Four men were put to the test in the fall of 2003: Dodgers third-base coach Glenn Hoffman, Rangers first-base coach DeMarlo Hale, Angels bench coach Joe Maddon and former Phillies manager Terry Francona.
Theo Epstein was just 29 years old then, yet surely wise enough to understand what he wanted and what he didn't want. Red Sox manager Grady Little had just famously left Pedro Martinez in too long in an American League Championship Series gone awry, but, beyond that, Little's in-game calculus, in Epstein's estimation, too often leaned more toward his own gut than the data and preparation placed in front of him. And so the young exec wanted a skipper whose thought-on-foot was influenced by actual information and intelligence, as opposed to pure instinct.
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And yes, he wanted somebody who could corral a clubhouse full of big characters.
"We had a veteran club," Epstein said Monday, on the eve of the World Series at Progressive Field. "So we were looking for a manager who maybe fit that a little more directly."
Those four coaches were put to a test, a simulation. A tape of a game was played and paused at specific spots in which the candidate, who was given lineup cards, stats, notes on relievers' workload and other relevant info, was asked what he would do in that situation and why.
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Francona passed the test, and it's no cliché to say "the rest is history." The following fall, Francona and Epstein made history together, breaking Boston's 86-year World Series championship drought.
Now, those two men are pitted against each other, with more history on the line. Epstein's Cubs haven't won a World Series in 108 years. Francona's Indians haven't won one in 68 years. Their curse-breaking abilities are about to be put to a different type of test, and only one of these friends is going to come out on top.
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Tito vs. Theo. What a story.
"It's wonderful," Epstein said. "It makes it even more special. Being in the World Series is special on its own, but it brings back a lot of good memories. I'm really proud of him and the job that he's done over there. The only misgivings I have about it is, as great a manager as he is, he's an even better postseason manager. So maybe we wish we were going up against someone else."
The praise was equally effusive coming from the other side.
"I used to get asked a lot about Theo when he went to Chicago," said Francona, "because I had been with him for eight years. I was pretty consistent in my answer that he was too smart and too hard-working to not make it work. That's come true."
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Francona and Epstein spent eight years together, which is a lifetime in professional sports. Add in the fact that they spent those years in Boston, one of the most heated media markets in the game, and you can at least double the effect of that duration.
"Eight years in Boston," said Francona, "is, I would almost say, miraculous."
These men made a miracle happen in Boston, and they were one of the most successful collaborations in history.
Epstein saw something in Francona that day of the simulation, when he quite literally got in the future manager's face and asked him how he'd handle the situation on the screen. Before that interview process, Epstein and Francona didn't know each other. Epstein just knew Francona's reputation as a player's manager -- and a favorite of the newly signed Curt Schilling -- from his otherwise unsuccessful (.440 winning percentage) time in Philly. And Francona just knew what he heard about Epstein from his close friend, then-Indians exec Mark Shapiro, who gave Tito the sage advice, "Don't B.S. him."

It didn't take long for the two men to know they'd work well together.
"I went home knowing this was a place I wanted to end up," Francona said at his introductory news conference. "All of the things they seem to believe in -- communication, open and honest communication, the way you treat people, their view on the game of baseball -- it just seemed like a terrific match."
In some ways, it was an unusual pairing. Epstein and his front-office crew were closer in age to Francona's 18-year-old son, Nick, than they were to the 44-year-old Francona himself. But the still-unproven skipper and the young GM hit it off. Francona would sit in on the poker games that would take place at the Fort Myers, Fla., rental where Epstein and Co. spent Spring Training, and the conversations and friendship forged there would serve them well both in a trying second-place season that included the brave and highly controversial trade of star shortstop Nomar Garciaparra and an unforgettable October that would include a historic comeback against the rival Yankees and a sweep of the 105-win Cardinals in the World Series.
If Epstein and Francona had only that year to show for their efforts, it would be enough. But of course, in eight total years of attachment, they'd reach the postseason four more times and win it all again in 2007.
Alas, the 2011 season ended with the chicken-and-beer-fueled September fiasco that eventually sent both men to embark upon other challenges. Francona spent a season on the small screen, working in an ESPN role that was never truly comfortable for him before surprisingly settling in with a Tribe team that, because of his father's playing past, felt like family for him. And Epstein took on one of the most enticing -- and unforgiving -- challenges in all of professional sports, a total teardown of the Cubs with an eye on erasing the ghosts and the goat on the North Side of Chicago.

Epstein used to refer to his relationship with Francona as akin to "an old married couple." They had their behind-the-scenes battles, certainly, days when the computer-aided whiz kid and the baseball lifer approached the same situation with totally dissimilar perspectives and had to hash things out. But far more often than not, they hashed things out, and they have a lasting legacy in one of the game's major markets -- and a friendship that has stood the test of time -- to show for it.
It would only be appropriate, then, for one guy to have to get through another to end another enduring drought and establish another legacy.
"We've been through a lot together," said Epstein, "and it's pretty cool to be up against him."