Over the next several weeks, the Boston media, after largely ignoring the issue during the season, began to focus on Epstein's future. Even as the New England Patriots geared up for a run at their third straight Super Bowl title, Boston's sports pages and airwaves were dominated by debates concerning Epstein and his contract and endless speculation about the possibility of a rift between Epstein and Lucchino. For the first time, the new-era, feel good Red Sox were being compared to the dysfunctional clubs of old. "Epstein is young, smart, and 31-- and he isn't signed yet?" asked the Herald's Tony Massarotti. "How in the name of John Harrington does that happen, particularly to an organization that has otherwise taken so many strides in the last 3 1/2 years? Not so long ago, the Red Sox front office was perceived as being badly out of touch... [T]o be in this position, now, reminds all of the old days."
As the press coverage intensified during these final weeks of October, Epstein's salary demands were leaked to the media. Even as Epstein considered the leaks further evidence he couldn't trust certain people in the organization, Henry, who'd first learned of Epstein's salary request through a newspaper report, found himself angry with his general manager. Epstein was asking to be the highest-paid GM in the game, double what most other general mangers were making. Henry, who'd talked often with Epstein about their determination to accurately read the market, was confused. "How can that be the market?" Henry asked. One of the ways Henry deals with his displeasure is by simply ignoring a person. "Theo and I had been very close," says Henry. "But when money became the issue, we basically stopped communicating. At that point, I was mainly on Larry's side."
Despite Epstein and Lucchino's strained relationship and despite John Henry's newfound anger, Epstein and the Red Sox began to inch slowly toward an agreement. By late October, the main stumbling block seemed to be Epstein's bitterness over the continual leaks about the negotiations. Early in the week of October 24, Epstein, while turning down a three-year offer worth $1.2 million annually, gave Henry, Werner, and Lucchino what he considered his bottom line: He wouldn't come back for less than $1.5 million a year. By Thursday, October 27, Epstein and the team had come to terms for precisely that amount. "We pretty much had a deal," says Henry. "All of the [outstanding] issues had been laid to rest," says Henry, "except these ongoing leak issues." But instead of signing the deal before the end of the week, Lucchino recommended they wait until Monday, October 31, the last day Epstein was still under contract. Henry was confused. "I said, 'Why are you pushing it back to Monday?'" Henry says. "And Larry said, 'To give him three extra days to think about it. It's a big decision.' I wasn't in favor of waiting, but I said fine."
Epstein did think about it, and by time he woke up on the morning of Sunday, October 30, he was at peace with his decision. He would remain with the Boston Red Sox. He'd reconciled himself to a lack of privacy for as long as he stayed in the job. He'd promised John Henry he would no longer isolate himself in the baseball operations basement fortress, and now, after more than a year of resenting and blaming Lucchino, he realized he shared responsibility for their damaged relationship.
Then he got a phone call alerting him to an article in that day's newspaper. On the front page of the Globe's sports section was a Dan Shaughnessy column entitled, "Let's iron out some of the dirty laundry." When Epstein began reading, he felt his stomach drop. After weeks during which he'd talked with Henry, Werner, and Lucchino about his unease about the organization, here was confirmation of his worst fears. In his column, Shaughnessy, who'd known Lucchino and Charles Steinberg since the 1980s, when all three men worked in Baltimore, chided and belittled Epstein for not properly respecting his superiors. After all, Shaughnessy wrote, it was Lucchino and Steinberg who'd "discovered" Epstein and "held his hand" during his first years in baseball. Now, Shaughnessy wrote, Epstein was exhibiting an "alarming… need to distance himself from those who helped him rise to his position of power." Epstein, according to Shaughnessy, didn't even know all that much about baseball. "[I]t's a mistake to say [Epstein] knows more about baseball than Lucchino or anyone else in the Red Sox baseball operation," he wrote. Lucchino, after all, "was a good high school baseball player" and started working in the game "as an executive... when Theo was 5 years old." Finally, Shaughnessy gave Lucchino credit for "fall[ing] on" Epsteins's sword by taking the blame for the aborted Larry Bigbie trade with the Colorado Rockies -- presumably because Epstein was too much of a coward to do so himself -- and implied that Epstein had recently been spurring Peter Gammons into "trashing the Sox CEO."
Either Lucchino or Steinberg, Epstein felt sure, had prompted the column. The two men were, after all, the heroes of the piece, and both had said lines almost identical to some Shaughnessy had used.* Where else could Shaughnessy have gotten the incorrect notion -- repeated in the column as fact, without any attribution -- that Epstein had asked Lucchino to shoulder the blame for the Bigbie trade?** It was actually Henry and Epstein who had decided to nix the deal; Lucchino had never been a part of the conversation.
After reading Shaughnessy's column, Epstein sat down and wrote John Henry an email. The next day, Epstein wrote, he would resign as general manager of the Boston Red Sox. "I have a huge pit in my stomach," Epstein wrote. "But it's nowhere near as big a pit as I'd have if I'd already signed a contract."
"I love baseball," Epstein said two weeks earlier while discussing his future plans. "It dominates my life because I'm a part of it so much. But the big picture is, there's so much fucking more out there. You become such a prisoner of the game, because there's 162 games...The best thing [any baseball executive] might be able to do is, in between teams, take a year and do other things. That might be the single most valuable thing you can do." Now, Epstein would have just that opportunity.
*About a week earlier, several sources confirm that Charles Steinberg had a conversation with Dan Shaughnessy and another reporter in which he said many of the things that ended up in Shaughnessy's column. Steinberg says he never "spoke ill against Theo." "Nor would I," he says, "because that's inconsistent with how I've felt about him all these years, and I still know with the grace of God he's destined for more greatness."
**Over the next several months, Dan Shaughnessy repeatedly insisted that neither Lucchino nor his allies within the organization had urged him to write his October 30 column. But, on November 1, Shaughnessy wrote that the version of the Bigbie trade he wrote as fact was "the version held by Lucchino's camp (three sources)." Wherever he got the information, it simply wasn't true. "I vetoed the trade,"

