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Chicago Cubs: Theo Epstein is MLB’s best executive after World Series win


Some used to call him the “Boy Genius” and “Boy Wonder” for how young he was as a baseball executive.

After Wednesday night, Theo Epstein can add another nickname to the many he’s been given; “the Ender of Curses.”

At age 28, he was given the keys to the Boston Red Sox in 2004 as their general manager and helped build a World Series team that ended an 86-year drought by winning the World Series in his very first season in 2004. He then proceeded to win another World Series just three years later in 2007 and solidified himself as an icon in Boston similar to Red Auerbach with the Boston Celtics.

Then after seven years with Boston, Epstein decided to leave Boston and took his talents to the Windy City and took over as the president of baseball operations for the Chicago Cubs and went to work on trying to end another championship drought.

It took him a few years of remaking the roster with young talent and making smart trades that helped shape the future of the franchise. Epstein then brought over one of the best managers in the game in Joe Maddon before the 2015 season.

Maddon nearly won the World Series in 2008 with a very young Tampa Bay Rays team and was looking to win one in Chicago alongside Epstein, who would build him a championship-caliber roster.

Epstein got close in 2015 (and nearly made the Back to the Future prediction come true) when they made it to the NLCS, but were swept by the New York Mets. One year later, the Cubs went out and spent money on key free agents, made a trade for a dominating reliever and by season’s end, had the best record in all of baseball and found themselves in the Fall Classic for the first time in 71 years.

And then in dramatic fashion, just like Epstein’s 2004 Red Sox team had to do in overcoming the odds. The Cubs rallied from a 3-1 deficit against the Cleveland Indians and knocked off the Tribe to claim their first World Series crown in 108 years and giving Epstein his third championship in his 14 years as an executive.

Epstein’s construction of the Cubs over the course of the last five years has been extremely well done. He got Anthony Rizzo, Addison Russell, Kyle Hendricks, and Jake Arrieta in trades from re-building deals, signed Jon Lester, John Lackey, Dexter Fowler, Jason Heyward, David Ross and now World Series MVP Ben Zobrist in free agency.  Plus he made a deal with the New York Yankees to land Aroldis Chapman at the deadline to solidify the back-end of the bullpen and drafted Kris Bryant three years ago with a first round pick.

Add that mixture of a roster to go along with Maddon’s wisdom and fresh and calm demeanor of a baseball leader and you have a recipe for success and in 2016, Epstein’s creation was on full display.

And now at 42 years old, Epstein has solidified himself as the very best baseball executive right now. If we want to look at things, Epstein may very well be the best executive in all of sports right now, as few have been able to do what he’s done in his sport: three championships and ended an 86-year and 108-year championship drought.

If Epstein wanted to call it a career right now, he would easily be a lock for the National Baseball Hall of Fame. When he’s all set and done as a baseball executive, they may name a wing in Cooperstown if he’s able to add more championships and records to his resume to go along with the work he’s put in over the last 15 years.

But considering just how good the Cubs are right now, Epstein’s likely going to watch his Cubs contend and compete for a few more championships while he’s in Chicago and likely has no plans to leave anytime soon.

While there are a lot of solid executives in baseball right now; Brian Sabean, Brian Cashman, John Mozeliak to name a few, Epstein has solidified himself as the very best in Major League Baseball. As long as he wants to continue to run baseball organizations, he will continue to be considered the golden standard of what you want in the architect of your baseball team and franchise.


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Robert D. Cobb
Founder, Publisher and CEO of INSCMagazine. Works have appeared and featured in places such as Forbes, Huffington Post, ESPN and NBC Sports to name a few. Follow me on Twitter at @RobCobb_INSC, email me at [email protected]