10 of Epstein's best moments with the Cubs

November 19th, 2020

CHICAGO -- The Theo Epstein era on the North Side began with an encounter in a Chicago coffee shop. Nine years ago, a Cubs fan recognized Epstein and greeted the baseball executive, who tried to play coy.

Epstein was in town then ahead of being hired to lead the Cubs' front office. There will be no mistaking him in Chicago from here on -- not after all that he accomplished as the team's president of baseball operations. Epstein stepped down from that post on Tuesday, handing the keys to the top office to his long-time general manager Jed Hoyer.

As the Cubs enter a new era of leadership, here are 10 of the best moments and moves of Epstein's time with the North Siders:

10) Signing Ben Zobrist
There have been free-agent hits and misses throughout Epstein's tenure. There have been criticisms over the blockbuster Jason Heyward contract, but his leadership and his famous Game 7 speech have made a massive impact beyond his numbers. The Yu Darvish deal has looked better by the year, especially with him finishing as the runner-up for the National League Cy Young Award in 2020.

One signing that will forever be reviewed warmly by Cubs fans was the four-year deal with Zobrist, who wanted to join the fold after Chicago's exciting 2015 campaign. Zobrist became a clubhouse leader and a versatile weapon for the North Siders, bouncing up and down the lineup and playing all over the field. In '16, Zobrist won the World Series Most Valuable Player Award after hitting .357, including delivering the go-ahead RBI double in the 10th inning in Game 7.

9) Finding a leadoff man in Dexter Fowler
On Jan. 19, 2015, Epstein swung a trade with the Astros, reeling in Fowler for Dan Straily and Luis Valbuena. It was a move that brought a catalyst to the top of the Cubs' lineup and helped the group grow into a run-churning force over the next two seasons.

Former Cubs manager Joe Maddon liked to say, "You go, we go," to Fowler, and that proved prescient. In Game 7 of the 2016 World Series, Fowler led off with a home run against Corey Kluber, and it was clear that Progressive Field was packed with Cubs fans. He went 3-for-5 in that legendary game, sealing his place in franchise lore.

8) Acquiring Kyle Hendricks
At the July 31 Trade Deadline in 2012 -- Epstein's first year at the helm -- the Cubs dealt pitcher Ryan Dempster to the Rangers for a pair of prospects. One was Hendricks, a pitcher who relied on finesse rather than power. The Cubs did their homework and were told that Hendricks was someone to bet on given his work ethic, character and command.

Eight years later, Hendricks has developed into one of the game's elite strike-throwers and is on a path to becoming a Cubs legend. He has a 3.12 ERA in seven MLB seasons and a 3.12 ERA in 12 playoff games. Hendricks won an ERA title (2.13) in 2016, and he took the ball in Game 7 of the World Series. Hendricks was, without question, one of the great finds during Epstein's tenure.

7) Bringing David Ross into the fold
Ross was only with the Red Sox for part of the 2008 season -- a small part of Epstein's nine-year run atop Boston's front office. During the '13-14 seasons, Ross was back with Boston and he was used as the primary catcher for Jon Lester. So eight days after the Cubs signed Lester on Dec. 15, 2014, Chicago inked Ross, too.

That partnership helped not only shape the Cubs for the next two years, but eventually the future of the franchise. Ross' teammates and fans embraced him as "Grandpa Rossy," and he became a hero with his homer off Andrew Miller in Game 7 of the 2016 World Series. Ross became the Cubs' new manager before the '20 season.

6) Hiring Maddon as manager
When former Rays GM Andrew Friedman left for the Dodgers during the 2014-15 offseason, Maddon opted out of his contract with Tampa Bay. Rumors that Maddon was being targeted by the Cubs quickly became reality, as Chicago parted ways with Rick Renteria and hired Maddon on Nov. 2, 2014.

Two years to the day of that announcement, the Cubs hoisted their first World Series trophy since 1908. Maddon's player-friendly, innovative and free-spirited style was a perfect fit for a young Cubs team that was full of talent, but low on experience. Maddon oversaw one of the great five-year runs in team history before his exit after the 2019 season.

5) Drafting Kris Bryant
Epstein and his front-office crew inherited a massive undertaking when they arrived to the Cubs. The rebuild would require stripping down the Major League club and acquiring a pile of prospects who could grow together. The 101-loss showing in 2012 helped expedite that process by netting the Cubs the No. 2 overall pick in the MLB Draft.

Houston picked Mark Appel with the first overall selection and the Cubs got their man in University of San Diego slugger Bryant. Chicago focused on building its roster through impact position players (Kyle Schwarber was drafted one year later) and Bryant was a critical piece to that plan. After winning the Golden Spikes Award in 2013, he won the NL Rookie of the Year Award in '15, then the NL MVP Award and a World Series by '16.

4) Getting Anthony Rizzo back
Epstein recently described Hoyer as being a "very tough" negotiator when the latter was leading the Padres' front office. In December of 2010, Hoyer managed to acquire Rizzo from Epstein's Red Sox in the trade that sent Adrián González to Boston. Epstein tried to get the Padres to take Lars Anderson, but Hoyer wouldn't budge.

Flash ahead to Jan. 6, 2012, when Hoyer was reunited with Epstein in the Cubs' front office, and Chicago pried Rizzo away from the Padres in a deal for pitcher Andrew Cashner. Once a core piece for Epstein in Boston, Rizzo was now part of the Cubs' future. In nine years with Chicago, Rizzo has become a leader, while winning multiple Gold Glove Awards and playing a leading role in the '16 World Series triumph.

3) The Lester signing
As the story goes, Maddon walked back into the hotel lobby in San Diego during the 2014 Winter Meetings and told reporters, "We won the baseball lottery." Those words came after news arrived that the Cubs had signed free-agent pitcher Lester to a blockbuster six-year, $155 million deal. A last-place Cubs team that lost 89 games in '14 had just reeled in the biggest free-agent prize, and it changed the course of team history.

With Lester in the fold, it was clear: Winning was now expected, and he would lead the way. Lester has logged over 1,000 innings for the Cubs with a 77-44 record and a 3.64 ERA. He has been an All-Star and a Cy Young Award contender. And, he posted a 2.44 ERA in a dozen playoff games (including six Game 1 starts and an appearance in Game 7 of the 2016 World Series).

2) The Jake Arrieta trade
It is one of the great trades in Cubs annals, and will go down as one of the more lopsided deals in baseball history, too. On July 2, 2013, the Cubs sent Scott Feldman and Steve Clevenger to the Orioles for pitchers Arrieta and Pedro Strop. In that one move, Chicago's century-long drought was one step closer to ending.

Feldman and Clevenger produced 0.8 WAR (per Baseball Reference) combined in their time with Baltimore. Arrieta alone netted 20.0 WAR for the Cubs. He posted a 2.73 ERA over parts of five seasons with Chicago, winning the NL Cy Young Award in 2015 (22-6, 1.77 ERA with a 0.75 ERA in the second half). On Oct. 7, 2015, Arrieta went into Pittsburgh and struck out 11 in a shutout in the NL Wild Card Game, making it clear that these Cubs were here to stay.

Arrieta's presence and dominance helped shape the culture about the ballclub, but Strop's importance should not be overlooked, either. Epstein said it was Hoyer who "pounded the table" to land Strop, who became a leader in his own right and one of the most reliable and consistent relievers in Cubs history. In over 411 games for Chicago, Strop turned in a tidy 2.90 ERA.

1) Ending the 108-year drought
The Curse of the Billy Goat. The black cat on the field. The Bartman Game. Cubs history was littered with lore and legend and myth for a team that went more than a century without winning a World Series. Epstein did not erase that part of the team's pages, but he helped eradicate the Lovable Losers label.

All the decisions and moves and philosophies culminated in one of the greatest World Series that baseball has ever seen. And just to drive Cubs fans mad, Cleveland ran out to a 3-1 lead before the North Siders could finish the job. Epstein would have loved to have brought home multiple trophies, but even one seemed unimaginable for the Cubs fan base for multiple generations.

"It was such a special time. Such an unexpected time," Epstein said. "And it felt like the lines between fans and front-office members and players were blurred, because we were all part of this club that was in on a secret. I think we all kind of knew what was about to happen maybe before the rest of the baseball world did."