Theo Epstein Is Leading the Chicago Cubs' Franchise-Changing Offseason

The Chicago Cubs have embarked on what might be their most important offseason in franchise history, one that will start the team’s transformation from lovable loser to perennial World Series threat.

It starts now, and Theo Epstein will drive the push.

Epstein was hired as the team’s president three years ago. He had already broken the "Curse of the Bambino" in Boston, and the Cubs charged him with shattering their own "Curse of the Billy Goat." Having not won a World Series since 1908 or a National League pennant since 1945, the franchise is in Epstein’s hands, and he is now ready to pounce the team into contention. 

“We said we're going to be aggressive over the next 15 months and look for opportunities to get better,” Epstein said last week, according to Paul Sullivan of the Chicago Tribune. “It’s probably the first time agents can come into our suites without having to look both ways to make sure no one sees them coming in.

“We're no longer the runt of the litter, I guess.” 

The movement started last month. 

"

Theo Epstein the architect of lifting one curse took a huge step in destroying another with the #Cubs reported hiring of Joe Maddon as mgr.

— Linda Cohn (@lindacohn) October 29, 2014"

Epstein’s hiring of Joe Maddon was the first big step of the offseason, showing the rest of the game that the Cubs were no longer willing to sit idly back as they have the previous three offseasons, which all led to fifth-place finishes in the National League Central. Maddon is a respected manager and leader, and that he seemingly left the Tampa Bay Rays for the Cubs was a clear signal that Epstein, along with general manager Jed Hoyer, is ready to make a big impact in the trade and free-agency markets.

Soon after Maddon’s hiring, the rumors came hard and heavy. The Cubs were thought to be targeting several free-agent pitchers, eyeing another in a trade and willing to part with highly regarded position prospects.

And aside from Epstein shooting down the rumor that the Cubs could do something like sign Jon Lester and Max Scherzer, most of the rumors have been accurate. 

"

Theo Epstein on the Cubs signing two prime starters for $100 million-plus each: "That's not going to happen."

— Mike Vorkunov (@Mike_Vorkunov) November 12, 2014"

The money might be available to do it, but Epstein has long had convictions about not signing pitchers to long-term contracts and for more than $100 million, especially when they are on the wrong side of 30. Still, the prize might be too shiny this winter to pass up on them completely.

Epstein and Hoyer are supposed to meet with Lester this week with the hopes that their pitch will be enough to lure Lester, who is also considering his and Epstein’s former employers, the Red Sox. The Cubs see Lester as the stable post in their blueprint for immediate relevancy. With him anchoring their young, underrated rotation—the Cubs were second in the NL in pitching WAR (17.5) and third in starters’ WAR (13.1), according to FanGraphs—Chicago would have the kind of pitching staff that could contend in the NL Central.

With another quality starter, the Cubs would have the kind of rotation that could contend for a pennant.

Regardless of whether Lester works out for the Cubs, the team is also focusing on other arms. Philadelphia Phillies ace Cole Hamels has been on Epstein’s radar since August when the team claimed him from the waiver wire. A deal could not be struck in the days following the claim, but the Phillies are willing to make Hamels available for trade this offseason, and the Cubs have plenty of young talent to dangle and the money to absorb the remaining $90 million on Hamels' contract through 2018.

The Cubs have previously balked at trading some of their prospects, but attitudes are changing this offseason. Epstein knows selling high on his prospects is not a bad idea if the deal is right.

“You can make mistakes by holding onto your prospects too long,” Epstein said at the GM meetings last week in Phoenix, Sullivan also reported.

The Cubs are also in on free-agent starter Jason Hammel, who the team signed to a one-year deal last season, but traded to Oakland during the summer, as well as catcher Russell Martin. They have already had face-to-face meetings with the agents for both players, reported by Bruce Levine of CBS Chicago.

This is what the Cubs are now. They are players. In the Ricketts family, they have the financial resources. In Epstein and Hoyer, they have the know-how. In Maddon, they have their bench leader. Combined, they are a force in any market they want to play in, and a team that free agents can’t ignore when making their rounds.

M. Spencer Green/Associated Press

While discussing how the Cubs have remade themselves from a last-place cesspool to a destination club once again, Epstein might as well have been putting the entire league on notice.

“We hope the message is clear. Even before we signed Joe, we made it clear we are about trying to win the division now,” Epstein said, according to Levine. “Hopefully it gets their attention.”

Under Epstein’s aggressive but calculated leadership, this offseason will mark the start of a new Cubby era, one that could move the franchise from cursed to trumpeted.

Anthony Witrado covers Major League Baseball for Bleacher Report. He spent the previous three seasons as the national baseball columnist at Sporting News and four years before that as the Brewers beat writer for the Milwaukee Journal Sentinel. Follow Anthony on Twitter @awitrado and talk baseball here.