3) Getting Addison Russell in the Jeff Samardzija deal
By 2014, it was clear the Cubs were improving under Epstein and were not all that far off from contention. However, Chicago was far out of the playoff race in a tough NL Central, so Epstein took advantage of the opportunity to sell some veteran players.
Epstein made another great trade a few weeks prior to the 2014 deadline, sending a pair of starting pitchers in Samardzija and Jason Hammel to the Oakland Athletics in exchange for prospects Addison Russell and Billy McKinney, plus two others. It appeared that Epstein fleeced Billy Beane at the time, and nothing since has done anything to change that notion.
Samardzija was pitching very well at the time and his value had peaked, as he was traded from Oakland after half a season and struggled in 2015 with the Chicago White Sox. Hammel was terrible with the Athletics after a strong start to the 2014 season, and came back to the Cubs and pitched well in 2015 as an added bonus.
In exchange, the Cubs got two prospects who figure to be regulars in the majors for several years. McKinney has hit well in the minors and should start the season at Triple-A, while Russell started nearly the entire 2015 season at just 21 years old.
Russell posted 2.9 WAR according to FanGraphs in his first full season in the Majors, an impressive total for a young shortstop. Epstein dealt Samardzija and Hammel at exactly the right time, and got his shortstop of the future in return.
Next: Signing Jason Heyward