Rather than make a laundry list of things Theo Epstein needs to do when he takes over as Cubs general manager, as many others have done, I'm here to tell you that Epstein's most important task is changing the franchise's culture.
Joe Posnanski recently wrote a magnum opus on the history of the Cubs over the 66 years since they last won a National League pennant. Of his 7,375 words, these might be the most important:
A hard-nosed man named Dallas Green was hired to be GM.
Green was the best thing that had happened to the Cubs in decades. And then, just five years after Green had begun -- through shrewd drafting of players like Greg Maddux, Shawon Dunston, Mark Grace and others -- to build a good organization, he quit when Tribune Co. executives decided they wanted to limit his "jurisdiction" (as the Chicago Tribune put it) over player personnel.
This sent the Cubs wandering through various executives, eventually ending up with Jim Hendry, who was GM for nine years before being fired last August.
Hendry had some success; his teams made the postseason three times. In hindsight, that likely happened by luck rather than design. While Epstein and Oakland Athletics GM Billy Beane are prototypes of the modern GM who bloodlessly manages by the numbers, Hendry was the poster boy for the good-ol' boy network. He hired Dusty Baker as manager and Baker led the Cubs to the playoffs in his first season. But Baker, a players' manager, let the inmates run the asylum the following year and the team collapsed in a finger-pointing heap that had players calling broadcasters to complain about how they were portrayed on the air.
It was always players first with Hendry; after the playoff failure in 2008, Hendry met Milton Bradley for dinner, was charmed by Bradley ... and signed Bradley for big money despite warnings about his volatile personality. You know how that ended. He enabled Carlos Zambrano through several meltdowns until finally sending him home after Big Z's threat to "retire" in August in Atlanta.
Years before, Hendry had developed an obsession with Chad Fox, perhaps after seeing the reliever pitch against the Cubs in the 2003 NLCS. Despite Fox's injuries, Hendry signed him and kept putting him on the roster; at one point that led to a sickening sight during this 2005 game when Fox's elbow snapped (the laconic Baker said afterward, "It didn't look good"). Even then, Hendry brought Fox back in 2008 and 2009. Why? So Fox could reach 10 years of MLB service and get a larger pension someday.
Enabling players wasn't the only failure of Hendry's buddy system. His friendship with college coach Paul Mainieri led to an obsession with drafting or trading for players that Mainieri had coached, first at Notre Dame, later at LSU. The most egregious example of this was holding on to prospect Felix Pie while teams clamored for him. Pie's major league performance brought his stock down to the point where all Hendry could do was ship him in a deal that netted Notre Dame product Aaron Heilman. Two years earlier he lavished a five-year, $10 million contract on Jeff Samardzija, the money meant to assure that the Fighting Irish wide receiver would give up football. Only in 2011 did Samardzija finally give some value to the Cubs, though surely not $10 million worth.
And Hendry's final coup de ami? The hiring of Mike Quade as manager, bypassing Alan Trammell and Ryne Sandberg. What's Quade's connection? Why, he and Cubs assistant GM Randy Bush played college ball together at the University of New Orleans!
Quade managed the team as if it were a country club, allowing veterans to slide, while one day calling out young players Darwin Barney and Starlin Castro for losing a ball in the sun -- in a game the Cubs wound up losing 9-1. There was rarely accountability beyond that kind of goofy public display; veterans continued to start late into September, long past the time the Cubs were playing contending teams, while young players rotted on the bench.
Dallas Green wouldn't have stood for this; his managers wouldn't have done this. Green did raid his former team, the Phillies, for coaches, a manager and players, but he never did so unless he thought that could help him win. That's what brought Sandberg and Gary Matthews and Bob Dernier to the North Side.
There's a scene in Moneyball where Billy Beane makes phone calls in rapid-fire succession to several of his counterparts, trying to play them off against each other in order to acquire a player he covets. There's clearly no friendship involved, just single-minded determination to do whatever it takes to get the team to win.
That's what Theo Epstein needs to do. He doesn't have to "fire everyone", as some Cubs fans prefer; what he does need to do is to establish that the business of the Cubs is one thing: Winning. If that means you fire your drinking buddy, so be it. If it means trading or releasing popular players who can't help you win, get it done. I'd expect a bold move or three from Theo very soon after he's officially hired, to send the message that the country club is officially out of business.
I will close with one piece of advice to Theo -- Hire Ryne Sandberg as manager. Not because he's a cuddly Cubs icon, but because, as a minor-league manager, Sandberg has held his players accountable, while still backing them fiercely. It's been reported that Epstein nearly hired Sandberg to manage the Red Sox' Triple-A team for 2011, before the Phillies grabbed him for a comparable job. Now, Theo can hire him for a much more important spot, and begin the change in Cubs culture that is the first necessary step toward winning a championship.