5. Hiring Joe Maddon
A big part of a great baseball team is the guy calling the shots in the dugout. Joe Maddon and the Cubs is another example of a match made in heaven. Maddon had just completed his ninth season as the Tampa Bay Rays skipper when he opted out of his contract. Although Epstein had already committed to Rick Renteria as Chicago's manager, he went back on his word when Maddon became available and struck a five-year deal with the then two-time manager of the year recipient.
Maddon utilized more of a vibes-based and traditional approach to managing his clubs as opposed to modern analytics. He kept things light with costume-themed road trips and off-the-wall anecdotes during his press conferences. Maddon's former catcher David Ross described his approach as "letting things happen organically," but that his unpredictable nature also kept opposing teams guessing.
It was a great fit because the Cubs already had most of their star players on the roster like Kris Bryant, Anthony Rizzo, Jake Arrieta, and Kyle Hendricks. Maddon stepped in to set the tone and let the players be themselves. The results speak for themselves. During Maddon's tenure in Chicago, which lasted from 2015-2019, the Cubs had four 90+ win seasons with two first-place finishes in the NL Central, a World Series title, and three trips to the NLCS. Epstein made a tough call but the right one to fire Renteria and bring in Maddon when he did.
4. Signing Ben Zobrist
Another insanely valuable addition to the Cubs' roster was utility man Ben Zobrist, who Epstein inked to a four-year pact prior to 2016. Even though Zobrist was 35 years old and heading into the twilight of his playing career, he was worth every penny of the $56 million Epstein gave him.
After 9 years playing for Maddon in Tampa Bay, and half a season with the Kansas City Royals that won him his first World Series, Zobrist reunited with his old manager to give the Cubs their everyday second baseman. But those years in Tampa Bay saw Maddon utilize the switch-hitting Zobrist in every spot in the batting order and virtually every defensive position on the field aside from catcher and pitcher. He played all of those positions at a high level and used his elite hitting skills to get on base, hit for power and contact.
This unique versatility came in handy on multiple occasions in Chicago, and nobody knew how to better utilize it than Maddon. Zobrist primarily played second base (at All-Star level) for the first half of the 2016 season, but later transitioned into the outfield when Javier Baez emerged and began warranting more playing time. In addition to significant time in left field (418.2) and second base (2099.2), Zobrist logged innings at right field (898), first base (25), shortstop (15), and one at pitcher as a Cub.
Zobrist's most important contributions came in the 2016 postseason when he delivered season-saving hits in the NLDS and in game 7 of the World Series, the latter of which secured him the World Series MVP Award.
Although Zobrist had some really nice seasons on paper, he is the type of player where statistics do not give you the entire picture. He was available for the Cubs at the perfect time and his four-year tenure with the team is a perfect showcase of why he was one of the most skilled and valuable position players of the 21st century.