Mere minutes after the Cubs secured their first World Series title in 108 years, Theo Esptein was in absolute rare form. Grabbing every camera and microphone in his reach like a drunk sorority girl, Theo said “fuck you” to everyone who congratulated him, and announced he was going on a 3-month championship bender that would make J.R. Smith blush. Unprofessional? Probably. Hilarious? Absolutely. But there is no question in my mind that if anyone deserved to get shithoused on national television last night, it was Theo Nathaniel Epstein. I mean, just take a look at his resume:
42 years old. Two curses reversed. 194 combined years of heartbreak rectified. The sports landscapes of two cities changed forever.
Rome wasn’t built in a day, nor are World Championship teams born overnight. It takes patience, persistence and, as Terry Francona would eloquently say, cojones. Theo has plenty of all three, and he made it clear from the first day he was introduced as President of Baseball Operations in Chicago. On October 25th, 2011, after escaping a dumpster fire of a failure in Boston, Theo looked the city of Chicago in the eye and said that in five years he would make the Cubs a title contender. Naturally, he was scoffed at. The Cubs hadn’t seen a title in 103 years, nor had they even played in a World Series since 1945. More importantly, Theo was taking the helm of an organization that had a lot of overpriced veteran pitching, no farm system to speak of, and was in need of a complete personnel overhaul. Roll up your sleeves, we’re about to dive in.
Naturally, the Chicago fan base expected the young executive to make an immediate impact, executing the type aggressive moves that characterized his time in Boston. Theo did not disappoint. A strong believer in investing in young talent, he signed Starlin Castro to a monster 8-year/$60 million deal, one that many considered to be a no-brainer. More controversial was Theo’s decision to trade away Andrew Cashner, the 19th overall pick of the 2008 draft. A flame throwing righty, Cashner’s fastball lit up scout’s radar guns at 100 mph, averaging 99.4 out of the bullpen and 94.9 as a starter. Cubs fans saw a potential future ace in Cashner, but Theo felt it was imperative to bolster the farm system at the corner infield spots, an area that had been an Achilles heel in past Chicago lineups. On January 6th, the Cubs traded Cashner and outfielder Kyung-Min Na for starting pitcher Zach Cates and a raw, power-lefty first baseman by the name of Anthony Rizzo. Cashner has posted ERA’s of 4.35 and 5.25 the last two years between Miami and San Diego, while Rizzo has mashed more than 30 homers and 100 RBI’s in the same time span, collecting two of his three all-star nominations in the process. Ball don’t lie, and neither to the numbers.
Result: 61-101, 5th in NL Central
Meanwhile, a world championship pitching staff was being built brick by brick. In late 2012 Theo dealt longtime fan favorite Ryan Dempster for right handed pitcher Kyle Hendricks, in a move that left many in Chicago scratching their heads. The following year, the Cubbies move Scott Feldman and 2006 7th rounder Steve Clevenger to Baltimore in exchange for Perdo Strop and a then-mediocre starting pitcher named Jake Arrieta. The Cubs also quietly select Kris Bryant 2nd overall in the 2013 draft.
Result: 66-96, 5th in NL Central
In the first half of 2014, Cubs ace Jeff Samardzija turns down a 5-year/$85 million extension, making it clear that it was time for the team to move on from the Shark. Theo packages him and Jason Hammel and sends them to the A’s in exchange for a package of players that includes the #3 prospect in baseball, Addison Russell. Despite being a project as a late first-rounder, the Cubs select Kyle Schwarber 4th overall in the 2014 draft. The fan base is naturally outraged; Theo essentially tells them all to go fuck themselves. We also get our first taste of the walking defensive highlight reel some call Javier Baez, who showed some pop with his bat despite hitting a mere .169. Result: 73-89, 5th in NL Central
Theo get busy in the offseason. Prior to the 2015 season, Cubs outbid everyone for ex-Red Sox Jon Lester and David Ross. Theo also adds some veteran bats and great glue guys in Dexter Fowler and Miguel Montero. Joe Maddon opts out his contract with the Tampa Bay Rays and signs with the Cubbies for $25 million. In his opening presser, Joe closes it out by buying every reporter in the building a shot and a beer, and just like that the stage has been set for a wild Cubs season. Cubs win 97 games and make the playoffs for the first time since 2008. Arrieta is unhittable, Rizzo and Bryant solidify baseball’s premier 1-2 punch, and Schwarbombs everywhere as the Cubs bushwhack the entire league en route to their first NLCS appearance since 2003. There Chicago would finally fall to the Mets, but they sent a clear message to the league and the entire fan base: the Cubs are finally good again.
Result: 97-65, 3rd in NL Central, lost in NLCS
Theo rounds out a potent Cubs lineup by signing Ben Zobrist to a heavy short-term contract, and bolsters the defense with journeyman Jason Heyward, who would share the outfield with Fowler and Jorge Soler aka the Cuban Missile Crisis. With the outfield complete, the 5 year plan was in place. The North Side squad had compiled the most devastating lineup in the league, with three of the league’s premier starting pitchers to boot. They were a wire-to-wire favorite. Even down 2-1 in the NLDS, and down again 3-1 in the World Series, there was never a doubt who the best team in baseball. So even when they stumbled, Theo never lost faith in the guys on the field. It was all just part of the plan. Enjoy the champagne, Theo. We’ll see you at winter meetings.