Theo Epstein reflects on Cubs' incredible ride and hopes for October

MILWAUKEE -- Dressed in a navy sport coat and a plaid, button-down shirt, Cubs president Theo Epstein was anything but inconspicuous as he stood behind the 100-level section during Sunday’s regular-season finale.

No matter what he says, no matter how good Jake Arrieta or Kris Bryant or Anthony Rizzo are, no matter how many Binny’s commercials Joe Maddon makes, Epstein is still the face of the Cubs.

This team is his baby. Now, like a proud father, Epstein has to watch the Cubs walk on their own.

As we talked midway through the Cubs’ 3-1 win over the Brewers, Cubs fans stopped for pictures (Epstein obliged) or just took them from a distance like amateur paparazzi. Even two Brewers fans, dressed in head-to-toe gear, wanted a picture with Epstein.

“We take them all,” Epstein said.

Most fans just wanted to thank him. The Cubs are a franchise built on hopes and dreams with the expectation that every season will be unlike the others and that providence smiles on us all -- eventually.

Epstein has been through postseasons both historic and heartbreaking. Some have ended in a snap. Others have lingered for years, replaying over and over.

As the Cubs prepare for a one-game, winner-take-all playoff game against the Pirates on Wednesday, what is scratching at Epstein when he goes to bed and when he wakes up?

“Unfulfilled hopes,” he said. “In October, you have a special team, and you want to see a special run. There’s such an arbitrary nature to it sometimes. A ball bouncing a certain way or a bleeder down the line or something. You want to see teams get what they deserve. I think our guys deserve a lot.”

This is truly a special team, an unselfish but competitive mix of young studs and reliable veterans. Everyone figured Bryant would come up and mash, but no one outside the organization realized Kyle Schwarber would contribute so much. When Starlin Castro was benched, who thought he'd come back and be Mr. September?

"This team all year had that little bit of magic, and they’ve had a special feeling in the clubhouse," Epstein said.

After a 97-win dream season, the Cubs are headed to Pittsburgh on a 5 p.m. flight Monday. If the Cubs can beat the Pirates -- with Cy Young contender Jake Arrieta on the hill, they certainly have a fantastic shot -- then who knows how far they can take this ride?

We've been waiting for this day since August when we realized the Cubs were legit. Now it's almost here, and you want this feeling of expectation to last forever.

On Sunday, Epstein and his general manager, Jed Hoyer, watched a handful of innings in the seats a dozen rows up from home plate. Then they retreated to the clubhouse to watch TV. By the time the media met with Maddon after the game, the two were in his office watching the Pirates win their 98th game on the mounted TV.

So much of the Cubs' narrative since Epstein was hired in late 2011 has been about his building the franchise -- what moves he could make, what players he could draft. But now he’s stuck watching and cursing just like the rest of us. If the Cubs win, Epstein and the front office will stay busy doing some advance scouting, looking at little things here and there to help Maddon find an edge in matchups. But mostly, he’ll watch and worry.

“Honestly, we’re just observing -- what some people would say we do 365 days a year,” he said. “You just sit back and watch in October.”

How does Epstein watch games in the postseason?

“On the road, in the stands. At home, in the suite,” he said.

No, not literally, Theo. How does someone with so much invested manage to watch the game when every pitch is crucial?

“Employing every defensive mechanism known to man,” he said. “You process it, you’re on the edge of your seat for every pitch. There’s a lot of adrenaline going, and then years later you look back and you’re like, ‘I don’t remember a thing.’ You have to go watch the video. I think when something is out of your control like that, you do sort of defend yourself a little bit.

“In October, it’s an odd feeling to be a nonparticipant in something you’re so invested in. During the regular season, you start counting outs. Maybe, ‘Hey, we need seven more outs. Let’s figure out how are we going to script that.’ You start doing that with 15 outs in the postseason games. Everything’s amplified.”

Although the Cubs haven’t hit Pirates starter Gerrit Cole much this season, Arrieta is on the mound Wednesday, and Epstein likes his chances to be nervous for more than one game. The Cubs are 48-33 on the road this year, just short of the franchise record of 49 wins set in 1945. They are 6-4 at PNC Park this season.

“It’s a good feeling to have a guy like that,” he said. “The players all really believe in Jake -- not just his talent, but who he is as a person. They know he’ll show up big time, and they want to go out and score some runs for him.”

Talking to Epstein on Oct. 4 gave me the chance to reminisce about past Octobers. Past is prologue and all that.

I brought up Oct. 1, 2012, when I went to Wrigley for the Cubs' 100th loss in a 101-loss season. Jason Berken was the Cubs' starter. Dave Sappelt batted second.

Epstein pivoted to Oct. 1, 2013, when he met with the media after firing manager Dale Sveum.

“I remember the questions in that press conference were so negative, so negative,” he said. “And meanwhile, we felt great about what was going on because we knew how talented the young players were and how much the organization had turned around, as far as infrastructure and talent. But it hadn’t manifested at the big leagues. I remember stopping at one point and saying, ‘Look guys, you might look at this as a failure right now, but I can tell you outside this organization, outside this city, people are saying the Cubs are going to be really f---ing good pretty soon.' And we are.”

Pretty good, indeed.

While he was thinking in expletives back then, what he actually said was, “I can tell you, and you don't have to take my word on it, outside the organization, outside the city, the story is the Cubs are coming fast, and the Cubs are coming strong. That's the reality. When you take a step back and assess the talent in the organization, that's accurate."

In 2013, not even Epstein knew the Cubs would be able to land Maddon or sign Jon Lester. A lot of things had to go right for this organization to win 97 games this season. No one could script it or plan it. What we witnessed this season was the magic that makes you care about a team like you put it together yourself.

For the guy who did just that, you can believe this is what he envisioned.

“You have to believe before you see it,” Epstein said. “That’s been an important concept with our organization building and this year with our big league team. I think we were pretty confident that we were going to get there. We were going to have a real core and sustainable success. But we didn’t know when. This was honestly the best-case scenario in terms of the timetable."

Next up is one game. On deck is a lifetime of potential memories.

“This team all year has that little bit of magic, and they’ve had a special feeling in the clubhouse,” Epstein said. “It feels like the type of team that deserves a real run here, and you just want to see them have that.”