And that brings us to the Winter Meetings, which get underway Monday at Walt Disney World Swan & Dolphin Resort in Lake Buena Vista, Fla. Baseball's annual gathering will give Epstein and Co. a chance to possibly fill some of the gaps on the roster.
Next week, you'll hear Jeff Samardzija's name a lot. The right-hander has been the subject of trade rumors since July with teams such as the D-backs, Nationals and Blue Jays coveting the hard-throwing starter who is coming off his first 200-innings, 200-strikeout season.
Samardzija, 28, and the Cubs have talked about a long-term contract, but the pitcher, who will be a free agent after the 2015 season, is apparently gambling that it's better to wait. Look at pitchers such as Phil Hughes, 27, who got a three-year, $24 million deal from the Twins, and you'll understand why.
The Cubs do want to add pitching, and Epstein said the emphasis is on "quality" arms. The Cubs have traded 40 percent of their rotation the last two seasons but Epstein said they are not looking for free agents whom they can sign and then flip at the Trade Deadline.
"Every starting pitcher we acquire is someone we hope is starting Game 1 of the World Series for us," Epstein said.
Epstein didn't specify when that would be.
If Samardzija stays with the Cubs, he'll join Edwin Jackson, Travis Wood and Jake Arrieta in the rotation. The Cubs did plan to talk to Scott Baker, but he also was exploring other options.
The Cubs also are in the market for a closer. After Carlos Marmol struggled and was then traded, and Kyuji Fujikawa was injured, Kevin Gregg stepped in and totaled 30 saves for the third time in his career. Gregg, 35, is now a free agent and shopping around.
"We have guys who could close," Epstein said, "but I think that's an opportunity for us. If you go to market with the closer's role ready to bestow on somebody, that can help you sign a pretty good pitcher and can help your club. ... We're going to hit the market with a full closing opportunity to offer to the right pitcher we acquire, either through free agency or a trade, and know we have some interesting options in house."
One possibility is right-hander Hector Rondon, who was acquired last year in the Rule 5 Draft. The Cubs have selected pitchers in each of the last two years -- Lendy Castillo was the 2012 selection -- and could add someone again during the Draft on Dec. 12, which closes the Winter Meetings.
There are other needs, which may become clearer once Epstein and Co. spend more time with new manager Rick Renteria to see if there's anything specific he wants on the roster. Renteria, who underwent hip surgery after the regular season ended, was expected in Chicago late this week for his first visit since being named manager Nov. 6.
Last year, the Cubs got a head start by signing free-agent pitchers Baker and Scott Feldman, catchers Dioner Navarro and J.C. Boscan, and outfielder Brian Bogusevic before the Meetings got underway. Of that group, only Bogusevic is expected back for 2014. Feldman was dealt at last year's non-waiver Trade Deadline, Baker spent the season rehabbing from Tommy John surgery and is a free agent, Navarro recently signed a two-year, $8 million deal with the Blue Jays, and Boscan signed with the Dodgers.
So far this offseason, the Cubs have signed outfielder Ryan Sweeney to a two-year, $3.5 million contract, and traded for backup catcher George Kottaras. They've also signed some players to Minor League contracts, including outfielders Aaron Cunningham and Casper Wells, infielders Walter Ibarra and Chris Valaika, catcher Eli Whiteside, and pitchers Paolo Espino and Carlos Pimentel.
No offense to any of them, but those aren't the players Cubs fans are giddy over. Bryant teased by winning MVP honors in the Arizona Fall League, but he'll open in the Minor Leagues in 2014. The Cubs will be looking at Mike Olt and Luis Valbuena at third base. Epstein has been clear about what the young players in the system need to do to advance.
"One thing we tell our players, and I tell them this directly, and [general manager] Jed [Hoyer] tells them this directly at the player development program is, 'You want to move up? ... Dominate your competition,'" Epstein said. "It comes down ultimately to performance."
Unfortunately for the Cubs, the baseball season won't wait for their top prospects to develop.
During a presentation to season-ticket holders in early November, the top prospects were introduced via video and Wrigley Field's 100th anniversary was emphasized. The renovation plans for the ballpark were delayed while the Cubs try to reach an agreement with rooftop owners. That means no video scoreboard, which would have generated more revenue.
Epstein has a tight budget.
"Our business plan and our facilities plan and our baseball plan are all a couple years away from reaching fruition," Epstein said. "We're going to be as aggressive as we can given our situation. We clearly need to get better but we're not going to do anything at the expense of an increasingly exciting future."
The Cubs, who have lost 197 games over the last two seasons, are in the market for some good deals.