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Photo: David J. Phillip/Pool Photo via USA TODAY Sports Images

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Looking Back on the Cubs’ Ascension During the Theo Epstein Era

Thank you, Theo.

Cubs fans knew this development was inevitable, but we thought we had another year before it became official.

The Theo Epstein era has officially come to an end in Chicago.

Before the news became official, Epstein wrote a letter to his Cubs family that was obtained by The Athletic. He said the first day fans are welcomed back to Wrigley Field, he and his family will walk to Clark and Addison to attend what will likely be an exciting day for players and fans.

It’s a bittersweet day for Cubs fans. It was known that Epstein wouldn’t remain with the Cubs beyond the 2021 season, but the shocking news of Epstein stepping down as the Cubs President of Baseball Operations came today.

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One thing Epstein offered for Cubs fans throughout his tenure complete transparency.

He continued that trend in his press conference on Tuesday.

There were a few things to take away from his press conference, including the transition to new President of Baseball Operations Jed Hoyer, Epstein’s ‘third chapter’ in baseball, his love for the city of Chicago, and being grateful for the opportunity he was given nine years ago.

Epstein said he wants to get the full Bleacher Bum experience now that he’s not affiliated with the Cubs.

All in all, it was a press conference full of laughs and a trip down memory lane.

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Thank You, Theo

There aren’t enough words to fully explain how thankful I am for Epstein’s work with the Cubs.

I remember when Epstein was introduced as a member of the Cubs front office.

Everything he said that day came true. The Cubs finally won the coveted World Series fans desired for decades.

Under Epstein, the Cubs qualified to play postseason baseball five times in his nine seasons. The Cubs made the postseason four consecutive seasons, a feat the franchise had never accomplished in its history that dates back to 1889.

Epstein changed the culture on the North Side. He set the tone the moment he arrived, bringing years of experience and success from his days with the Red Sox.

He will always be remembered for how he built the eventual World Series-winning roster in 2016.

Roster construction starts with the Anthony Rizzo trade.

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When Epstein arrived, the Cubs farm system ranked near the bottom of the league.

Does anyone remember Brett Jackson or Josh Vitters? That’s how bad the system was.

In Epstein’s first three seasons, the Cubs had highly-touted prospects coming up the ranks thanks to his work despite not having many assets to move. However, Rizzo was the first big name added to the farm by Epstein via trade.

With the Cubs rebuilding, they were able to move pieces to contending teams and receive assets at the trade deadline during consecutive seasons.

In 2012, the Ryan Dempster trade brought Kyle Hendricks to the Cubs.

The next mid-summer trade cam in 2013. Epstein made arguably his best move as the President of Baseball Operations when he executed a trade with the Orioles that turned out to be very lopsided in the Cubs’ favor. The Cubs sent Steve Clevenger and Scott Feldman to Baltimore in exchange for Jake Arrieta and Pedro Strop.

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The summer of 2014 was fun. The Cubs were not good but you could see change coming to Wrigley Field with breakout seasons from Rizzo and Starlin Castro. They won more games than they did the previous four seasons.

The Cubs promoted highly-touted prospect Javier Baez to the majors and the front office made another blockbuster trade at the deadline.

Theo and co. sent Jason Hammel and Jeff Samardzija to the Athletics for top prospect Addison Russell, Billy McKinney, and Dan Straily. The Cubs eventually signed Hammel back via free agency.

In addition to drafting Kris Bryant with the second overall pick in the 2013 MLB Draft, the Cubs selected Kyle Schwarber fourth overall in the 2014 MLB Draft.

All these names became known commodities quickly in Chicago. Over the course of discussing these transactions, I just named you the starting infield of Game 7 of the 2016 World Series: Rizzo, Baez, Russell, and Bryant.

It took Epstein three years to compile what eventually became a World Series-contending roster. To put it in perspective, it took the Cubs 108 years to win the World Series. Epstein truly struck gold on every transaction early in his tenure.

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Epstein’s first mega free-agent signing came in the form of Jon Lester. Theo later added Ben Zobrist, Jason Heyward, and John Lackey, all members of the 2016 championship roster.

There are so many moves that led to the Cubs’ competitive window, but landing Lester and Epstein’s savvy way of bringing in quality prospects via trade or the draft from the moment he stepped foot into Wrigley Field speaks volumes.

I think I speak for all Cubs fans when I say that we will forever be grateful for your time on the North Side, Theo.


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