Cubs: Dexter Fowler trade was Theo Epstein’s crowning achievement

Jon Lester might have been the most significant free agent signing in Chicago Cubs history, but I’d argue it wasn’t the crowning achievement of the Theo Epstein era.

That designation goes to the team’s acquisition of Dexter Fowler. The Cubs acquired Fowler from the Houston Astros the very same offseason they signed Lester to what was then the richest deal in franchise history.

Chicago sent Luis Valbuena and Dan Straily to Houston in exchange for Fowler, who first broke into the majors with the Colorado Rockies in 2008. The deal was meant to give the Cubs more steadiness in the outfield, but it ended up providing the North Siders with so much more.

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Fowler immediately set the tone at the top of the lineup with quality at-bats, speed and even some power. His debut season was an indicator of things to come.

The Atlanta native was a model of durability in his first season with the Cubs, playing 156 games in 2015. Fowler walked 84 times, hit 17 homers and stole 20 bases, giving Chicago a legitimate leadoff presence.

As strong as Fowler’s 2015 was, however, it almost wasn’t enough to ensure he would return to the North Side. In fact, Fowler turned down a far more lucrative offer from the Baltimore Orioles in order to return to the Cubs.

“More lucrative” is probably an understatement, in this case. Fowler was reportedly on the cusp of a three-year, $33 million deal with the Orioles. Instead, he re-signed with Chicago for one year and $8 million, with an option for the following season.

Fowler’s selfless display clearly resonated with teammates, who welcomed him back into the fold.

This was the birth of the “You Go, We Go” moniker that would be attached to Fowler.

The veteran center fielder had the best year of his career in 2016, posting an .840 OPS in addition to a career-high 129 wRC+ value. Fowler cut down on his strikeouts and upped his walk rate, earning the first All-Star selection of his career.

But Fowler had more heroics in store come October. He had nine hits and four RBI in Chicago’s NLCS win over the Los Angeles Dodgers. Fowler’s leadoff homer in Game 7 of the World Series also spurred the Cubs to their early lead in what amounted to one of the greatest games in MLB history.

The beloved outfielder joined the St. Louis Cardinals in 2017, and Chicago’s ensuing outfield dilemma only does more to underscore his importance to those Cubs teams.

Cubs center fielders ranked 16th in fWAR between 2017 and 2019. It was not until Ian Happ’s breakout 2020 that Chicago finally got some production from that position.

Moreover, Chicago lacked steady on-base options from the leadoff spot. Cubs leadoff hitters had a .324 OBP in 2017 and a woeful .294 OBP in 2019.

The lack of production at the top of the lineup resulted in tremendous offensive inconsistencies, and those inconsistencies forced the team to juggle the futures of guys like Kyle Schwarber (who, with Lester, is now with the Washington Nationals), Kris Bryant and Javier Baez, among others.

In hindsight, the Fowler acquisition looks all the more important given the current state of the organization. He was far more than just a leadoff hitter, but an unselfish leader who gave the Cubs a certain fire and swagger in the clubhouse. The desire to win surpassed all individual concerns.

The Lester signing set things in motion for the Cubs to be contenders, but the Fowler trade was one of the under-the-radar moves that so often births a champion.