How Theo Epstein broke another curse and built the World Series champion Cubs

·MLB columnist

CLEVELAND — On the night the Chicago Cubs won the World Series, Theo Epstein, the man who rescued them from organizational rubble and molded them into a champion, and Tom Ricketts, the man who hired him, embraced for almost a minute amid flying Champagne corks popped by the 25 men who did what 108 years of Cubs teams couldn’t. Game 7 of the 112th World Series, one of the finest displays of pulse-thumping baseball ever offered, was over, and it belonged to the Cubs, now and forever.

“We did it,” said Epstein, the Cubs’ president of baseball operations, as he hugged Ricketts, the team’s owner who had hired him five years earlier to do what he’d done for the Boston Red Sox: play rainmaker for an interminable title drought. “Got through the tough times,” Epstein said, and he started talking about when, in his first year, the Cubs took out a full-page ad in a newspaper trying to sell individual-game tickets, accidentally transposed two digits in the 1-800 number listed and ended up sending prospective customers to a phone-sex line. Ricketts laughed. Those were the old Cubs. Today they could call themselves champions.

Imagine that. The Chicago Cubs, America’s saddest-sack sporting franchise, the one that had carved its identity in a mountain of failure, had beaten the Cleveland Indians, 8-7, in a 10-inning, four-hour and 28-minute display of sporting beauty that frayed the nerves and palpitated the hearts not just of the two cities that lived and died with every run scored but a country reminded why baseball is the national pastime. It may have been the greatest game ever played in what may have been the best World Series there ever was. Even if others care to stake their claims, the Cubs and Indians brute-forced their way into history. This was the most anticipated series in ages, and it exceeded each and every one of its expectations, most of all the game that started Wednesday and bled into the early hours of Thursday.

Game 7 brought out the best and worst in the Cubs and Indians and everyone whose emotional attachment to the organizations coursed through Progressive Field, where 38,104 people packed themselves, including Epstein, his wife, Marie, and their son, Jack. They sat in the stands, ready to witness the Cubs claw back from a three-games-to-one deficit. Passions ran deep for the Indians, too, with their 68-year championship famine and the prospect of blowing what felt like an insurmountable advantage after Game 4 palpable. Early in the game, two fans sitting near Epstein were harassing him and his family. He asked them to stop. They refused. He summoned security. Before being escorted out, a woman doused Epstein and his son with a cup of beer.

“The rest of the night,” Epstein told Yahoo Sports in a private moment after the Cubs’ celebration in Cleveland started to abate, even as the one in Chicago still raged, “was pretty amazing.”

All of it felt too fresh to process, this game between two teams whose gas tanks hovered well below E calling upon every last morsel of energy to guarantee themselves a parade, a ring-fitting and a legacy. These Cubs, like the 2004 Red Sox that won a championship after 86 years of disappointment, were built with the deft hand of the now 42-year-old Epstein, baseball’s own Gaudi, an architect nonpareil with an inimitable style. This was his team, his doing, all the way down to the final out, with third baseman Kris Bryant, drafted by Epstein, smiling as he fielded a groundball and rifling it to first baseman Anthony Rizzo, a trade acquisition of Epstein’s.

And just like that, a tale of frustration passed generation to generation, of habitual regret, of an identity fostered around something so antithetical to sports – losing – vanished. All month, when he was home, Epstein would drive around the city of Chicago, around the Wrigleyville neighborhood where he lives, and see the white flags with blue Ws that hung every time the Cubs won. He would start to choke up. He grew up in the shadow of Fenway Park and understood what breaking one curse meant. The prospect of abolishing another spoke to him.

Especially with what it would take.

“October’s crazy, in a great way,” Epstein said, “and this may have been the craziest.”


Theo Epstein gets showered in champagne by Bill Murray. (Getty Images)
Theo Epstein gets showered in champagne by Bill Murray. (Getty Images)

Six minutes before midnight, the rain came. For nearly four hours, the Cubs and Indians had played a pulse-pounding brand of baseball. Dexter Fowler’s leadoff home run, replete with a backward trot between first and second base. Cleveland answering with a run of its own. Chicago extending its lead to 2-1, then 3-1, then 4-1, then 5-1. Cleveland answering again by scoring two runs on one wild pitch. The Cubs getting one back on a home run from retiring catcher David Ross, in his final major league game, off the heretofore-unhittable Andrew Miller. And then the magical eighth inning when, after the Indians plated one run, Rajai Davis, an outfielder with 55 career home runs in more than 1,200 major league games, turned on a fastball from Aroldis Chapman, the hardest-throwing pitcher in baseball history, the one Chicago acquired for this very moment, and sent it over the 19-foot wall in left field for a game-tying two-run home run. It wound up one of the biggest footnotes in World Series history.

Because after a clean ninth inning came the 17-minute rain delay, during which the Cubs, prodded by outfielder Jason Heyward, gathered in a weight room just off the visiting dugout. Inside is a treadmill, a few machines, a shelf of free weights. All 25 of the Cubs congregated. Chapman was on the verge of tears, worried he had blown the World Series. No, Heyward said. He hadn’t blown anything. This was the best thing that could’ve happened.

Epstein happened to be walking by the weight room, on his way to talk with MLB about the delay. He cracked the door and won’t ever forget the first words emanating from the room: “This is only gonna make it sweeter.”

“As soon as I heard that,” Epstein said, “I thought we were gonna win.”

Kyle Schwarber led off the 10th inning with a single off Indians reliever Bryan Shaw. Albert Almora Jr. pinch ran for him and advanced on a flyout. Cleveland intentionally walked Rizzo. Ben Zobrist doubled to score Almora. Cleveland intentionally walked Addison Russell. Miguel Montero singled to score Rizzo. The lead was 8-6. The Cubs needed three outs.

In came rookie Carl Edwards Jr. He secured two quick outs. Then he walked Brandon Guyer, who took second base before Davis drove him in. It was a one-run game. Cubs manager Joe Maddon, maligned for his use of Chapman in recent days, for the two-strike squeeze bunt Javier Baez failed to execute in the ninth – for the decisions that can win or lose a World Series – would leave the last out in the hands of a left-handed pitcher who came to the Cubs around the trade deadline, just as expected.

Nobody, of course, thought it would be Mike Montgomery. He was a 27-year-old who never had recorded a save in any of the 243 professional games he pitched, and Maddon wanted him to get his first in Game 7 of the World Series.

“Hey,” Cubs reliever Justin Grimm called to Montgomery as he exited Chicago’s bullpen, “you’re going to be on the highlight reel forever now.”

And so he will. Montgomery induced Michael Martinez’s groundball that went to Bryant, and the Cubs converged near the pitcher’s mound in an amorphous blob of hugs and high fives and tears. They slipped on championship shirts and replaced their in-game hats with championship versions and asked each other if they could believe it and said no, even if this was what they’d dreamt of. They started the booze showers as fans moved to the lower bowl to chant “Let’s go, Cubbies,” and sing “Go Cubs Go,” a cappella, as the clock moved past 1 a.m. Bill Murray was honking the horn on the convertible won by Zobrist, the World Series MVP, and Eddie Vedder, the Pearl Jam lead singer and Cubs superfan, was sitting on the bench, almost catatonic, and all of this would’ve been a gorgeous display of spontaneity were it not so long in the making.


Cubs president Theo Epstein celebrates the franchise's first championship in 108 years. (Getty)
Cubs president Theo Theo Epstein celebrates the franchise’s first championship in 108 years. (Getty Images)

On the morning of Oct. 31, the day between Games 5 and 6, Theo Epstein and Jed Hoyer, his consigliere, his confidant and his organization’s general manager, were talking about their Halloween costumes. One of Maddon’s traditions, first in his tenure as Tampa Bay Rays manager and now in his two seasons with the Cubs, was to have his team dress up for flights. Never was there a better excuse to get a little weird than Halloween.

A few weeks ago, Hoyer’s mother-in-law delivered him a plush bear mask. He’d go as a cub. Epstein liked the idea of a mask. And he knew exactly what he wanted to be: a gorilla.

Those who understood chuckled. Epstein had famously escaped Fenway Park 11 Halloweens ago wearing a gorilla suit after a feud with ownership prompted him to resign as Red Sox GM. He would return and win a second World Series in 2007, but his relationship with the organization never was the same. By 2011, when the Red Sox collapsed in September and reports surfaced of pitchers Jon Lester, John Lackey and Josh Beckett eating fried chicken and drinking beer in the clubhouse during a game, Epstein was done with the politics and drama of Boston. He needed a new challenge.

Two years earlier, the Ricketts family had purchased the Cubs, and they saw Epstein as their ideal executive. Epstein, having vanquished the Curse of the Bambino, saw Chicago and its Curse of the Billy Goat as his ideal destination. He signed a five-year contract, brought aboard Hoyer and Jason McLeod, his player-development maven in Boston, and set out to construct in Chicago what he had in Boston.

“He made sure I knew right away it wasn’t about one person,” Ricketts said. “It was about the organization. We talked about how you treat people and the right people will create success. It takes time. It won’t come overnight. He’s honest with everybody everywhere he goes.”

The Cubs won 61 games Epstein’s first year and 66 his second. To get to the top, they needed to bottom out first. They emptied out most of their best major league talent and focused on developing a core of young, dynamic everyday players. Some of it was skill, some luck. They saw superstar talent in Rizzo. They were fortunate Bryant slipped to them with the second pick in the 2013 draft. They swung a trade for shortstop Russell at the 2014 deadline. They dealt for a disappointing pitching prospect named Jake Arrieta and helped unlock his potential.

Every move – not just in on-field personnel but the construction of the computerized database they named Ivy, the recruitment of brilliant minds to fill the player-development and analytics department, the change in culture so desperately needed – pointed toward a future like the one that played out in Game 7. This was a plan, Epstein’s plan, executed in full.

“He’s also not in any way some kind of crazy dictator,” Ricketts said. “He just leads the right way. What I realized early on is the quantitative stuff is there, but that’s not a key. The key for him is hiring the right people and helping them get to the right decisions. And each of those decisions is what built this team.”

Following an 89-loss season in 2014, Epstein and Hoyer agreed: their cupboard, so barren when they arrived, was stocked enough to start acting like the big-market organization they were. They fired Rick Renteria, the manager they’d hired a year earlier, to open up the job for Maddon, who was available only because of an opt-out in his Rays contract that he exercised following the departure of their top executive, Andrew Friedman, to the Los Angeles Dodgers. And on the first day of free agency, they sent a custom-made DVD to free agent pitcher Jon Lester, whom they’d drafted in Boston and wanted to serve as the linchpin of Cubs rotations going forward.

It wasn’t an easy sell. Lester would need to take a leap of faith – to believe the baby Cubs were every bit as good as prospect mavens declared them. The San Francisco Giants, winners of three of the previous five World Series, wanted Lester, too, and offered him a longer contract with more money than the Cubs’ final offer of six years and $155 million.

Lester couldn’t shake the idea of winning in Chicago. The idea of being on the Cubs team that does it, being in the city when an inconceivable number of people cram the streets, appealed to him more than anything. He signed with the Cubs. They won 97 games last season. It was simply a prelude.

In the midst of the celebration Thursday morning, as players and families shuffled in between the clubhouse and the field, Hoyer ran into Lester.

“Seventy-three wins and you signed with us,” Hoyer said. “Might’ve been stupid, but it worked.”

“I’d say,” Lester said. “We won the World Series.”


Theo Epstein and Cubs owner Tom Ricketts embrace after the Cubs won the World Series. (Getty Images)
Theo Epstein and Cubs owner Tom Ricketts embrace after the Cubs won the World Series. (Getty Images)

Exactly three months before Halloween, Theo Epstein was so pissed off at himself he started to bang on street signs. It was July 31, the day before the trade deadline, and the St. Louis Cardinals were threatening to winnow the Cubs’ National League Central division lead, once 12½ games, to 5½. And Epstein thought it was all his fault.

A left-hander named Brian Matusz, like Arrieta a former Baltimore pitching prospect, started for the Cubs that night. Chicago was trying to build organizational depth and figured Matusz a safe risk, especially after he had pitched well at Triple-A. Matusz allowed a two-run homer in the first, second and third innings, and Epstein, hunkered down for days in trade talks, needed some fresh air. He and Hoyer decided to take a walk. They ended up going for miles – talking, self-flagellating and whacking signs out of frustration. Never again would he do this, put at risk the dynamic of the clubhouse Maddon spent so long building for a flight of fancy.

“I felt like I had personally cost the team a game in the pennant race,” Epstein said.

“He took it personally,” Hoyer said.

“I took it very personally,” Epstein said.

“We were too cute about it,” Hoyer said.

“We overthought it,” Epstein said.

In the eighth inning, Epstein headed down to the Cubs’ clubhouse, ready to own his mistake face to face with the players. He refused to run from his errors. If he wanted the respect of players, he needed to face them.

Then something happened. Chicago scored three runs in the ninth inning to tie Seattle. The Cubs didn’t allow a run for the next three innings. And in the bottom of the 12th, they won on a walk-off squeeze bunt by Jon Lester. And even though the team he assembled absolved him then the same way they did Chapman in Game 7, Epstein went up to the Cubs players after the game and promised: That will not happen again.

From that day on, the Cubs won 40 of 57 regular-season games. They cruised into the playoffs with 103 victories. They weathered a Game 3 loss at San Francisco in the division series and authored a staggering four-run ninth-inning comeback to eliminate the Giants. In the NLCS, they fell behind the Dodgers two games to one before ambushing them with three straight wins to reach the World Series for the first time since 1945.

After splitting the first two games in Cleveland, the Cubs headed home to $2,000 tickets and signs that said “It’s Gonna Happen” and the possibility of winning the World Series at home. Cleveland waylaid them in Games 3 and 4, and belief was suddenly in short supply. The Indians had three cracks at one win and a pitching-centric formula that had helped them run roughshod through Boston and Toronto in the American League playoffs. The Cubs had superior talent, yes, but short series do a mighty fine job of neutralizing that sort of advantage.

Nobody in the Cubs’ front office ever mistook Epstein for an optimist. Surly? Salty? Caustic? Certainly. Pragmatic? Realistic? Logical? Always. But optimistic? Optimism was for suckers. Epstein lives by four words: “We don’t know [expletive].” And optimism isn’t pure hope; it is hope with a dash of knowledge.

So when he showed up before Game 5 not with a smile on his face, necessary, but with words of encouragement – well, the Cubs’ front office, an incubator of counterintuitive thought, of valuing the rational over all, was wondering whether Epstein had gone mad. Theo? Feeling good? What the hell?

“I’m usually not positive,” Epstein said. “I’m not the one we rely on for positivity. I felt good. I felt like we could win.”

Part of it was Epstein’s natural desire for balance. If everyone else is up, he’s down. If everyone is down, he needs to be up. Good managers understand the value of the middle, and Epstein evermore draws his team there. More than that, though, he really did see a win in Game 5, when Lester was going on full rest against the Indians’ Trevor Bauer on three days’ rest, and in Game 6, with Arrieta against Josh Tomlin on short rest, and then Game 7, when anything could – and did – happen.

The beer on his clothes had dried by the eighth inning, when the Cubs handed a three-run lead to Chapman and he frittered it away within a matter of minutes. One second Epstein was getting congratulatory text messages. The next he was getting existential in his thoughts as he stared at a scoreboard that read Cubs 6, Indians 6.

“The fickle nature of life and baseball and the crazy business we’re in,” he said. “We threw 18 straight fastballs, and Davis yanked one down and in and we gave up a two-run homer and tied up the game. And you think five years’ worth of hundreds of people making thousands of sacrifices might’ve just gone for naught. I was really worried and concerned and upset.”

This is what Tom Ricketts sees, one of the many reasons why before the postseason began he handed Epstein a five-year contract worth a reported $50 million: He bears the burden for the entire organization. This job is not his. It’s Hoyer’s and McLeod’s. It’s Maddon’s. It’s Bryant’s and Rizzo’s and Lester’s and Arrieta’s. It’s the business and sales sides’. The Cubs are not a baseball team. They are an institution, and institutions require care and nurturing and responsibility.

It’s why, as the entire world wanted a piece of him, when his phone was blowing up and hundreds of text messages sat unanswered, when he was still too drunk on Champagne and high on Game 7 to have any real sense of where he was, Epstein gathered the baseball-operations staff that sits in a no-cubicle office every day to figure out how to do what they’d just done.

They wound their way through the crowded hall and into the dugout, where they were told, no, don’t go onto the field. It’s pouring. No one listened. They rushed to the pitcher’s mound, crowded together, Epstein in the middle of it all, and posed as a gang of photographers clicked their shutters. And then, at 2:05 in the morning, less than two hours after he’d won the World Series, Theo Epstein stood up and started to dance, and everyone around him did the same.


They knew Opening Day. Spring training had been great and all, but it was spring training, and anybody could look at the roster and say, yeah, the Cubs were the best team in baseball, but paper is just paper, and Opening Day is just one game, sure, but this was something different. The Los Angeles Angels, it turned out, were a bad baseball team, and yet the 9-0 shellacking the Cubs delivered them felt like something bigger.

“If their expressions and actions could talk,” Epstein said, “they would say, ‘Holy [expletive], that’s how good we can be.’ I can’t wait to do this 110 more times. It ended up being 113 more.”

What’s scary to him – what’s scary to all of baseball – is this may just be the beginning. The Cubs of Ernie Banks, of Billy Williams, of Ron Santo – the Loveable Losers – may become an anachronism. Nothing is guaranteed in baseball, not now, not ever, but the Cubs are still getting better. “This is a great team,” Epstein said. “Factor in the youth, and what we can become?”

The question was rhetorical, but it wasn’t far-fetched. The Cubs are young. They have money. The team is a destination for players drawn by the organization, the manager, the city, the prospect of a dynasty. Even if the next time isn’t quite like this one, a championship is a championship, and no team is better equipped over the next half-decade to win one than the Cubs.

This is what Rizzo dreamt. No, literally, he had a dream this week, when the Cubs were trailing, that they came back and won. He was partying. Cubs assistant GM Randy Bush was there. He didn’t want to wake up. When he did, Rizzo helped the Cubs adopt the Rocky theme that buoyed them before Game 5, another hokey Cubs trick in a line of effectively hokey Cubs tricks. Rizzo embodies the Cubs culture. Epstein, Hoyer and McLeod drafted him in Boston. Hoyer and McLeod, who went to the San Diego Padres before rejoining Epstein in Chicago, traded for Rizzo there. And he was among the first players they acquired in Chicago.

“I need a picture with you two,” Rizzo said when he ran into Epstein and Hoyer in the hall, which had thinned out.

They posed, Epstein on the left, Hoyer on the right, Rizzo in the middle.

“To San Diego!” Hoyer said.

“To Boston and San Diego!” Rizzo said. “To the dark days.”

“To the scouts who said he had a long swing,” Epstein said.

Photos snapped, Rizzo was off to join his teammates, his friends, someone else.

Though not before he turned around and looked at Epstein and Hoyer.

“Hey,” Rizzo said, “let’s come back and do it next year.”


The first part of the party was over. There would be the plane ride and the welcome home in Chicago and the parade as early as Friday and the offseason of feting and the rest of eternity, when if your credentials include member of the 2016 Chicago Cubs you’re every bit the Chicago royalty of Michael Jordan, Mike Ditka and Abe Froman. The celebration at Progressive Field, though, had to end at some point, and that point was around 3 a.m.

They were reminiscing about something that hadn’t even happened three hours earlier, and their lives were changing in real time. Ross and Hoyer compared unread text messages; Ross had 171, Hoyer 165. Shiraz Rehman, another assistant GM, proudly showed a picture of the tree in front of his house decorated with what must’ve been 50 rolls of toilet paper, courtesy of his friends and neighbors. This was just the beginning.

“Think this plane ride is gonna be fun?” Rizzo said.

The clubhouse began to empty for the 3:30 a.m. bus to the airport. Lester walked out the door with a plastic bag that held a dozen assorted cans of beer. He figured most of them would be gone by the time they landed in Chicago. Maddon wasn’t shy with his plans, either: “I’m just gonna drink a lot of Jack Daniels.”

All of this was surreal – the night, the month, the season. The Chicago Cubs won the World Series. Six words impossible to conceive of until they weren’t. The most oft-heard refrain inside the celebration was even simpler: “It happened.” The years of futile rooting, the faith during the teardown, the nausea the name Rajai Davis will forever provoke – it was for this.

Epstein left the clubhouse with Marie and Jack, who nodded in and out on his dad’s shoulder. “Long month,” Epstein said, as he walked toward the Cubs’ bus to join the rest of the World Series champions.

A few minutes earlier, Hoyer left the clubhouse with his wife, Merrill. He was holding the Commissioner’s Trophy. People in the hallway gawked. Some mustered the courage to approach Hoyer and ask for a selfie. The trophy had a Pied Piper effect. Everyone wanted to see it, touch it, follow it, pose with it. Hoyer obliged, then wove his way to the part of the stadium where it was just him and Merrill, Maddon and his wife, Jaye. They strode onto the bus. On its side was the name of the company that was renting the coach to the Cubs.

It said Champion.