Peter J. Kaplan
6 min readDec 2, 2020

THEO EPSTEIN

If he never spends another day in baseball, Theo Nathaniel Epstein has already punched his ticket to Cooperstown as a first ballot Hall of Fame inductee.

Not too shabby for the kid who was born in New York City and grew up in Brookline, MA.

His genes aren’t bad either.

His father is Leslie D. Epstein, an American educator, essayist and novelist, and currently Professor of English and the Creative Writing Program Director at Boston University.

A Guggenheim Fellowship for Creative Arts (US and Canada) honoree, Leslie’s father Philip and his uncle Julius — identical twins — (along with Howard Koch) were Academy Award-winning screenwriters, perhaps best remembered for their screenplay of the film Casablanca (1942).

Theo’s mother Ilene, co-owned a woman’s clothing boutique in Brookline’s Coolidge Corner enclave, The Studio, which she described as “the Cheers of Brookline.”

“We know your name. And that’s wonderful for our generation,” she added.

After 40 years in business, Ilene and her partners — one of whom was her identical twin sister — decided to close the doors last year.

“We did it our way and, for a very long time, very successfully,” Epstein continued. “And the impact that we made, apart from the clothing, on people’s lives is the most satisfying of all. How could you not take pleasure, enormous pleasure, in that?”

Blood lines like those give a young person a head start.

And the Epstein children — Theo, twin brother Paul, and sister Anya — were off and running.

Working from the back forward, Theo Epstein was the Chicago Cubs’ president of baseball operations for the past nine seasons, before stepping down on November 17.

He transformed the long-suffering Cubbies from a franchise mired deeply in losing, to a World Series champion in 2016, effectively eradicating 108 years of futility.

When Epstein made his announcement to explore other pursuits — while not ruling out a return to baseball sometime down the road — club Chairman Tom Ricketts admitted it was a “sad day for [him] personally,” and described Epstein as a “great partner and truly great friend.”

He embellished by saying, “Really I think the legacy that Theo leaves behind is an organization that expects to win, not an organization that is surprised to win.”

Theo Epstein, now almost 47, led his hometown Boston Red Sox to two World Series championships in 2004 — killing an 86-year curse, the so-called “Curse of the Bambino” — and 2007.

With his Cubs’ victory in 2016, #3 for him, he would become one of five baseball executives to lead multiple organizations to titles, and became one of four to accomplish the feat with teams in each league, joining Pat Gillick, John Schuerholz and Dave Dombrowski.

Gillick and Schuerholz are in the Baseball Hall of Fame; Dombrowski is not yet eligible.

The Red Sox took a gamble when they made Theo Epstein the youngest general manager in baseball history at the age of 28, on November 25, 2002.

He promptly turned the organization into a scouting and player development machine, surrounding himself with analytics-driven contemporaries who knew and loved the game as much as he did.

He made some impactful acquisitions — see Curt Schilling and Keith Foulke, but also Kevin Millar and Bill Mueller — to dispose of the curse in 2004, and it was the wave of talent he had assembled in the depleted farm system which he inherited — including Dustin Pedroia, Jacoby Ellsbury, Jon Lester and Jonathan Papelbon, to name a few — that helped vault the club to the World Series title in 2007.

It certainly didn’t hurt to have Big Papi — with respect to Pedro — arguably, the greatest acquisition in the franchise’s rich and storied history.

Actually, Pedro putting in a good word to management about his fellow Dominican Republic native, didn’t hurt either.

Ortiz signed with the Red Sox in January 2003 after being released by the Minnesota Twins a month before.

The terms of the contract?

One year worth $1.25 million.

It was Epstein’s sagacity in turning down Ortiz’ request to be traded in early 2003, because he wanted more at-bats, which proved to be the game-changer.

Ortiz started only 32 of the first 61 games and was sitting behind a guy who was hitting about a buck-eighty (Jeremy Giambi).

Papi had swatted all of two HRs in the first two months of the season and after Epstein broke up the logjam of players ahead of him by trading Shea Hillenbrand, Ortiz hit 29 HRs in the second half.

And never looked back.

Nor did Theo.

Epstein was not afraid to be bold — goodbye Nomar — and the Sox made it to the ALCS four times in his nine seasons as GM, and qualified for the playoffs six times.

Lest we forget, in Epstein’s first season on the job — ’03 — the Red Sox were 5 outs away from reaching the World Series.

With no time to waste, on December 4, 2003, he then hired the man who would turn out to be the perfect manager for this band of “Cowboy/Idiots,” Terry Francona.

Francona’s four-year stint as the manager of the Philadelphia Phillies (1997–2000) was notable only in its mediocrity.

As the Phils’ skipper, the team never rose above third place in the NL East and his best finish was in 1999 when the club was 77–85.

He was fired following the 2000 campaign and closed the chapter in Philly with a 285–363 (.440) record on his resume.

Tito spent the following season as a special assistant to the general manager with Cleveland, and after that he served two one-year terms as a bench coach for Texas (2002) and then Oakland (2003).

The rest, as they say, is history and due to the alignment of the stars, Epstein’s innate savvy and feel, or all of that, his [Epstein’s] ability to spin gold was fast becoming the stuff of legend.

It has been speculated, as mentioned, that Theo Epstein will take some time away from the game for now.

He himself has said that one day he’d like to be part of an ownership group.

The NFL’s Jacksonville Jaguars were rumored to have him on their radar to fill their now-vacant GM position; they fired Dave Caldwell following Sunday’s loss to the Browns (November 29).

(This move, while a long-shot, is not unprecedented. The chief strategy officer for those very Browns is Paul DePodesta who previously served in the front offices of the Cleveland Indians, Oakland Athletics, San Diego Padres and New York Mets.

He was also the GM of the Los Angeles Dodgers for two years, named to the post at age 31, in 2004).

In the meantime, Rob Manfred is the tenth and current Commissioner of Major League Baseball.

Though approved unanimously to a five-year contract extension in 2018 which runs through 2024, the road especially lately, has been a rocky one.

Few, excepting the MLB owners for whom he works, think he’s very good at his job.

There are those who believe that he’s the worst commissioner in sports.

Some of his recent decision-making is open to question, and has become fodder for spirited debate.

To wit:

Opting not to punish any of the Houston Astros players for their roles in the cheating scandal that helped them win the 2017 World Series is at the top of the list;

Defending his position not to strip the franchise of its title and seeing no reason to take back the World Series trophy, which he referred to as nothing more than a “piece of metal,” is right up there;

His orchestration of baseball’s return during a pandemic — widely chastised — was shoddy and left a bad taste in the mouths of many, as he and the owners did whatever they could to portray the players as greedy and unwilling to sacrifice.

This besmirched the image, character and integrity of the game, and those who play it;

And finally, his handling of the Joe Kelly/Astros debacle — suspending Kelly for eight games in a truncated 60-game season, the equivalent of 22 games in a full 162-game campaign — for throwing at, but not hitting any batters, defies logic and seems to be the hallmark of someone who is starting to fly blind.

I suppose you know where this is going.

How about Theo Epstein as the next Commissioner of Baseball?

This piece was written by Mr. Kaplan in late-November/early-December 2020.]

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