By Phil Rogers

SAN DIEGO -- From the window in his hotel suite, Theo Epstein could see Pacific Beach, the neighborhood where he lived when he was starting his baseball career, as an assistant in the Padres' public relations department.

He was a recent Yale graduate who had decided to follow his passion, not earn the highest paycheck available. "It was a good place to be 21,'' Epstein said Wednesday evening, after another spectacular sunset.

He's older now, for sure, but still on the roll that started with the bet he made on himself in those days. With the Winter Meetings ending on Thursday, he'll return to Chicago with his Cubs in a good place, thanks to deals he and his staff sealed in 36 eventful hours.

Epstein landed the top two targets on his pitching list, with Jon Lester agreeing to a six-year, $155-million contract shortly after Jason Hammel signed a two-year, $20-million deal, and for good measure traded two entry-level pitching prospects for All-Star catcher Miguel Montero.

A 50-to-1 shot to win the 2015 World Series when the Hot Stove season began, the Cubs have cut their odds to 12-to-1, according to Bovada. But don't be misled.

The hiring of Joe Maddon and signing of Lester isn't an indication that Cubs Chairman Tom Ricketts is moving all his chips into the middle of the table to try to make the magic happen next season. Epstein still sees himself in the middle of a building project, not at the end of one.

"It's all about long-term thinking,'' Epstein said. "People ask if we're all in for '15. I think the best response is we're all in for the future, and the future starts in '15. [Next season] is important. We're going to do some things to put as competitive of a roster as possible on the field, and try to win. Our goal is to win our division and -- [quick laugh by Epstein] -- as Joe said, win the World Series. But we're aware of what we're growing.''

There's business left to be done, just as there were always press releases to be written when Epstein first set up shop here. Among the items left on the Cubs' to-do list:

1. Add more experience to a young roster.

Maddon says that Lester will "rub off'' on the other pitchers. Montero is a player with standing, as well, and Anthony Rizzo and Starlin Castro have mileage beyond their years, but on many days Maddon's lineup will feature four or five players who are rookies or in their first seasons. The Cubs are working to sign two or three veteran role players, with Jonny Gomes and David Ross prominent on that list.

"There are a number of really good veteran players out there who could make a profound impact on the clubhouse, the culture around the team, younger teammates,'' Epstein said. "We'll look at all of them.''

2. Keep close tabs on Javier Baez's work in Puerto Rico.

While the Cubs insist that the kid with the ferocious swing will be their second baseman when they meet the Cardinals in the season opener, that's not set in stone. Baez is down to play about six weeks of winter ball after hitting .169 with 95 strikeouts in 52 games as a rookie. For now, those numbers define him as much as the 69 home runs he hit the last two years. If he doesn't make improvements this winter, the Cubs should be covered with Tommy La Stella (acquired in a trade with Atlanta) as their second baseman.

3. Take phone calls from other teams looking to acquire players from the Cubs' inventory.

Welington Castillo, the No. 1 catcher before the Montero trade, almost certainly will be traded if Ross is signed to catch Lester, as he did in Boston. Luis Valbuena and outfielder Justin Ruggiano are of interest to teams looking to add infield depth. But the Cubs' biggest area of surplus is the rotation, as they now control 10 pitchers who combined to start 181 games last year. Left-hander Travis Wood, an All-Star in 2013, could fit elsewhere. Edwin Jackson? Available, although the Cubs do hope that he'll click under Maddon, as he did with Tampa Bay.

"I think we have a ton of starting pitching depth, which is great,'' Epstein said. "You need it. You need nine, 10 starters to get through the season. Some of those guys could end up in the bullpen. We're protected against Spring Training injuries and setbacks. We'll see how that develops. But there's so much pitching out there on the free agent market and the trade market right now, I don't think any of our guys are necessarily in high demand. That's fine with us because we love our depth, but maybe [we'll trade pitching] later in the winter if we get approached.''

4. Explore a long-term contract with Jake Arrieta.

He's under control for three years, so there's no urgency. He's also represented by Scott Boras, which usually means he will be difficult to sign for his free-agent years. But the big right-hander has been solid in most of his 34 starts for the Cubs and was solid as the No. 1 guy after Jeff Samardzija was traded last July. It could be impossible to sign him long-term a year from now.

Boras said Wednesday he expects to discuss Arrieta's situation in January and February, when they prepare for a possible arbitration case.

5. Avoid the urge to make another splash.

The best thing the Cubs have going for them is the overwhelming inventory of players they have accumulated, but there's no reason to start dealing from that strength. The time to deal shortstop Starlin Castro is probably next winter, even if that means that Addison Russell spends a full season at Triple-A. Or he might yield a very nice return next July, as Samardzija, Matt Garza and Ryan Dempster have in previous Julys.

"We haven't given up any of our most significant prospects in these deals, haven't given up a draft pick in any of these deals,'' Epstein said. "We've preserved our future. That's something that's always going to be important for us because we're trying to build toward a long run, where we can have success year in and year out, and we're not going to sacrifice that even as we look to maximize our '15 roster.''


Phil Rogers is a contributor to Sports on Earth and a columnist for He previously wrote for the Chicago Tribune and the Dallas Morning News.