Theo Epstein: Curse Slayer

Many tried, but only one reigned supreme... twice.

To paraphrase: Theo’s a god, and we are not, and I just thought I’d let us know.

If ever there was a lock for the Hall of Fame, with all due respect to Mariano Rivera and his first-ballot unanimous selection, it is Theo Epstein. As you doubtlessly already know, he has stepped down from his position with the Chicago Cubs, the place where his legacy is cemented in… well, cement. Carved in stone. Etched into the annals of time.

For those of you playing at home, that is already one Vertical Horizon reference and the perfectly proper use of the word annals [applause break].

I’m not sure this is even a controversial take; he took two teams with World Series Championship droughts of over 150 years combined and delivered the goods in both Boston and Chicago; two of the most storied baseball towns in the country. Nay, world. Nay, universe! As an unapologetic Red Sox fan, I was sad to see him move on from Boston, and when he landed with the Cubs I audibly said, “If he wins the Cubs a World Series, he’s a Hall of Famer, no doubt.” Nobody can vouch for this, of course, because I was by myself at the time. It may, however, stir your pot a little to hear that nobody else enshrined in Cooperstown will be as deserving of the honor. So, in recognition of the greatest GM / President of Baseball Operations / Front Office Prodigy Genius who has ever graced the game of baseball, here’s some stuff about the man himself.


Five Facts About Theo


1. Theo Epstein was 28 years old when he took over as General Manager for the Boston Red Sox on November 25, 2002, setting the MLB record for being the youngest GM ever. Two years later The Red Sox celebrated their first World Series win in 86 years.

2. He has a twin brother who is one minute older than him, making Theo what I can only imagine is the most annoying little brother in the history of hugely successful little brothers.

3. He is a guitar player and participates regularly in events called “Hot Stove Cool Music” each year to benefit charity. Just before the 2015 event, Theo said, “We’ve collectively raised more than $6 million and look forward to increasing that total this year through another great night of music, baseball and giving back.” It is now up to nearly $12 million. The money, in part, supports his own charity but also funds organizations like the Jimmy Fund and Dana-Farber Cancer Institute whose mission includes, “…using its discoveries to improve the treatment of adults and children with cancer.” The relationship between the Red Sox and The Jimmy Fund dates back to 1953.

4. The name of his charity is the “Foundation to Be Named Later” which only underscores his brilliance. Think of a better name for a big-time charity founded by the greatest GM in baseball history, I’ll wait… No, I won’t, because you can’t and I have things to do. According to their website, it is, “…an organization to raise funds and awareness for nonprofit agencies serving urban youth and families…” Among others, the foundation benefits the Peter Gammons Scholarship that supports, “…Boston and Chicago area high school students… Without [which], these students would not be able to attend college.” A full list of beneficiaries of FTBNL can be found here.

5. His grandfather and great uncle, brothers despite the confusing way we label our elders and forebears, wrote the movie Casablanca. In a way, it makes perfect sense: Babe Ruth was sold to finance the Broadway show, “No, No, Nanette” which opened in Boston’s Globe Theatre on Sep 16, 1925, thereby placing the Curse of the Bambino on the Beantown Ballers only to be broken by the descendant of writers of one of the most iconic films ever made. “Here’s looking at you, kid.” Kid? Goat? Well, Theo broke that curse too!


Four Legends


There are a lot of acts that have come through the “Hot Stove, Cool Music” events. Founded by Peter Gammons and Jeff Horrigan, a former Boston Herald writer, in 2000, the concert series eventually partnered with Theo’s Foundation to Be Named Later to benefit the Jimmy Fund. After moving to Chicago, Theo took his show on the road and the concerts followed. The 20th Anniversary edition took place on June 25, 2020, with the Cubs. It was done virtually, of course, because, Corona. But the show did go on. Here are four legends* who have been a part of it along the way. It’s good to be Theo.

1. Steven Tyler, Aerosmith. You don’t need me to tell you how big this guy’s mouth is, but it’s HUGE. His Boston roots run deep and he is no stranger to charitable work. According to cbsnews.com, Steven opened his, “first Janie’s House in Atlanta in 2017,” a home to support abused girls. A second home, “…is located at Youth Villages in Bartlett, Tennessee.” The organization is named after the Aerosmith hit, Janie’s Got a Gun, a song about a girl suffering unknowing horror at the hands of her own family.

2. James Taylor. Five-time Grammy award winner and Rock and Roll Hall of Fame inductee. He’s seen fire. He’s seen rain. He’s seen Bronson Arroyo shred on the guitar. Also, you know, the sunny days that he thought would never end. A Boston Red Sox fan with a special place in his heart for Fenway Park launched a 2017 tour of ballparks all across the country. In 2015, he also penned Angels of Fenway, a song recognizing the emotions that ran deep in 2004 after they won the World Series for the first time in 86 years. The song begins, “’86 summers gone by, Bambino put a hex on the Bean, We were living on a tear and a sigh, In the shadow of the Bronx machine.” That’s the hex Theo helped to break. Of course, he broke another in Chicago 12 years later. Side note: my father passed away at 53 and had he lived to 54 he would have seen his beloved Sox win it all. The emotions of all that? Taylor nailed it.

3. Bernie Williams. Music legend who once played baseball for a time with a club called the New York Yankees. You may have heard of it. It’s not fair that he could be so good at baseball and guitar, but he is and you’re just going to have to come to terms with it.

4. Nada Surf. What can I say about this band that hasn’t already been said by many regional and local newspapers that have since gone out of business? Who can forget the hits like “Popular” and also… “Popular” … and the undeniably catchy “Popular.

*honorable mentions: Eddie Vedder, the Smashing Pumpkins, Liz Phair, and Cheap Trick (Forbes.com)


Three Quotes


Baseball is a game based on adversity. It’s a game that’s going to test you repeatedly. It’s going to find your weaknesses and vulnerabilities and force you to adjust. That adversity, in the big picture, is a really good thing because it shows you where your weaknesses are. It gives you the opportunity to improve.

Theo Epstein, Cubs Press Conference, 05/11/17


This is real talk about baseball that is also real-talk about life. Put that in your pipe and smoke it. Or don’t, smoking is really bad for you. Maybe just contemplate it for a minute and find some inspiration from a little #truthbomb. Not everything is going to be a home run; sometimes, today, it’s a walk or a strikeout instead.


There are certainly times when baseball is much more than bread and circus, times when baseball resonates deeply and meaningfully with many, many people, and times when a game that is built around overcoming failure can teach us all a few important lessons.

Theo Epstein, 2017 Yale Graduation Commencement Speech


If I had a nickel for every time I’ve heard the ol’ “bread and circus” gag… I’d have no nickels because I have never heard that before in my life. Alas, there is no questioning what Theo has done to give back to the communities through his ongoing charitable works. It also shows his humility, or at the very least, that he knows he should feign humility. He’s an example of getting to the top with a tremendous work ethic and a willingness to admit his own shortcomings and fix them, not stubbornly double down on foolishness. We could use more of that in, well, everything.


It is the greatest game in the world but there are some threats to it because of the way the game is evolving…using analytics and other measures to optimize individual and team performance have unwittingly had, you know, a negative impact on the aesthetic value.

Theo Epstein, Resignation Press Conference, 11/18/20


This mea culpa is shocking but in a good way. Sure, it comes after he got his from doing the very thing that he is saying he maybe should not have done, but let’s not quibble over what some might consider a tiny bit of hypocrisy here: he was part of a baseball revolution that has swept the sport, gripped fantasy players and fueled an entire baseball adjacent industry. He leveraged it into three World Series titles with two organizations that had gone so long without one they were both “cursed” and people really believed in dark magic. He was given a target and he hit the bullseye but is here acknowledging that a three true outcomes game may not be quite as interesting to the casual baseball fan and taking responsibility for being part of that. C’mon, accountability in the year 2020?! That deserves an award all unto itself.


Two Awards


Theo has been recognized in many ways with honors and awards, but when magazines do it, it really means something. I mean, right? MAGAZINES!

1. Fortune Magazine ranked Epstein #1 in their 2017 list of the “World’s Greatest Leaders.” According to their own article about their own award winner that they wrote themselves, Theo “…responded to his placement on the list with a selflessness that epitomizes one of the exact traits that makes a leader great.” Who are we to argue with Fortune Magazine’s conversation with itself?

2. In April 2017, Time Magazine named Epstein one of the world’s 100 most influential people. Time says, “His vision helped end historic World Series droughts in both Chicago and Boston.” Truly amazing. Truly remarkable. Truly inspiring.  The article also states that “Theo Epstein’s got that weird hue around him” which they never really go on to explain and hopefully didn’t get pulled from an online dating profile. Fun fact: the article itself is written by well-known Cubs fan, John Cusack. In the article Cusack talks about why Theo deserved to be included: “His vision helped end historic World Series droughts in both Chicago and Boston. But his power lies in a paradox, in the knowledge that the only way to keep power is to give it away.” As Eric Chesterton said on April 20, 2017 in an article on MLB.com, “Two curses broken; two recognitions of his ability. One wonders what is next for Epstein.” Same, Eric. Same.


One Conclusion


You don’t get to jam with Steven Tyler, be recognized by Time magazine, or become the youngest GM in the history of the game by being a slouch. We all know Theo is amazing. You can hate the Sox or the Cubbies and still know you want that guy in your team’s front office. But it goes way beyond normal degrees of awesomeness; he is at another level.

Not only will he be in the HOF, but they should make a life-sized wax replica that greets visitors at the door (once we are allowed to visit things like doors again). Maybe it should be animatronic like Disney’s Hall of Presidents except it’s just Theo showing off his three World Series rings.

Once it goes down, he will be THE MOST DESERVING person in the entire institution and you can “@’ me all you want, it won’t change the truth of the matter. Maybe also shame me with some retweets. I’d really hate that.

Maybe he’s getting out of baseball at exactly the right time? Maybe he will land with another team. Maybe he should become the next and possibly greatest Commissioner of Major League Baseball. Who knows? I mean, he probably knows. One thing is for certain though: He’s everything you want, he’s everything you need, he’s everything inside of you that you wish you could be.

He says all the right things.

At exactly the right times.


Photo by ShellyS, licensed under CC BY-NC-SA 2.0 | Adapted by Quincey Dong (IG: @threerundong)

Matt Goodwin

Husband. Dad. Teacher. Writer. Podcaster. Baseball Fan. Quippy. Makes up words. FSWA. IBWAA.

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