of the Colorado Rockies. Seven years later the left-hander bested Cardinals ace Adam Wainwright in the 2013 Series opener. When he pitched 7 2/3 innings of one-run ball against St. Louis in Game 5, Lester joined Ruth.

Shown here is a photograph signed by Ruth in 1947.

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Jon Lester finished his 16-year big league career with a 200-117 record. The win total makes him one of five hurlers to end their career with exactly 200 victories.

George Uhle, Adam Wainwright, Chuck Finley, and Tim Wakefield are the others.

In the collection is a letter from legendary autograph collector George Hipp written to Uhle. Hipp requests the pitcher’s autograph in 1957. In that decade through the 1960s Hipp was a prolific letter-writer in his attempt to obtain the autograph of every living player.

The image above shows Hipp’s successful attempt to secure Uhle’s signature.

The pitcher writes, “Dear Mr. Hipp – Very sorry this letter did not get into my hands until today. Will be most pleased to accommodate you at any time – Sincerely Geo Uhle.”

Hipp’s letter is dated February 15, 1957 while Uhle has penned the date of April 5, hence his apology for not tending to the request earlier.

Similar letters to Hipp can be found on the pages of Larry French and Lon Warneke.