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Everybody Wants Their Own Theo Epstein

Boston’s hero and Chicago’s presumed savior is no longer a market inefficiency

Ringer illustration
Ringer illustration

In the Internet Age, monoculture is unachievable. But there remain a few things that we can all agree on. The Ringer is looking at this rarefied group all week. These are our Undeniables.

On June 17, 2003, Michael Lewis’s Moneyball hit bookshelves, and it changed the way the average fan looks at baseball. The book ultimately became a crossover sensation, influencing the business world and, perhaps more impressively, turning Jonah Hill into an Academy Award nominee. It called into question baseball’s tactical and statistical conventions in a way that, with all due respect to the ongoing work of Bill James, no mass market publication ever had. It spawned an eponymous revolution in the management and discussion of the game, and even though that revolution has undergone schisms of its own as it’s become the new orthodoxy, Moneyball is baseball’s decisive historical turning point of the 21st century.

It also shifted the focus of baseball in a way that’s altered our understanding of the game. For the first time, the hero was not the player, but the executive. And even though Billy Beane was the hero of Moneyball, he’s not the archetypal general manager of the Moneyball movement. No, it’s the guy the Red Sox hired when they couldn’t get Beane.

When Boston hired Theo Epstein on November 25, 2002, it changed the game forever, both figuratively and literally. Boston had finished second to the Yankees in the AL East for five straight years, despite making big, headline-grabbing moves for Pedro Martínez, Manny Ramírez, and lastly Johnny Damon, whose departure from Oakland precipitated the events of Moneyball itself. Unlike the 2002 A’s, Boston wasn’t an experimental group of castoffs on a shoestring budget; it was Old Money, a rich, well-scrutinized organization that would ordinarily have been run conservatively. Instead, team president Larry Lucchino handed the reins to the youngest general manager in MLB history. A 28-year-old lawyer with no playing or coaching experience, Epstein looked like he’d gotten lost on the way to a high school mock trial competition, and he showed up with big ideas and a mountain of quantitative data.

Epstein got to work immediately, signing Ramiro Mendoza, Mike Timlin, Bill Mueller, and David Ortiz, all either castoffs or veteran afterthoughts. He claimed Bronson Arroyo off waivers and bought Kevin Millar from the Marlins. In just a few weeks, he picked up a huge chunk of the team that would win the 2004 World Series for next to nothing. One of his first major moves was to attempt to replace the traditional closer with a closer-by-committee approach, a move that was misunderstood, derided, and eventually abandoned. But in Epstein’s first year in charge, the Red Sox led the major leagues in the Moneyball holy grails of on-base and slugging percentages.

After the Red Sox crashed out in the 2003 ALCS in crushing fashion, Epstein replaced manager Grady Little with former Phillies skipper Terry Francona, then made some more straightforward moves, trading for perennial All-Star Curt Schilling and signing closer Keith Foulke. He continued to tinker throughout the 2004 season, culminating in a four-way trade in July that brought in shortstop Orlando Cabrera and first baseman Doug Mientkiewicz at the cost of Nomar Garciaparra, who’d been the face of the franchise before Epstein’s arrival.

You know the rest: the comeback against the Yankees, the sweep of St. Louis and a broken 86-year-old curse, Epstein’s shocking resignation a year later when he dodged reporters by wearing a gorilla suit out of Fenway Park. It was Michael Jordan’s first retirement, for the Moneyball era. Then came the (ultimately false) rumors that he’d been following Pearl Jam around South America, followed by reconciliation between Epstein and the team, the Daisuke Matsuzaka signing, and a second title in 2007.

Epstein started out as an unconventional general manager, a neophyte swimming against the current. In 2011, he left Boston having diverted the river.

Take a look at the current crop of big league GMs. You’ll see a lot of younger faces, most of them white, young, and almost comically at ease in a button-down shirt and chinos.

When Epstein started in Boston, he was breaking into a rank of executives dominated by ex-players like Beane and ex-scouts like Seattle’s (and then Philadelphia’s) Pat Gillick. Today, they’re all like Epstein.

Of the 30 MLB GMs, 26 got their first GM jobs after Epstein did. Of those, 23 are 50 or younger, and 12 are 40 or younger. Only seven played professional baseball at any level. And only two, Seattle’s Jerry Dipoto and Arizona’s Dave Stewart, played in the big leagues.

The reason GMs all look like investment bankers now is that a lot of them probably would be investment bankers if they hadn’t gone into baseball. Some of the game’s top executives actually used to be investment bankers, including Dodgers president of baseball operations Andrew Friedman (the Batman to Epstein’s Superman) and Reds GM Dick Williams.

Practically, what the shift to the Epstein model of GM has done is replace the previous old boys’ club of ex-players and scouts with a new old boys’ club of well-connected star students from business school.

Of the 26 GMs hired after Epstein took over the Red Sox, 12 have Ivy League degrees, while most of the rest attended elite private schools like Wake Forest, Notre Dame, and MIT. Only eight current GMs — Stewart, Dipoto, Williams, St. Louis’s John Mozeliak, Kansas City’s Dayton Moore, Minnesota’s Terry Ryan, the Angels’ Billy Eppler, and San Francisco’s Bobby Evans — don’t have a degree from a private university, and Williams, who attended the University of Virginia, is the son of Reds chairman Joe Williams.

In February 2004, the Yale-educated Epstein described his entrance into baseball as “the sort of horseshit Ivy League connection that you’re supposed to feel guilty about — and I sometimes do.” His first job was an internship for Lucchino’s Baltimore Orioles, and Lucchino eventually took Epstein with him to San Diego and then Boston.

Still, Epstein, though sabermetrically inclined at the start, wasn’t a banker or an economist or a data analyst. He worked for San Diego’s public relations before moving over to baseball ops. Among his contemporaries, Epstein’s baseball résumé resembles Friedman’s or Houston’s Jeff Luhnow’s far less than it does that of Ed Wade, the much-maligned former Phillies and Astros GM.

The skeptic might say that Epstein took over a Red Sox team that already had Martínez and Ramírez, used its massive payroll to smooth out the edges, and won two World Series in four years. But that’s not giving enough credit to the forces beyond our control: He’s the guy who broke The Curse.

It’s therefore appropriate that when Epstein finally quit the Red Sox for good, it was for the only bigger fish in baseball’s metaphysical ocean: the Chicago Cubs’ 108-year title drought.

Once again, he’s taken a club with a huge payroll and turned it into the best team in baseball. His Cubs have a single playoff-series victory to their credit, and yet instead of holding our breath and wondering how and when the other shoe is going to drop, much of the baseball-watching public views a Cubs World Series title as something of a fait accompli. No other top-tier baseball executive — not Beane, not the Yankees’ Brian Cashman, not Mozeliak — could inspire that feeling of confidence.

Epstein was young and smart and Ivy League–educated, but that isn’t enough to run a successful front office. There’s still something inimitable about him.

More than a decade after it started, the search for the Next Cursebreaker has revolutionized front-office thinking and set up new classist barriers to entry in GM hiring. It’s even changed the structure of a typical front office. When Epstein signed on to be the Cubs’ president with Jed Hoyer as GM, it inspired copycats and title bloat across the league. But it’s failed to produce another Epstein.

So what sets him apart from all the imitators?

In his book The Arm, Jeff Passan recounts Chicago’s courtship of free-agent left-hander Jon Lester, starting with an anecdote about Epstein and Hoyer hammering out a deal in a San Diego hotel room with Lester’s agents and a bottle of Jägermeister.

“Almost everybody in baseball likes Epstein and his disarming sense of humor, his eternal pragmatism, and his appeal to both the intuitive and analytical sides of the game,” Passan writes. “He’s the guy who could sit at lunch one day with the jocks, the next day with the nerds, and not only look comfortable in both places but own the table.”

A top-level executive, like a GM or team president, needs to be able to manage both jocks and nerds, and in Chicago, Epstein has assembled a team of subordinates that includes people from both camps. As baseball has become more complex and scientific, executives no longer succeed or fail by their merits as evaluators or negotiators alone. It’s about developing trust with scouts and analysts — and indeed, with coaches and players as well — and that’s allowed Epstein to develop a network of talented and trusted lieutenants, from Hoyer to Joe Maddon, in Chicago.

Epstein’s approach to player evaluation and acquisition hasn’t changed that much since he was in Boston — he still has a knack for knowing when to move on from foundational players, from Garciaparra to Ramírez to Jeff Samardzija most recently. And he still values on-base percentage, as evidenced by the signing of Mueller and the drafting of Kyle Schwarber.

He has, for lack of a better word, a process, and that clarity of vision allows an executive to better communicate his goals and expectations to his subordinates. But Epstein has also shown an ability to adapt within that vision, and avoid mistakes made by other process-oriented GMs who failed to realize that ideological purity, when taken too far, can be a fatal flaw.

In 2003, Epstein tried to do away with the traditional one-inning closer, an experiment that failed so spectacularly it scared front offices even more analytically inclined than Boston’s out of trying it. So Epstein abandoned it and signed Foulke, who’d led the AL in saves the year before. When Lester wanted more money from Chicago than Epstein’s budget would allow, he blew up his budget. When the Cubs had no positions for Schwarber or Addison Russell, they made positions. When Dexter Fowler was available for peanuts but the Cubs already had too many outfielders, Epstein signed him anyway.

Of course, a large part of Epstein’s success comes from the fact that he’s had better tools to work with: brand-name teams with near-unlimited budgets in both Boston and Chicago, franchises owned by deep-pocketed people with the patience and willingness to stand by rebuilding projects that could get unpopular very quickly if they went bad. An executive’s ability to construct a winning plan is only as good as ownership’s willingness to fund it and to tolerate bumps in the road. Epstein got that in both Boston and Chicago, but he might not have elsewhere.

Epstein’s success might not be replicable because it’s born out of a unique combination of ability, personality, and being in the right place at the right time. But there’s something else, too.

When Moneyball came out, many (perhaps even most) people drew the wrong lesson. The 2002 Oakland A’s won by valuing statistics and selling out for on-base percentage, but those were means to an end, not the end itself. In the years after Moneyball came out, OBP became as expensive on the free-agent market as batting average or pitcher wins had been a decade before. And while their competitors chased innovations from five years ago, the A’s changed tack and moved on to the next innovation. Moneyball isn’t about sabermetrics, but about finding market inefficiencies.

This demonstrates the folly of looking for the next game-changing visionary executive in the exact same place the last one came from. So, if there’s a lesson to learn from the legend of Theo Epstein, it’s this: The next Theo Epstein isn’t going to look like Theo Epstein.