2. The Jake Arrieta/Pedro Strop trade
Sometimes I think back to this trade and still can't believe that it really happened. The Dempster/Hendricks trade can be considered one-sided, but the Jake Arrieta trade is almost in a category of its own.
On July 2, 2013, Epstein struck a franchise-altering deal with the Baltimore Orioles, sending starting pitcher Scott Feldman and catcher Steve Clevenger for Arrieta and reliever Pedro Strop. Feldman was a rental who only made 15 starts for Baltimore while Clevenger had a journeyman career and only collected 485 major league at-bats. Meanwhile, Strop became one of the most effective relief pitchers of the decade and Arrieta ascended to near-godlike status.
Over six and a half seasons with Chicago, Strop posted a cumulative 2.90 ERA over 373 innings pitched, with 120 holds and 425 strikeouts. Arrieta was likely on his way to being designated for assignment by the Orioles before Epstein acquired him since he amassed a 5.46 ERA over three and a half seasons.
But things changed almost overnight after his change of scenery. He emerged as an ace-level power pitcher who anchored Chicago's rotation for the next four years. From June 21, 2015 - June 1, 2016, Arrieta was far and away the most dominant starting pitcher in the league, with a 1.13 ERA, two no-hitters, and a complete-game shutout against the Pittsburgh Pirates in the National League Wild Card game. The 11-strikeout effort secured the Cubs their first postseason victory in 12 years.
Whether Epstein and his staff saw something in Arrieta or he made the necessary adjustments on his own, this trade looks like nothing but gold in hindsight. Arrieta's reign of dominance lifted the Cubs' pitching staff and undoubtedly helped the team attract other top free agents like Zobrist, Lackey, and Jason Heyward heading into 2016.