Three years ago, Epstein's contract negotiations became uncomfortably public, as one news outlet reported an extension was done only for the GM to resign from his post the next day. But Epstein was able to work out his conflicts with upper management and was back on the job three months later.
Now, it seems that Epstein -- who grew up just a couple of miles from Fenway Park -- couldn't be any happier with his situation.
"When you sit back and think about being a general manager, this is exactly the type of organization you'd want to work for," Epstein said. "Great fans, great ownership and a tremendous foundation of our scouting and player development, which if we don't screw it up will lead to long-term success. We're all in this game to work with good people and to try and win a World Series."
The Red Sox, under Epstein's guidance, have won two of the past five World Series after an 86-year drought.
Epstein became the youngest general manager in Major League Baseball history when the Red Sox gave him the job in November 2002 at the age of 28.
At the time, Epstein vowed to turn the Red Sox into a "scouting and player development machine."
In short order, that's exactly what occurred. Under Epstein's watch, the Red Sox have drafted and developed solid players like Dustin Pedroia, Jonathan Papelbon, Jacoby Ellsbury and Justin Masterson. Epstein was assistant GM when the Red Sox drafted Jon Lester in 2002, and the lefty had a breakout season in 2008.
Only once in Epstein's first six seasons as GM have the Red Sox failed to make the postseason. That occurred in 2006.
His club won the 2004 World Series after trailing the arch-rival Yankees, 3-0, in the American League Championship Series, and becoming the first team in MLB history to come back from such a deficit to win a best-of-seven series. They went on to sweep the Cardinals in the World Series.
In 2007, the Red Sox again came back in the ALCS, this time from a 3-1 deficit, to defeat the Indians in seven games. They then swept the Rockies in the World Series.
This year, dealing with a barrage of injuries, they almost pulled off another miracle.
The Red Sox trailed, 3-1, in the ALCS against the Rays, and were behind 7-0 in the seventh inning of Game 5 at Fenway Park before scoring eight times in the final three innings to win that game and then knot the series by winning Game 6 at Tropicana Field. But Tampa Bay won Game 7, 3-1, denying the Red Sox a chance to become baseball's first repeat champions since the 1998-2000 Yankees won three in a row.
Epstein, 34, began his MLB career in the Padres organization.