September 28, 2016
The Chicago Cubs have announced that President of Baseball Operations Theo Epstein, General Manager Jed Hoyer, and VP of Player Development and Amateur Scouting Jason McLeod have all signed contract extensions with Theo Epstein's deal being a reported 5yr/$50MM deal making him the highest paid baseball executive by a wide margin (breaking Andrew Friedman's previous 5yr/$35MM record).
After ending the curse in Boston, Epstein came to north side Chicago with the intent of doing the same thing for the Cubs. Five years later, and the Chicago Cubs have gone from a club stuck in the cellar to the best team in Major League Baseball. With dynamic, young players entrenched all over the roster, the Cubs aren't looking to win just one title. As he proved in Boston, Epstein is capable of building teams that can compete for multiple championships.
After officially becoming the highest paid executive in baseball and only second to Phil Jackson (who has won 11 championships as a Head Coach) in any of the major sports, it's time he is officially recognized as not only the best executive in baseball, but in any sport ever. Only championships will validate the claim, but Epstein isn't the one that takes the field in the 9th inning of a one-run game or makes the strike three call on a pitch outside with the game on the line. He's the one that has set up his franchise for success more than any other executive in sports history (although current Warriors GM Bob Myers is making a case for himself now that KD plays at the Oracle).
From drafting Kris Bryant over Jon Gray (when many executives favored Gray's arm) to trading Steve Clevenger and Scott Feldman for the 2015 Cy Young Winner Jake Arrieta and dominant reliever Pedro Strop. There are a multitude of other moves the Cubs' front office has made over the last five years that have put them in the position they're in now: on the brink of winning multiple World Series championships.
How this affects the future outlook of the Cubs: Anytime a team can keep a top-tier front office together, it's a good thing. Now that Epstein and company are officially under contract for the foreseeable future, the team can expect more advantageous trades, smart drafting decisions, and overall organization improvement (fixing Wrigley Field, overhauling the front office resources, better live-game experience for fans) over the coming years. Rome wasn't built in a day, and now the Cubs' stalwart front office can keep on building behind the best baseball executive of all-time.