The Cubs Way

by Tom Verducci

  In January 2002, Lucchino, with Steinberg in tow, left the Padres to join Henry and Tom Werner as the new owners of the Red Sox. Two months later Boston hired Epstein as an assistant to the interim general manager, Mike Port, whom ownership had installed as a placeholder after letting go of general manager Dan Duquette. Epstein was hired just two weeks after director of player development Ben Cherington hired Jed Hoyer, who, like Epstein, had just turned 28 years old, to work in the scouting department. Hoyer had played baseball at Wesleyan University, where Epstein’s twin, Paul, matriculated and played soccer with one of Hoyer’s roommates.

  The first time Hoyer met Theo was when the Red Sox played an exhibition game in Houston just prior to Opening Day 2002. Already there was a sense that Epstein was on a fast track under the new Boston ownership.

  “We hit it off right away,” Hoyer said. “We were basically exactly the same age. Both of us were working all night, every night. It was pretty easy to connect. I remember everyone trying to curry favor with him. When he was brought onboard, his hiring was a big deal. He was a rising star in the game, and the Red Sox were able to bring the hometown kid back home. I tried to stay away at first. Like I said, I felt everyone was running up to him to curry favor. Then one night we were going to some event and it was just the two of us taking the subway. We hit it off on that ride. He started to find a lot of work for me.

  “It was a pretty bare-bones operation then. People from the Duquette regime had been let go. It was a small shop. Theo, even as an assistant general manager, tried to build that up.”

  During that summer of 2002, Epstein heard that Billy Beane, the Oakland general manager, was cooperating with writer Michael Lewis on a book that would use the Athletics as an example of how the statistical revolution was changing baseball. The book would be titled Moneyball: The Art of Winning an Unfair Game. Epstein and Beane had become friends, based largely on their shared passion for leveraging advanced analytics. Epstein wasn’t happy, however, when he heard about the book project. Said one Red Sox insider then, “I remember Theo being annoyed. He said, ‘I can’t believe Billy is letting him write this book. He’s going to give everybody the same idea. He’s handing out the blueprint.’ After that, every owner in baseball read the book and said to his baseball people, ‘Do this.’ At the time at least 20 of the 30 teams still looked at stats crookedly.”

  The Red Sox were on the same cutting edge of analytics as Oakland, only they were more circumspect about it. Said Hoyer, “There were times in 2002 when I went to bed thinking Billy was my boss.”

  While Beane was cooperating with Lewis, Epstein went to Henry with an idea: “Why don’t we hire Bill James?” Epstein had long admired James’s work, so why not have the sabermetric guru produce exclusive work for the Red Sox? Henry loved the idea. After all, like Epstein, Henry had been reading James’s Baseball Abstract since the mid-’80s, and he had built his fortune in the commodities trading business by relying on cold, hard data to drive his funds.

  Henry convinced James to work for the Red Sox. The hiring was announced on November 5, 2002, but by then James already had produced his first project for the club.

  “I have this vivid memory of being in the upstairs office,” Hoyer said, “right after we hired Bill and getting his first piece of work. It came in a FedEx package and we just tore this thing open. We couldn’t wait to read it. We both grew up reading the Abstract, and now we were sitting in a room with Bill’s exclusive work.”

  The spiral-bound project ran 86 pages, much of it devoted to James’s exclusive ratings of the upcoming free agent class as well as the historical benefit of having left-handed hitters populate the Boston lineup, a counterintuitive thought because the nearness of Fenway Park’s Green Monster in leftfield invites an emphasis on right-handed pull hitters.

  Meanwhile, Lucchino drew up a document listing the top 10 qualifications of the ideal general manager. The second qualification he listed was “familiarity with, and willingness to use, modern quantitative approaches in evaluating players, in addition to traditional methods.” Shortly after Henry, Werner, and Lucchino announced the hiring of James, they offered the general manager position to Beane with a five-year contract worth $12.5 million. Beane took the job, slept on it, and then changed his mind. On second thought, he did not want to leave California. He told the Red Sox owners they should hire Epstein.

  The owners then turned to Toronto general manager J. P. Ricciardi, a Massachusetts native who had worked under Beane in Oakland before taking the job with the Blue Jays. Ricciardi declined to leave. He told the owners they should hire Epstein. Ricciardi’s endorsement was another testament to how quickly Epstein made an impact around baseball, especially among forward-thinking organizations.

  Finally, on November 25, 2002, the Red Sox made Epstein, one month shy of his 29th birthday, the youngest general manager in history.

  What happened next was an immediate mushrooming of intellect and energy. Epstein and his group of top baseball operations advisors—many of them young and statistically savvy, including Jed Hoyer, Ben Cherington, Josh Byrnes, and later Jason McLeod—set about upgrading a Boston team that in 2002 missed the postseason with 93 wins and scored the second-most runs in the American League, trailing only the Yankees. They saw a roster that gave too many at-bats to players who were not very good at getting on base, such as Tony Clark, Rey Sanchez, José Offerman, Carlos Baerga, and Shea Hillenbrand.

  “In September of 2002, Theo started talking to [James],” Hoyer said. “Theo started pushing your thinking in different directions. It became a completely different puzzle. What Theo does better than anyone is he wants as much scouting stuff and background stuff and makeup information as anyone. He believes in never having enough information and asking for more. It’s probably his best quality. It’s not about focusing on any one area, because if you do that you may miss the biggest piece of information. Listen, you’re still going to miss. And you can be overly cautious to avoid missing, and he’s not. He’s as aggressive as it gets.”

  Epstein and his baseball operations people set about fishing in free agent waters in that 2002–2003 off-season. James’s exclusive free agent ratings system was the equivalent of a fish-finder device. And as they fished, the Red Sox crew looked around them and happily noticed something: few teams were fishing in the same waters.

  “It was amazing,” Hoyer said. “There was just a lot of favorable talent out there. And we were hitting on guys like Bill Mueller, Kevin Millar, and David Ortiz. I remember we were all over Travis Hafner, and we weren’t able to get a deal done…Carlos Guillén, Erubiel Durazo…there were a lot of guys who were freely available that were very talented. That was a group of players that was really undervalued. We were thinking, We can keep acquiring these guys as much as we can. That winter of ’02–’03 led to much of the success to come in ’03 and ’07.”

  Epstein added infielders Mueller, Millar, and Ortiz, as well as second baseman Todd Walker, first baseman Jeremy Giambi, and pitchers Mike Timlin and Bronson Arroyo. Those seven players cost him only three nonprospects from his minor league system and $13 million in salary toward his 2003 payroll.

  “We had a really frantic off-season,” Hoyer said. “Looking back on those years there was so much energy and change. That first off-season may have been Theo’s finest work. It was a really fun time. We were all around our early 30s and working nonstop. It felt like we never took a break, never had lives outside of work. We stayed at work.”

  —

  They did take one fortuitous break one day in July 2003, while the team was on the road against Tampa Bay. Epstein was sitting at his Fenway Park desk when his secretary told him, “George Webb from Pearl Jam is on the phone.”

  Webb, the band’s equipment manager, had heard that Epstein considered Pearl Jam his favorite band. Webb arranged for tickets to the concert in Mansfield, Massachusetts, for Epstein and his own “band,” the whiz kids in his baseball operations office, including Hoyer, Peter Woodfork
, and Amiel Sawdaye. They watched from the side of the stage. At one point Eddie Vedder threw Epstein a tambourine. After the show, Epstein told Webb that he and the band could take batting practice the next morning on the field at Fenway Park. So excited was Vedder, a Cubs fan who grew up in Evanston, Illinois, that he went to sleep with his glove near the nightstand. Alas, he did not get to sleep until after some all-night libations with the Buzzcocks, Pearl Jam’s warm-up band. Vedder slept through the Fenway fun.

  The next night Epstein and his Red Sox crew returned to Mansfield for the second show. Vedder played the first encore wearing a Red Sox cap. After the show, meeting him for the first time, Epstein could not resist needling Vedder about sleeping through the chance to hit at Fenway.

  “Friends ever since,” Epstein said.

  Something else about Vedder, besides his thoughtful, piercing music, appealed to Epstein. He met Vedder at the same age Vedder had been in 1994, when his reaction to enormous fame—the release of a third platinum-selling album just months after he appeared on the cover of Time—was akin to treating a wildfire: you had to tamp down the beast, not stoke it. The band refused, for instance, to produce music videos. Building an image creates expectations of what a person should be, and those expectations, and the falseness of them, Vedder told Melody Maker that year, “just start tearing you apart.”

  Epstein shared the same ethos as Vedder. Upon being named Boston GM, Epstein had turned down offers to appear on The Tonight Show with Jay Leno and three morning network news shows.

  “It felt wrong at that point,” Epstein said. “I would have been on as a reward for being a young GM—a novelty, a gimmick. Even though it was appealing on the face of it, I felt it was wrong. I passed on all that.

  “It really is the players’ accomplishment. Not that I’ve been perfect in that regard, but once you thrust yourself out there in the public domain, it’s really hard to retreat, to say no or reclaim that certain part of your life as private. It’s hypocritical to say when things are going well, ‘Interview me. Ask me how great I am. Ask me about family and personal life,’ and, at some point later, when someone wants information and you want to draw the line, how do you draw the line?”

  —

  Under their first-year general manager, the 2003 Red Sox pushed the Yankees all the way to the 11th inning of the seventh game of the American League Championship Series, only to see Aaron Boone, with his home run off Tim Wakefield, join Bucky Dent and Bill Buckner in the deep catalog of Red Sox villainy.

  It has been said about the Beatles that their happiness was never so great as it was in the moments just before the boys from Liverpool first hit it big. If so, spring training of 2004 was the height of happiness for Epstein and his young bucks in the front office. Eight of them joined in renting a house in Cape Coral, Florida, about 20 minutes from Boston’s training complex in Fort Myers. Under one roof were Epstein, then 30; Hoyer, 30; Cherington, 29; Woodfork, 27; Sawdaye, 26; Craig Shipley, 40; Galen Carr, 28; and Brian O’Halloran, 32. The house went by the unofficial name Phi Signa Playa. There were laptops everywhere, and pizza, beer, and poker to fill the few hours of downtime.

  “We had such a great time,” Hoyer said. “It was a huge house, and everyone would work different shifts. Some guys would leave super early and get back late. Other guys would leave late. We all carpooled in the mornings. We heard ‘Seven Nation Army’ by the White Stripes all spring in that car.”

  Sports Illustrated asked Epstein to cooperate for a story, with the guys posing around the house for a kind of team picture. He declined.

  “We haven’t accomplished anything yet,” Epstein explained.

  “That’s the beauty of Theo right there,” Hoyer said. “He would never allow something like that, even now. After we won the World Series [on Wednesday, November 2, 2016] we were right back to work doing something Saturday and Sunday right before the GM meetings. You don’t see him touring different shows. That’s the players’ place. So it doesn’t surprise me he said that back in ’04. No one had camera phones back then, so it’s lost to history.”

  In 2004, in his second season as general manager, Epstein won the World Series, unleashing a catharsis across New England the depths of which had been unknown in baseball history. It was in the wake of such emotional outpouring that the idea of someday running the Chicago Cubs first occurred to Epstein, even if it occurred to him in a fleeting manner.

  “As far back as the aftermath of the ’04 World Series I would talk about it with my friends a little bit,” Epstein said. “ ‘If I ever move on, the Cubs would be the one spot because it was so powerful to win in Boston.’ The whole aspect of the job was seeing how much it resonated with people and families. You never let go of that. It adds meaning to the whole thing. I would joke around with friends—I remember telling Jed after ’04—but it was also sort of a pipe dream, because I was focused on Boston.”

  Being a Beatle is hard work. Epstein discovered that quickly. The Red Sox won 95 games in 2005, but were swept in the Division Series by the Chicago White Sox. It was viewed as a disappointing year. A weary Epstein, rather than sign a renewal of his contract, resigned on Halloween, famously avoiding the media by slipping away from Fenway Park in a gorilla suit.

  Epstein would return to the Red Sox a few months later, before the next season, and win the World Series again in 2007, and come within one win of another pennant in 2008. In six seasons from 2003 to 2008, Epstein’s Red Sox won two World Series titles and twice came within one win of playing for more. The expectations of running at peak capacity never eased. In 2009, as they did in 2005, the Red Sox won 95 games but were swept in the Division Series, the kind of seasons that in Boston began to get relegated to the “failure” bin.

  In 2010, Epstein, sensing that the years of pushing for 95 wins or more were starting to take their toll on the Boston player development system, made a subdued plea for some perspective. He mentioned that while the Red Sox were still trying to win, the team might be wise to consider 2010 a “bridge” season, in which the organization continued to build for the future, rather than pushing the chips all-in on a year-to-year basis. The sentiment did not go over well inside or outside the front office walls, not with the vast sums the Red Sox were paying their players and not with what the Red Sox were asking their fans to pay to watch them.

  “But we were just—and this is a fight that goes back to when I first took the job and even when we won—we were just getting too big,” Epstein said. “When we won, our fan base grew, our revenues grew, the expectations to keep creating revenues grew, our expectations of winning 95 games and getting deep into playoffs grew every year and it reached a point…One eye-opener is when we tried to have a little bit of a longer-term plan one year and I remember trying to be transparent with the fan base and saying, ‘This is probably going to be a bridge year. We’re going to try to compete but also get a little bit younger and some of our prospects will need one more year to mature and we’re really looking forward to 2011.’ It didn’t go over too well internally or externally. The internal part was a little disappointing because I thought we were acting in our best interest—long-term interests and medium-term interests.”

  The environment around him had changed. And so, too, had Epstein.

  “I sort of began to react to things emotionally that I shouldn’t have,” he said.

  In that summer of 2010 Epstein attended the funeral of a Red Sox employee. The funeral pamphlet included a Red Sox logo. So did the casket. It shook him to see a man go to his grave so deeply associated with the team.

  “I remember thinking, ‘I really don’t want this to be me,’ ” he said. “Because, when you’re not unconditionally in love with a place anymore, I think you resent to a certain extent the degree to which you’re identified with that place, or you self-identify with that place.

  “So I just began to internally distance myself from it a little bit emotionally. I don’t want to be buried in a Red Sox casket, and how long do I h
ave to stay here until it’s who I am? That’s not really logical thinking. It’s emotional thinking. Probably because of the pressure and the mistakes I made because I didn’t do a good enough job taking care of my own environment.

  “And it was the cumulative effect of taking the job at 28 and dealing with it for nine years, internalizing a lot of it, living season to season, game to game, and then seeing when you try to calm things and plan for the long term there’s sort of a visceral, negative reaction. It doesn’t leave you in a real stable [place]…It’s hard to find a real stable safe haven to exist with that, unless you create it yourself, and I didn’t do a good enough job of doing that.”

  The Red Sox won 89 games in 2010 and missed the playoffs for only the second time in eight seasons. Now the pressure really turned up to get Boston back into the postseason. Epstein’s answer was to trade three prospects, including 21-year-old first baseman Anthony Rizzo, to San Diego to get veteran first baseman Adrian Gonzalez, with a seven-year, $154 million extension to Gonzalez tacked on after the deal was completed. Epstein also was close to trading for veteran outfielder Carlos Beltran from the Mets, who was entering the last year of his contract. The proposed deal would have come at a minimal cost: two fringe prospects, including pitcher Michael Bowden. But Epstein walked away from the deal when medical reports gave him concern about the stability of Beltran’s knee.

  Needing another bat, Epstein wrote a $142 million check to free agent outfielder Carl Crawford for the next seven years. Crawford became one of the worst big-ticket signings in Boston history.