CHICAGO -- It was the eye roll that changed Theo Epstein's career.
He's foggy on the timing, but it might have been 1997, Epstein's first full season working in baseball operations for the Padres. A Yale graduate who'd moved to San Diego to get a law degree before breaking into baseball, Epstein had so impressed GM Kevin Towers that Towers poached the young Epstein from the team's public relations office and brought him into baseball ops. From the sidelines during a conversation between Padres utility man Craig Shipley and some club officials, Epstein saw Shipley roll his eyes at something one of the men said.
"I kind of asked him, 'Where is that coming from?'" remembered Epstein, who two decades later is president of baseball operations for Cubs and one of the game's most recognizable executives. "He goes, 'Players are always skeptical of the front office.'"
"Because somewhere along the line," Shipley replied, "every player has been lied to."
That sentiment has stuck with Epstein ever since.
"From that point on, I always made it a point to be brutally honest," Epstein said over the weekend, as the Cubs prepared to meet the Mets in the National League Championship Series. On Tuesday, the series shifts to Chicago for the first NLCS games at Wrigley Field in a dozen years, starting with Game 3 (Air time 7:30 p.m. ET, game time 8 p.m. ET on TBS).
It's a mantra Epstein believes served him well as he moved from the Padres to the Red Sox, where became a 28-year-old general manager and built the team that snapped Boston's 86-year World Series championship drought, to the Cubs, where Epstein is in the midst of what he hopes is a similar revival.
Epstein won two World Series titles in Boston before Chicago hired him in October 2011 to lead a long-term rebuilding effort. The emphasis from the start was on "long-term;" during his tenure, Epstein has traded away established players like Marlon Byrd, Ryan Dempster, Matt Garza, Alfonso Soriano, Jason Hammel and Jeff Samardzija. One of Epstein's first trades sent hard-throwing pitcher Andrew Cashner to the Padres for two prospects including Anthony Rizzo. Epstein picked up Game 3 starter Kyle Hendricks from the Rangers for Dempster in 2012, and Jake Arrieta from the Orioles in '13. One of Epstein's last big "sell" trades sent Hammel and Samardzjia to the A's for a package that included Addison Russell.
The Cubs lost 101 games in Epstein's first season and drafted second overall the following year, selecting Kris Bryant. They lost 96 more games in 2013 and picked fourth the following year, getting Kyle Schwarber.
At the Major League level, these were painful years. But the Cubs' organizational talent grew.
"We asked our fans to go through a lot, and our whole goal was to be as transparent as possible," said Jed Hoyer, an old friend of Epstein's from Boston who became Cubs GM under Epstein.
"Theo had town hall meetings with our season ticketholders, and he got up there and told them what the plan was," Hoyer said. "There were some people who were critical, but we weren't going to 'hide the ball.' It was certainly Theo's leadership to say, 'Let's be clear and candid about what we're going to do,' because it is a bit unusual to do it in a bigger market, especially a market that's expecting you to go for a championship every year."
Epstein and Hoyer have known each other since 2002, when the Red Sox hired Epstein as assistant GM. On one of Epstein's first few days on the job, he and Hoyer, who already worked in Boston's front office and was a college friend of Epstein's brother, took the same train to an all-staff dinner. They meshed instantly, Hoyer said, and have remained close ever since.
"I trust him entirely," Hoyer said. "In this game, all you want to know is that a person's intentions are pure. When you have an arrangement like this [with Epstein as president and Hoyer as GM], that's the most important element."
How has Epstein changed since that train ride?
"He's probably the least-affected person by change I've ever known," Hoyer said. "He's the same person, a baseball junkie. He's just got more grey hair now."
Epstein strove to take the same honest approach to dealings with players. When he courted free agent Jon Lester last winter, Epstein was candid that the Cubs might need until 2016 or '17 to contend.
Others told similar stories.
"I know him from Boston. He's a straight shooter and honest, which I really appreciate," catcher David Ross said. "I got released by Cincinnati, and he was honest with me and told me what Cincinnati thought about me, and that hit home because I didn't see myself as that player or person. But it made me realize that you're always being watched, you're always being judged. So for me to sleep good at night, I needed to do everything I possibly could to make sure I was doing my job.
"That was probably a career-changer for me, to be honest with you. Those kinds of conversations, when you get guys that are making all the decisions to be honest with you, that's important."
Now, those painful seasons have yielded to a special one, and the promise of more to come.
"But nothing is promised in this game," Epstein said. "There are teams with these big, five-year windows, and they don't materialize, or they close quickly, or there are injuries, or bad decisions by people like me, or underperformance.
"There's nothing promised but today, and that's why we really want to make the most of this opportunity in October, even though we're also excited about our tomorrows."
Adam McCalvy is a reporter for MLB.com. Follow him on Twitter @AdamMcCalvy, like him on Facebook and listen to his podcast. This story was not subject to the approval of Major League Baseball or its clubs.