I used to follow people home. I just like being anonymous so much that I would follow people home because they didn't know who I was, and I could watch them. I know how that sounds. I could not exist but observe.
Theo Epstein
I believe in the First Amendment. But I also believe we should be mindful of how other people feel.
Whoever your boss is, or your bosses are, they have 20 percent of their job that they just don't like.
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.
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.
There are a lot of ways to make a positive impact on the community without necessarily being a politician.
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.
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.
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.
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.
You can't go through life thinking about what could go wrong.
We've made plenty of mistakes. But the ones that we've hit on, we've gotten lucky with some impact guys back, some best-case scenarios as far as how the guys have turned out.
When we build that foundation for sustained success, and it ultimately results in a World Series, it's going to be more than just a World Series.
I work for the Chicago Cubs, a team with a following so loyal and adoring and a history so forlorn that we were known nationwide as the Loveable Losers.
The only time I think about my contract is when I'm asked about it by the media.
Baseball is better with tradition, with history. Baseball is better with fans who care.
If I let my brain follow its path unfettered, it would be kinda ugly.
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.
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.
I think everyone deserves more than one World Series every 108 years so.
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.
Having a relentless lineup full of professional hitters works on so many levels. It works in terms of pure baseball reasons: if you get on base, you're going to score runs.
It took me coming to the Midwest to realize I was the jerk. People are so nice here. They're so grounded.
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.
The leadoff-hitter thing, I think, it's always nice to have an established leadoff hitter and to have someone who can really get on base and set the tone.
This game will make you cry more often than not.
Typically, it takes young players years to adjust to life in the big leagues and to start performing up to their capabilities. Most of the blame for this rests on these ridiculous old baseball norms that say young players are to be seen and not heard.
There are certainly times when baseball is much more than bread and circus, times when baseball resonates deeply and meaningfully with many, many people, and times when a game that is built around overcoming failure can teach us all a few important lessons.
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.
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.
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.
The Red Sox hadn't won in 86 years when we took over. We didn't run from that challenge - we embraced it.
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.
I still wake up thinking about draft choices we should have made that would have impacted the franchise for a long time, but I don't wake up thinking about one individual player move.
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.
We knew the 2017-18 offseason would be one of our most challenging. We've known that for a long time.
I think people want the Cubs to succeed, and by extension, they want people associated with the Cubs to succeed.
I don't think I'm a chameleon. I can feel where people are coming from, what makes them tick, where they are vulnerable, what makes them feel good about themselves. I get just as much out of it as they do. I love connecting.
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.
As I sat back and imagined what my transition from the Red Sox might be, I thought it would smell more like champagne than beer, I guess you would say.
If we think a playoff spot's not in the cards, there will be no concern for appearances or cosmetics whatsoever. We'll continue to address our future and trade off some pieces that would keep us respectable.
You've just got to kind of play the hand you're dealt.
If you want to continue to be good and perform at a high level and be deep in all areas, you still have to hit on some undervalued players, too. You can't just go out and sign marquee free agents or trade for players when they're at the peak of their value. That's not a formula for long-term success.
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.
To win the World Series, you have to be able to do a lot of things well.
Failure is inherent in the game. So if you don't respond well to adversity, you're probably not going to have a long career.
I don't want to be buried in a Red Sox casket.
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.
Players that tend to respond to adversity the right way and triumph in the end are players with strong character. If you have enough guys like that in the clubhouse, you have an edge on the other team.
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.' At some point later, when someone wants information and you want to draw the line, how do you do that?
