Theo Epstein once traveled to Arizona for Thanksgiving dinner at Curt Schilling's house. No word on how many slices of pumpkin pie he devoured, but over turkey and dressing he laid the groundwork that ultimately convinced Schilling to waive his no-trade clause, come to Boston and change history.
Last October, Epstein traveled to a small patch of sandy beach in the Florida panhandle to conduct a job interview over a few beach chairs, some wide-mouth bottles of beer and a $20 bottle of wine, working through sunset to convince Joe Maddon to come manage the Chicago Cubs and change history.
Clearly, history is no match for a boarding pass and a corkscrew when baseball's greatest miracle worker zeroes in on a plan to change water into wine.
Hyperbole? Stay tuned. As the Chicago Cubs launch their first postseason since 2008 with Wednesday's National League Wild Card Game against Pittsburgh, if they can deliver a World Series title this year or soon with this nucleus, Epstein may be retrofitted for his own personal wing at the Baseball Hall of Fame.
"It would be pretty cool if he did it," says Padres president Mike Dee, who worked with Epstein in Boston and, before that, in San Diego, and remains close with him today. "To be able to be the architect of both the Cubs and the Red Sox ending long droughts?
"It would be hard to believe one guy would be involved in ending both of those."
Do the math: When Epstein's Red Sox won the World Series in 2004, it ended an 86-year curse. The Cubs currently are in season No. 107 since last winning a World Series title in 1908.
Together, that is a combined 193 years.
If, with a Schilling and Anthony Rizzo trade here, a Dave Roberts and Jake Arrieta deal there, a Jon Lester signing and a Maddon wooing, Epstein could make nearly two centuries of misery disappear for a pair of baseball's crown jewel franchises?
Hyper-focused and acutely aware of the fragility of success, Epstein himself won't bite.
"Let's see if we can win a single postseason game first—it's been a while!" he says in an email conversation with B/R. "I don't like to get ahead of myself."
No worries. His precocious Cubs, who hit the accelerator this summer at least a year ahead of projections, are doing it for him.
"The way Theo's brain works, he probably could have done whatever he wanted to do," says Kevin Towers, the former longtime Padres GM who was running the club when Epstein started full time in baseball in 1995 as an intern in San Diego's media relations department.
"I think he would have been successful in baseball if he was a thespian. It's who he is. He was made for it."
Theo Epstein comes from a family of writers. His grandfather and great-uncle won an Academy Award for the Casablanca screenplay. His father, Leslie, now teaches fiction writing at Boston University, where he was the director of the creative writing program for more than 30 years. His sister, Anya, was a screenwriter for, among other things, television's Homicide: Life on the Street.
Yet, nobody in the Epstein family has authored something quite like what may be a rough draft or two from becoming one of baseball's greatest stories ever written.
Today, at 41 and long past the proving-ground stage of his meteoric career, the heavy-lifting begins not so much with the selling as with trust.
"A lot," Maddon says of the one key ingredient, aside from the five-year, $25 million contract, that led him to Epstein and the Cubs. "Obviously, when it got to that particular point and we were talking, I had heard and read so much about the young Cub players.
"You hear about it and read about it, but you just don't know about it. Obviously, I did more research as we got closer to having to make a decision, and it's really exciting for me to work with this bunch of young players who have a tremendous upside for years to come.
"And, of course, the reputations of Theo and Jed [Hoyer, Cubs general manager and Epstein's longtime consigliere], I got to know them a little bit from a previous interview with the Red Sox years ago. So I always felt like we had this common ground.
"I definitely trusted them from the beginning, and it's as I thought it would be."
Last winter, Lester spurned the Red Sox and the World Series-champion Giants to sign a six-year, $155 million deal with the Cubs, bringing him, in a sense, full circle: Though Lester was drafted the summer before Epstein arrived in Boston in November 2002, it was Epstein who was in charge when Lester came of age as a Red Sox rookie in 2006.
"The biggest thing for me is believing and knowing his process," Lester says. "I saw it firsthand. I was a part of that process.
"Obviously, I wasn't drafted by him, per se. But I wasn't one of the guys that he got rid of, so he obviously saw something and brought me along. And he had that core in Boston similar to the Yankees [of Derek Jeter, Jorge Posada, Andy Pettitte and Mariano Rivera].
"I've seen it. I've lived it. And when you come over here, it's kind of the same thing. You can see things as they go. The process has kind of sped up on him a little bit. I don't think they fully thought that we would perform the way we have this year, which is a good thing."
Epstein no longer is the Boy Wonder of 28 that he was when Boston made him the youngest GM in the history of the game in 2002, after which he responded with World Series titles in 2004 and 2007. He is older and wiser, and the "process" of which Lester speaks has been time-tested and proven.
"Everyone assumes that because Theo is young and has an Ivy League education, that he's a Moneyball stats geek," Dee says. "Where I was always impressed with Theo is that for every stats guy he had sitting at a computer, he had an old-school guy like Bill Lajoie [the late former Tigers GM and longtime scout] around the batting cage.
"He had a system of checks and balances. He looks through the baseball lens differently than he looks through the Sabermetric lens. He's always been great at that."
You could say Epstein has been constructing rosters since the day he stepped into baseball, following his graduation (with a degree in American studies) from Yale.
In those early days, his roster construction involved helping then-San Diego media relations director (and now Miami Marlins radio voice) Glenn Geffner produce the Padres media guide.
"He'd hang around over on the baseball side," Towers says. "You could tell that's where he ultimately wanted to get to.
"He had such tremendous writing skills, but that wasn't what he wanted to do."
Instead, he would write his masterpiece in a different way. He volunteered for whatever the baseball department needed doing. Ran the JUGS radar gun behind home plate. Went to minor league games.
Today, what Epstein remembers most about those blank-canvas days is the Padres' push to win the NL West in 1996 and the World Series run in 1998. And the people: Towers. Executives Ted Simmons and Fred Uhlman. Scouts like Ken Bracey, Brad Sloan, Bill Gayton and Eddie Epstein.
"We were a small-market team with a small front office," Epstein says via email. "So I learned a lot about being resourceful and got exposed to all the different sides of baseball operations.
"It was the perfect training ground."
It was easy to see his potential, which is why then-Padres president Larry Lucchino advised law school, because it would make him even sharper and more well-rounded. Nights, between baseball tasks, that's exactly what Epstein did, at the University of San Diego.
"He's always been an incredibly intelligent young man," Towers says. "We'd give him a project that would take other interns weeks to do, and he'd stay up all night to make sure it was on your desk the next morning. There wasn't anything he couldn't do."
They would watch minor league games together and Epstein would write up reports. He got to know the scouts.
"Intellect, numbers, he had a great blend of both," Towers says. "I liked him a lot because he's got great people skills, the scouts liked him and as he got to know the players it made him more whole. He wasn't strictly a numbers guy who only knew numbers people.
"All of a sudden, he was a baseball guy who knew baseball people."
As Towers recalls, shortly after Epstein finished law school at USD in 2000, a Newport Beach law firm came recruiting. They sent a limo, wined and dined him and offered him a job somewhere in the $150,000 range. At the bottom of the Padres' organizational flow chart, Epstein was making maybe $30,000 at the time.
"Theo came back and said, 'It was pretty cool, but I really want to stay in baseball," Towers recalls.
So the Padres bumped up his salary by a few thousand, gave him the title of "Director of Baseball Operations" and increased his responsibilities. Now, Epstein was engaging with other clubs in personnel discussions, talking with the Padres' scouts, gaining responsibilities. The raise pushed him to roughly $60,000 a year—still less than half of what that law firm offered.
Not long afterward, then-Toronto GM J.P. Ricciardi phoned, wanting to hire Epstein as the Blue Jays' assistant GM.
"What should I do?" Epstein asked Towers.
"Theo," the Padres GM said. "You're probably more involved here; you're basically doing that here in San Diego. Where would you rather live, San Diego or Toronto? You've still got good visibility here; it's a good place to live. Unless the money is more…"
"It's not about the money," Epstein said. "I'm happy."
"I said, 'What do you want to do?'" Towers says. "He said, 'I want to run the Red Sox.'
Within a year, he was their GM.
Nobody won an Academy Award for writing the script for the movie Moneyball. And as entertaining as the film is, real life didn't quite play out that way.
Oakland president and GM Billy Beane originally was offered the real-life role of Red Sox GM in 2002 and, had he not had a change of heart and reneged after accepting the job, who knows which route Epstein would have run to the ball?
Beane-to-Boston would have been the ultimate power play at the time for a new Red Sox ownership group that had sacked Dan Duquette and was looking to make an enormous first-impression splash. Instead, when Beane sent his eleventh-hour regrets, the Red Sox were left scrambling. They could turn to one of their second choices. Or, they could get creative.
This is where passing on that Blue Jays job turned fortuitous for Epstein. When Lucchino left San Diego following a falling out with then-Padres owner John Moores, he landed softly in Boston as part of the ownership group with John Henry and Tom Werner. And, while doing so, he ransacked the Padres' organization of some of its best minds…including Epstein.
Lucchino knew that, in Epstein, he had a future star. Abandoned by Beane and knowing they had a veteran support system in place that could back, nurture and teach a young GM, the Red Sox decided, why not?
"When Theo got the job, his father gave him two words of advice: 'Be bold,'" Dee said. "He told him, don't look back in five years and say you should have been more aggressive."
Says Epstein: "It was great advice."
Over the next few years, the Red Sox had a Dream Team of impressively sharp kids working in baseball operations who would move on to become future stars. Hoyer. Josh Byrnes, the current assistant GM with the Los Angeles Dodgers and past GM of the Arizona Diamondbacks and San Diego Padres. Peter Woodfork, who now works in the commissioner's office.
But, they also employed salty old baseball minds like Lajoie, Allard Baird (the former Kansas City Royals GM), Craig Shipley (a former major league infielder) and Bill James, the Godfather of Sabermetrics.
"When he got the job, he was GM-ready," says Dee, who also had moved from San Diego to Boston with Lucchino and was the Red Sox's Chief Operating Officer from '03 to '09. "People mistook him for a 25-year-old kid. But he never played to his age.
"His Boston success and, ultimately, his Boston departure set him up to have the intestinal fortitude for what he's doing now in Chicago."
Working for Lucchino, as those who have done so will tell you, is not for the weak of heart. He is a tough and demanding boss. He looks over your shoulder and screams, "Why?" when you've made a decision, and you'd better have good reasons. And just when you think you've reached a decision, he quizzes you on all of the avenues that led to your decision. And you better have covered every base, so to speak, during the process.
The relationship between Lucchino and Epstein always was going to be complicated and destined for a combustible breakup. Epstein could only be groomed for so long. There would be a point where he was fully formed with enough experience to operate with the autonomy that would be difficult for Lucchino to allow.
"Larry and Theo have two of the most ferocious pilot lights you'll ever see," Dee says. "In many ways, they're a lot alike. Intellectual capacity, the will to win, the ability to look at things differently.
"An enormous avalanche of success came to us pretty quickly. It's unfortunate it ended the way it did, initially. But things happen when you're dealing with competitive people at the top of their profession. Larry's RPM level is amazing. And Theo's…"
His father's advice, be bold? Never was Epstein bolder in Boston than in the minutes leading up to the July 31 trade deadline in 2004 as the Red Sox doggedly chased the Yankees. Frantically racing the clock to complete a three-way trade, he sent Boston icon Nomar Garciaparra to the Cubs and acquired first baseman Doug Mientkiewicz from the Twins and shortstop Orlando Cabrera from the Expos.
The Garciaparra trade stunned almost everyone in town.
"We just traded away Mr. Boston, a guy that meant so much to the city, and just like that, he's gone," then-Red Sox outfielder Johnny Damon told the Boston Globe's Bob Hohler at the time.
That same day, Epstein also acquired speedster Dave Roberts, just the piece then-manager Terry Francona needed to pinch run in the ninth inning of Game 4 of that fall's American League Championship Series to ignite one of the greatest comebacks in baseball history. Roberts' dash to second base with Mariano Rivera on the mound was the most memorable run through Boston since Paul Revere, and it ignited Boston's storming back from a 3-0 series deficit to win the World Series title that smashed the famous Curse of the Bambino.
Once that happened, the Red Sox's '04 World Series title, the franchise's first since 1918, was a foregone conclusion.
While nobody in Boston would trade those days for anything, there also was no going back. Epstein had cut all of his adult teeth and was ready for his independence. Lucchino wasn't as quick to back off. History has seen fissures like this in how many father-son, boss-mentor relationships since the dawn of civilization?
"The trade deadline of '04, it was magical watching those guys work together," Dee says of Theo and his baseball operations team. "Sometimes things happen, and as they're happening, you're like, 'How is this happening?'"
Behind-the-scenes pushes came to shoves, culminating with Epstein's stunning resignation in 2005, and his Halloween night escape from Fenway Park disguised in a gorilla suit.
"We were family, and it was hard to see family go through that type of stress," Dee says. "All of us were close to both people."
The Red Sox wooed him back two-and-a-half months later. Lajoie ran the team in the interim, Lucchino and Epstein publicly made nice and Epstein returned to his GM role with far greater autonomy. They won a World Series again in '07, but it wasn't the same. It never is. Not that things were bad. They were just…different.
And then, he left.
"September of 2011 was a terrible month," he emails of his final days in Boston. "I think we had the best record in baseball and were on pace for 100 wins entering September, and we threw it all away because we ran out of pitching and didn't handle adversity well as a team. It could have been such a special year, with an uber-talented team and a terrific draft. Instead, it turned into a big mess."
Out of that mess, the Cubs lured him with a five-year, $18.5 million deal and the title president of baseball operations.
Turns out, as his father told him, being bold doesn't leave a guy looking in the rearview mirror wishing he had been more aggressive. But it also is no safeguard against regrets.
"Theo checks every box," Towers says, speaking of the qualities you want in a top baseball executive. "Scouting, knowing a network of coaches and players, the ability to evaluate, the ability to do contracts, people skills, as a public speaker, and he's incredibly competitive.
"There were times I'd tell him, 'Theo, I love you like a brother, but there are times I don't trust you. I think you'd probably slit my neck and cut my throat to win.'
"He said, 'You're probably right.'"
Which brings us to today, the Cubs, Maddon…and Rick Renteria.
It was last October when Epstein and Hoyer traveled to Florida to meet with Maddon. Rizzo, Arrieta and Jorge Soler were already in place. Kris Bryant, Addison Russell, Kyle Schwarber and Javier Baez were on the farm. And the Cubs were edging past three difficult seasons of rebuilding.
The then-Tampa Bay manager had employed a clause to opt out of his contract and suddenly had become a surprise free agent.
History, again, has proven Epstein correct. The luring of Maddon, whom Epstein had interviewed years ago for the Boston job before Francona was hired, is one enormous reason why the Cubs smashed open their window to win far earlier than anyone imagined.
But it was messy. Renteria, a longtime baseball man and good soldier, had just finished his first season as Cubs manager and had already been told he would return for 2015. To hire Maddon, the Cubs had to discard Renteria like an empty, recyclable plastic bottle.
They kept him apprised every step of the way. Hoyer flew to Renteria's Southern California home to personally explain the club's intentions with Maddon. They offered Renteria another job within the organization. Renteria declined and has not been seen publicly in baseball circles since.
At the time, Epstein issued a long explanatory statement that read in part:
"Last Thursday, we learned that Joe Maddon—who may be as well suited as anyone in the industry to manage the challenges that lie ahead of us—had become a free agent. ... We saw it as a unique opportunity and faced a clear dilemma: Be loyal to Rick or be loyal to the organization. In this business of trying to win a world championship for the first time in 107 years, the organization has the priority over any one individual. We decided to pursue Joe."
I think you'd probably slit my neck and cut my throat to win.
Twelve months later, the young, Maddon-led Cubs produced the third-best record in the majors. And if they can get past the Pirates on Wednesday, who knows where this autumn might lead. Possibly, dare we say it, all the way back to 1908.
"In some respects, it has been more difficult than expected," Epstein says via email of the job in Chicago. "The Collective Bargaining Agreement [signed in November, 2011, just a month after Epstein took the Cubs job] made it impossible for us to hoard draft picks, we had a massive young talent deficit and we actually had to bring the payroll down.
"But in other respects, we had more going for us than we imagined: It turned out that we had an incredibly patient and supportive owner [Tom Ricketts], the fanbase was great to us and we were able to be single-minded about the rebuild without much distraction."
Going into this season, the Cubs had made 38 trades since the arrival of Epstein, including the Arrieta heist from Baltimore on July 2, 2013 (along with reliever Pedro Strop and international slot money for pitcher Scott Feldman and catcher Steve Clevenger).
They acquired Rizzo from the Padres in a four-player deal that sent pitcher Andrew Cashner to San Diego in January 2012. They acquired Russell by trading pitcher Jeff Samardzija to Oakland last July and they signed Soler to a nine-year, $30 million deal in June 2012.
Throughout, Epstein has operated as he has all of his life, with a rare combination of exceptional intelligence and street smarts, blending scouting and Sabermetrics as naturally as both sides of the brain working in concert together.
"I think Theo is the first guy to demonstrate before anybody else that you need the equilibrium of both," Dee says.
From Boston to Chicago, Lester sees subtle differences.
"I think he probably has lightened up a little bit," Lester says. "In Boston, it always seemed like he had that thumb on him at all times."
Says Epstein: "I'm probably a little bit more mature, more experienced and [have] a better sense of how to manage time and work-life balance."
Through their shared history together and a winter of negotiating, Lester was able to view a side of Epstein that remains hidden from others. The back and forth when Lester and his wife, Farrah, were making one of the biggest decisions of their lives: How does living and playing in Chicago compare with Boston? What about Wrigley Field and the working conditions? What is the family room like, compared with Fenway? Conversations. Emails. Texts.
"You get to sit down and continually talk to somebody for two months, two-and-a-half months, three months; you start to build that relationship a little to where the guard is let down and it's not just a GM or president and a player, it's more on a personal level," Lester says. "So I got to see that a little bit.
"I think his personality has pretty much stayed the same. His passion for what he does has probably stayed the same if not grown a little bit coming from Boston to here and trying to create a winner.
"Obviously, his baseball mind hasn't changed. He still believes in the same things as he did in Boston: build the farm system, try to build from within and then bring in pieces when you can."
When the Red Sox won it all in '04, the team employed only one homegrown player on its roster, Trot Nixon. When they won again in '07, Epstein's fifth season on the job, eight products of the Boston farm system were on the roster.
So maybe he's lightened up a wee bit simply because, as with the rest of us, time and family have a way of smoothing the rough edges. Age can't help but expand your world.
No longer is Epstein the young, single, ambitious kid eager to finish a project for the boss by the morning's first light.
Now, he's married with two sons, Jack, 7, and Drew, 1.
"I wouldn't say I'm more relaxed," he says via email. "I think we've been pretty locked in, pretty intensely focused the last four years. We felt like there was only the smallest of margins for error with this big-market rebuild, so we needed to get it right."
The fear of getting it wrong still keeps him up late into the night, working, studying, emailing. But for the first time in his four years there, autumn has come to Wrigley Field and the construction cones are few and far between.
Already kind to Epstein, history at this point is preparing to jump up onto his lap and begin warmly licking his face.
"We believe we're going to [win]," Maddon says. "Of course, when I came on board, we talked about doing it this year because, like I said, why would you not want to aim high?
"Why would you not want to aim high?"
Scott Miller covers Major League Baseball as a national columnist for Bleacher Report.
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