Major League Baseball

Theo facing toughest test with Cubs

Published Apr. 25, 2012 1:00 a.m. ET

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Theo Epstein's mama didn't raise a fool. He knew when the getting was good, and he got out of Boston just in time.

After nearly a decade of excellence, the Red Sox are now paying the price for focusing on the present at the cost of the future, which has left Epstein’s successor as Red Sox general manager, Ben Cherington, with no honeymoon in his new position.

Epstein, Boston’s former general manager, meanwhile found a soft landing in Chicago with a five-year, $18.5 million contract. To get him to accept the challenge of exorcising the demons haunting the Cubs, a feat he accomplished with the Red Sox, the Cubs also named him president of baseball operations.

Maybe Epstein was ready for the new challenge. Maybe he needed to be reinvigorated.

Change of scenery can work wonders.

It was, after all, apparent that Epstein was in need of a move following the 2005 season when he walked out on the Red Sox, only to return shortly before spring training opened in 2006.

The youngest general manger in history when he was put in the position with the Red Sox at the age of 28 on Nov. 5, 2002, Epstein earned the Boy Wonder title by proving the impossible was possible.

He provided the finishing touches to a roster that ended the Red Sox’s 86-year drought by claiming a world championship in 2004, reducing the Curse of the Bambino to a fairytale for future generations.

And for good measure, with Epstein in his second tour with the Red Sox, Boston won another World Series in 2007.

The truth, however, is that since that celebration in 2004 Epstein has appeared to lose his edge.

Red Sox president Larry Lucchino had long been his guardian angel, taking him from an intern in Baltimore to the San Diego Padres. Epstein first worked in the media relations department and later as the director of baseball operations with the Padres, all while earning a law degree at the University of San Diego.

Not long after Lucchino assumed the role of president/CEO of the Red Sox in November 2001, he brought Epstein with him. Lucchino then put him into the role of general manager a year later.

Over time, however, Lucchino’s micromanaging gets old. That, as much as anything, was what Red Sox insiders said led to the Halloween 2005 resignation of Epstein. And as rich as his deal may have been to return nearly three months later, the hard feelings that had developed between the two never softened.

There are Red Sox observers who feel the front office friction took a toll.

It wore on manager Terry Francona, who would have as many as six suggested lineups sent down from the front office on a daily basis. He eventually was made the scapegoat for the Red Sox struggles.

It wore on Epstein, who took advantage of the get-of-jail-free-card offered by the Cubs and left his former assistant Cherington to deal with Lucchino, who paid little attention to the recommendations of his front office staff and hired Bobby Valentine as the manager.

That created instant uneasiness between the dugout and front office. The struggles of a franchise without a dependable bullpen, steady shortstop and suddenly lacking rotation didn’t allow for any calming of the seas. And a farm system depleted of high-level prospects to patch big-league holes in recent years has no quick help on the horizon.

That, however, is no longer Epstein’s concern.

Now it is Epstein’s challenge to show that he can provide the lift for the Cubs he initially provided the Red Sox, and that the slow but steady decline during his second term in Boston was more a product of environment than anything else.

Yes, the Red Sox won that second world title in 2007, but the key additions to that team were the result of the work of the late Bill Lajoie and Cherington. The two worked together to keep the Red Sox moving forward during the three-month absence of Epstein in the winter of 2005-06, including the trade that brought Josh Beckett and Mike Lowell from Florida.

Then came a loss in the American League Championship Series in 2008, a loss in the AL Division Series in 2009 and then back-to-back third-place finishes, a failure in the minds of a Red Sox nation that was spoiled by the previous success of the Epstein era.

Now Epstein has turned his attention to the Cubs, no longer considered loveable losers by a fan base that has had a small taste of the postseason recently, including back-to-back National League Central titles in 2007 and '08. The fans now hunger for the World Series, where the Cubs haven’t appeared since 1945, and haven’t celebration a championship since back-to-back world titles in 1907 and '08.

And the challenge with the Cubs makes Boston look like a tea party. With the Red Sox, a foundation was in place. Ownership hadn’t mettled, and the previous general manager, Dan Duquette, had the house in order.

In Chicago, former general manager Jim Hendry never had a chance. As much as he tried to build a foundation, he constantly had interference from above, forcing questionable contracts on the payroll that took a long-term toll without any short-term results.

Epstein has been promised freedom to do the job the way he feels it should be done.

Time will tell whether he is up for the challenge.

Can he rekindle those early days in Boston, or were the last five years an omen of what lies ahead?

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