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" The Cubs - with their passionate fans, dedicated ownership, tradition, and World Series drought - represented the ultimate new challenge and the one team I could imagine working for after such a fulfilling Red Sox experience. "

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" It's a natural push and pull that exists in any sports organization. When you are in a big market and then you win, and you're up against the Yankees, and ratings are what they are and attendance is what it is, no one wants to go backwards; as a business, you don't want to go backwards. "

Theo Epstein

You

Business

Win

" Something as simple as transparency is really scalable because it quickly impacts the culture. And the culture is something everyone feels. If upper management is really transparent with everyone, that has this amplifying effect. Then you tend to attract players who operate that way, on the same wavelength, and coaches and fans. "

" It stinks to give up a good player. But if you think that way, you'll never make any trades. You have to focus on what you're getting back. "

" It's a human phenomenon that there has to be a reason for everything. There almost never is. "

" Scouting and player development is the key to year-in and year-out success, not the occasional lucky hit. There are no definitive answers in this game, no shortcuts. When you think you've got it all figured out, you can get humbled very quickly. "

" Failure happens to everyone in this game. It's not something worth harping on. What is worth focusing on is how you respond to that failure. "

" We want to try and transform the Red Sox into a team like the Braves or the Yankees, where you can almost count on the postseason every year. "

" No one is immune to needing to sit or needing to go down at the right time, and you want to give guys a chance. "

" Baseball is a game based on adversity. It's a game that's going to test you repeatedly. It's going to find your weaknesses and vulnerabilities and force you to adjust. That adversity, in the big picture, is a really good thing because it shows you where your weaknesses are. It gives you the opportunity to improve. "

" Communication is different in the clubhouse than it is in a boardroom. The heartbeat that exists in the clubhouse, you don't find that same type of heartbeat in the front office. "

" I do think we can be honest and upfront that certain organizations haven't gotten the job done. That's the approach we took in Boston. We identified certain things that we hadn't been doing well, that might have gotten in the way of a World Series, and eradicated them. "

" I ended up staying 10 years in Boston. It was nine as GM but 10 years there. That seemed about right: long enough to try to make a difference and try to contribute to winning teams and some championships. "

" The goals is to create a really high 'floor' for this organization, where the 'off' years are years where you might win in the high-80s and sneak a division or a wild card or win 90 games and get in and find a way to win in October. And the great years, you win 103 and win the whole thing. "

" I love being in a city that's playing October baseball, where you can just feel everyone captivated by the ball club, everyone walking around tired from staying up late, prioritizing baseball above all else. It's a great phenomenon. "

" There has to be active, hands-on management in concert with the manager to lead the organization and make sure that the standards that we set for the organization as a whole are being lived up to. "

" You have years where most things go your way, and you have years where more things than usual seem like a challenge. "

Theo Epstein

Challenge

" If we can't find the next technological breakthrough, well, maybe we can be better than anyone else with how we treat our players and how we connect with players and the relationships we develop and how we put them in positions to succeed. "

" Tolerance is important, especially in a democracy. The ability to have honest conversations, even if you come from a different place, a difference perspective, is fundamentally important. "

" The Cubs, we built one of best farm systems - I think for a while there, it was the best farm system in baseball. And that was great. It got a lot of attention. But we didn't want the credit for the farm system. What we wanted was to see if we could do the tricky part, which was turn a lauded farm system into a World Series champion. "

" I like to have some privacy, especially where my family is concerned, so when I'm recognized, I'll usually say something like 'I get that all the time' or 'Theo Epstein? Who's that?' "

Theo Epstein

Privacy

Say

" You can't go through life thinking about what could go wrong. "

Theo Epstein

Life

Thinking

" I'm not going to try to deny that I'm a Red Sox fan. I grew up a Red Sox fan, had a great decade here that I really enjoyed, and that will always be a part of me. "

" I don't know if I could go to another run-of-the-mill baseball department and work because it would probably feel like work. In Boston and Chicago, it doesn't feel like work. It feels like a privilege. "

" When people do things they weren't even sure they were capable of, I think it comes back to connection. Connection with teammates. Connection with organization. Feeling like they belong in the environment. I think it's a human need - the need to feel connected. "

" Whoever your boss is, or your bosses are, they have 20 percent of their job that they just don't like. "

" If multiple starting pitchers underperform at the same time, it's always going to leave you in a stretch where it's hard to play better than .500 baseball. "

" I chose my classes based on which professors did not take attendance, and then I traded Padres tickets for notes from class. I wasn't the student of the month. "

" The 'Chicago Sun-Times,' I remember, ran a full-page, front-page photo-shop of me walking on water across Lake Michigan, as if by showing up I was going to miraculously fix the team's fortunes. Imagine their disappointment, then, when I announced a long-term rebuilding plan focused on acquiring young players and winning in five years. "

" Bostonians vs. Chicagoans, they have different sensibilities, and I can only say this because I consider myself a Bostonian. You know, the Puritanical roots in Boston - the 'sky is falling' mentality a little bit. We could be on a great run, and we'd lose one game, and everyone's panicking. "

" There's a cumulative effort within the course of a game, a series, and a season, too, where you see so many pitches and have so many at-bats that you can wear down an opponent. Once you develop that reputation as a club, year after year, players come in, and they tend to fit in with that profile. "