The 2020 MLB season can be summed up using a handful of adjectives. Weird, yes. Short, of course. Sad, for us fans, absolutely. But for the Chicago Cubs, sitting here in late November of 2020, there’s only one word I can think of. Change. Change is upon the great franchise who has been one of the most dominant teams since 2015. Missing the playoffs just one time in the past 6 seasons and obviously bringing a championship home for the first time in over a century. But why will there be change heading into the 2021 season? Well, for the first time since 2011, the Cubs will be entering the year without the greatest baseball mind to ever live. Theo Epstein has stepped down one year before the end of his contract and is handing over the reins, and a laundry list of to-dos, to Jed Hoyer. He’ll have some extremely difficult decisions to make over the next few years with many star Cubs players’ contracts coming to an end all at the same time. But making difficult decisions and masterful moves are what’s expected from the GM/President of Baseball Operations in the great city of Chicago. It’s what Theo did to get the Cubs to where they’ve been over the past 6 seasons. Before we look forward at what’s to come for the Cubs, let’s take a look back and rank Theo Epstein’s Top 5 Moves.
5) Hendricks Heist
Theo’s first Summer in Chicago started off hot. While many may not have known at the time, this trade to acquire The Professor in July of 2012 has turned out to be one of the bigger steals in Theo’s tenure. He traded 35-year-old Ryan Dempster for Christian Villanueva and the 23-year-old Kyle Hendricks from Dartmouth. A household name for 2 prospects. In Chicago, in the 2000’s, fans weren’t used to this. The former GM and ownership loved to sign big-named older players to seemingly spark some fan interest. Not anymore. Not under Theo’s watch. Hendricks has gone on to be the backbone of the Cubs Rotation and among the league leaders in ERA (12th) and WAR (11th) among pitchers since joining the Chicago Cubs.
4) Capturing Chicago’s Captain
Not even 3 months into his time in Chicago, Theo made a splash. Trading away Andrew Cashner and Kyung-Min Na for Zach Crates and Anthony Rizzo. Just 5 years earlier, Theo Epstein drafted Anthony Rizzo while in Boston. He got his guy and Chicago just got the future face of the franchise. Rizzo is a 4X Gold Glover, 3X All-Star, and ranks 4th in WAR since 2013 among first baseman. But he means so much more to the city than any accolade or stat can describe. Year after year he’s a finalist for the Roberto Clemente award that he won in 2017. After battling cancer at a young age, Anthony Rizzo started his own foundation helping raise money for cancer research and on top of this, he constantly brightens kids’ days at local hospitals. He embodies what it means to be a Chicagoan and will hopefully spend his long career in this city with an eventual statue being placed outside the stadium with a “C” on his chest.
3) 1st Round Royalty
Evaluating and developing talent in the MLB is not an easy thing to do. Theo and team’s success at the top of the draft was a huge part of the overall success and the World Series Championship in 2016. Here’s a list of Theo’s first round draft picks as a Cub:
2012: Albert Almora Jr. 2015: Ian Happ 2018: Nico Hoerner
2013: Kris Bryant 2016: N/A 2019: Ryan Jensen
2014: Kyle Schwarber 2017: Brendan Little 2020: Ed Howard
Three of those draft picks played huge roles in the Cubs World Series run, four of them are currently impacting the success of the team, and two of them have extremely bright futures. I’d say the Theo regime has been successful at the top of the draft, wouldn’t you?
2) Chapman to Chicago
The World Series plan for Theo was all falling into place. The young guys he acquired had developed nicely and he had obtained some established Major Leaguers heading into the season. But there was one piece missing in the puzzle. A fireball throwing monster to closeout games without the stress and anxiety that Hector Rondon was bringing to the mound. And once again, Theo proved that he was here to win and would do anything it took to do so. Trading away top prospects Gleyber Torres, Billy McKinney and Rashad Crawford along with pitcher Adam Warren for Aroldis Chapman. Theo was officially putting all his chips in the middle and telling Cubs’ fans that 2016 would be the year. I’m sure Gleyber Torres will see consistent success at the MLB level and make multiple All-Star appearances, but you make that trade 100 times out of 100 to win a World Series and break a century long curse.
1) Jon Lester: The Start of it All
Theo’s career with the Cubs is littered with strategic moves that make you question the sanity of the GM on the other side of the phone. Getting future MLB Cy Young Winners and All-Stars for a couple of buckets of balls and some bubble gum. So why is a free agent signing the #1 Theo Epstein move? Because it meant more than that. The Chicago Cubs won the Jon Lester Sweepstakes in December of 2014. Theo and team wooed Lester with a virtual World Series experience that showed him on the mound in Game 7 winning it all for a city that has been cursed by farm animals, feral cats, and a guy with a Walkman (And yes, he did pitch in Game 7 of the World Series). Signing the biggest free agent in baseball meant that the Chicago Cubs were serious. It meant that this ownership wasn’t afraid to spend money. It meant that players wanted to be here and trusted in the process. It meant that the Cubs were on the cusp of winning a title.
Theo is leaving Jed with some clear headaches. Contracts colliding while having to decide on whether the team is going to compete during this closing window. Some of the guys that were traded away were young, talented baseball players that’ll have a bright future outside of Chicago and will most likely haunt fans for a long time. But at the end of the day, flags fly forever. And Theo Epstein will never have to buy a beer in the city of Chicago ever again.
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