Theo vs. Tito: How this World Series is a battle between Red Sox royalty

The Indians' manager Terry Francona and Cubs' GM Theo Epstein are still beloved in Boston. Both are trying to repeat the feat of bringing home championships to cities with long-suffering fans.

First Look

This year’s World Series is a matchup made in Boston.

From the dugout of the Cleveland Indians, manager Terry Francona is observing the team’s decisive final games with the same poise that in 2004 helped bring the first championship to Boston in 86 years. In the box seats, Chicago Cubs general manager Theo Epstein is watching, too, but from the other side of the diamond.

The partnership between Mr. Epstein and Mr. Francona dissolved after the spectacular flop of the Red Sox in the final month of the 2011 season, one followed by somewhat lurid explanations for how the team’s management lost its grip on the reins. Still, the two figures remain beloved in Boston for their 2004 and 2007 championships. And their partnership embodied a new wave in baseball leadership, one that combined statistical savvy with an egalitarian approach to dealing with players.

In 2004, The Christian Science Monitor described Epstein, a Boston-area native who at 28 years old had recently become the youngest general manager in the history of Major League Baseball, as “the most visible specimen in a new breed of baseball executives who use statistical analysis to crunch baseball's hallowed numbers in new ways, trying to shine fresh light on a century-and-a-half-old game.” That new reliance on mathematics demystified decision-making, shifting power from wizened dugout folk to general managers and other front-office heads. 

By now, the "Moneyball" ethos is deeply embedded in the business of baseball. Less so, for another Epstein and Francona trademark: their insistence on leveling with players, who often feel suspicious of management. 

For Epstein, it stems from his first job in baseball, when San Diego Padres infielder Craig Shipley informed him that every player had "been lied to by management – or thinks they’re about to be lied to by management,” Epstein told The New York Times this week. 

“That helped the light bulb go off that, yeah, you can get a real advantage just by being honest with your players all the time." 

Many of Francona’s former players describe a similar approach from the manager. 

“He’s a genuine person, and you can talk to him about anything,” Indians first baseman Mike Napoli told the Times. “He’s going to tell you the truth. He wants you to do good, he wants to talk to you, and that’s for everybody in the clubhouse. It’s nice to come to the park every day knowing that’s your leader and he has your back.” 

That may help explain why Epstein jumped to hire current Cubs manager, Joe Maddon, to work with a young, talented roster. If there’s anyone who deserves the “cool manager” tag more than Francona, it’s Mr. Maddon, whom the New Yorker’s David Axelrod branded an “ageing hipster and baseball savant” in a September profile of the Cubs.

"An aficionado of vintage cars, he pulled up in his 1976 Dodge van, cigar brown with gold detailing and a Western landscape painted on the side,” wrote Mr. Axelrod. "The interior is lined with orange shag carpet, and the seats have ostrich-leather trim.... It was the same van that Maddon had driven onto the field in the early weeks of training camp, emerging in a tie-dye shirt and stars-and-stripes headband, his custom speakers blaring the inspirational sounds of Earth, Wind & Fire’s 'Shining Star.' Maddon is more than a manager. He’s a show."