The Chicago Cubs won Game seven of the World Series on Wednesday, ending the longest drought in MLB history. In one of the most exciting games in baseball history, the Cubs defeated the Cleveland Indians in extra innings and were thus crowned World Champions. GM Theo Epstein has assembled a team in Chicago that is built for the long haul, a team that can truly compete for the next five World Series. How did Theo Epstein assemble such a talented squad of players?
The answer may seem simple, but in truth, is a lot harder than it sounds. Epstein nailed his draft picks and won more of his trades than he lost. Before the 2016 season commenced, Epstein knew his team had a chance to compete, and went out and signed players that could fill the missing roles in the team. It is a recipe for success that Epstein established at his previous tenure in Boston where he had broken another curse in 2004 before winning the 2007 World Series with Boston as well.
Epstein began his most recent tenure in Chicago in October 2011. He would proceed to finish in the cellar of the division his first three seasons before getting to the NLCS in 2015 and winning the World Series in 2016. This is important because those three seasons in the cellar led to very nice draft picks for Epstein and the Cubs organization.
2012, aka Epstein’s first draft, led to the Cubs drafting Albert Almora Jr. with the 6th overall pick. The 2013 MLB Draft saw the Cubs owning the second overall pick, which would be used on Kris Bryant. 2014 sparked controversy for the Cubs, as the organization drafted Kyle Schwarber, which was seen as a reach for the Cubs at the time by pundits. These three first rounders were all on the World Series squad, with Bryant and Schwarber both contributing heavily with their production at the plate.
Epstein was a trade machine in Boston, and the same philosophy carried over to his tenure in Chicago. Epstein was a master of selling players at their peak and actually netting a strong return in terms of prospects. For example, the Cubs traded Scott Feldman to help shore up Baltimore’s rotation in exchange for reliever Pedro Strop and starter Jake Arrieta. Arrieta had never pitched with great success in Baltimore, averaging an ERA of 5.46 while playing for the Orioles. Since joining the Cubs, his ERA since 2013 has averaged out to 2.52 over his last three seasons.
Arrieta is not the only present core Cub to be received in a trade. Anthony Rizzo, a stud first base prospect at the time, was picked up from San Diego for a package built around Andrew Cashner. Cashner  had some inconsistent success in San Diego, but Rizzo is currently one of the top first basemen in all of baseball. The Cubs traded starter Ryan Dempster, who was having a very strong season in his own right, to the Rangers in exchange for Kyle Hendricks. Addison Russell was also picked up in a trade by Epstein, who had to give up Jeff Samardzija and Jason Hammel (yes, the same Hammel who would go on to resign with the Cubs in the following offseason) for the package built around Russell.
Epstein also made the right decision in regards to personnel choices on the roster. Epstein had acquired a plethora of talent at nearly every position in the minors. Epstein leaned on this talent as he traded veterans to be replaced by the inexperienced rookies. Epstein dumped Starlin Castro so both Addison Russell and Javier Baez could have starting positions in the Cubs middle infield. Plenty of talent were traded or axed for marginal returns to make room for the future stars of the Cubs. Yet, despite all these wily veterans being traded, none of the talent really amounted to much after the trades. The biggest names include players like Justin Ruggiano, Marlon Byrd, Carlos Zambrano, and Alfonso Soriano.
Looking at all this wheeling and dealing, Epstein is bound to come across a couple trades that could be viewed as losses right? In all honesty, there is really only two trades that could be viewed as losses and both trades have reasonable defense for the action. First, was DJ LeMahieu being traded to the Rockies. LeMahieu has since produced an All-Star season playing second base for the Rockies, but the trade can be defended as Epstein already had his future middle infield in Castro and Baez (with Russell on the way). The only other lost trade was trading Welington Castillo to Seattle for next to nothing. Truth be told, Castillo never really was an offensive threat in Chicago, and the Cubs had already turned to alternatives to replace him at the catching position.
In truth, Epstein has been nearly flawless in constructing this 2016 World Champion squad. A few things shook out in his favor, like Jake Arrieta shaking off his kinks and becoming an ace pitcher. That being said, every team needs a little luck to win in the playoffs. Epstein’s impact trades and draft picks have setup the Cubs for success for the next five years. Now the final test will be to see if Epstein and the Cubs can sustain this success for the next decade or so, potentially putting together a team that can be a true dynasty, much to the dismay of the rest of the NL Central.