How the Chicago Cubs Made World Series History

25 minute read

This extraordinary Game 7 was for Judy Caldow, a retired teacher who sits in Section 309, Row 14, Seat 10 of the Wrigley Field bleachers. She has been going to services at that chapel of a ballpark for 53 years, her faithful attendance marked by the scorecards from more than 3,000 games. “She’s like the goddess of the bleachers,” says Lisa Medo, a friend who sits a few seats over. Caldow, Cubs scarf covering her neck, was the first fan to burst through the centerfield gates after they opened a few hours before Game 3 of the World Series, the first Fall Classic game at Wrigley Field in 71 years. “Happy World Series!” she says while hugging a stream of ballpark ushers, security guards and cooks.

The bleacher regulars are a tight-knit group, some 200 strong, with a bond cemented by decades of unfailing devotion to one of the worst, most unlucky, possibly cursed teams in professional sports. The regulars show up to each other’s weddings, baby showers and funerals. “It sounds kind of crazy, I know,” says Caldow, 67, “but when some of us have issues, we’d rather talk to our ballpark family rather than our own family.”

Game 7 was for Bill Shannon, a retired machine tool company executive from Rockford, Ill., who sits in Section 310, Row 14, Seat 2. Shannon’s a 63-year bleacher regular who watched all three World Series games at Wrigley next to his son, Tim. When the Cleveland Indians took a 7-1 lead in Game 4, on their way to a 3-1 Series advantage that pushed Chicago to the brink of elimination, it was Bill who kept smiling, who refused to count the Cubs out. The starting pitching will carry them through, Bill insisted. This year really is the year.

“This is the one that means much more to me than the game,” says Shannon, 82. “It’s an opportunity to get together with a lot of friends, with my son. Why wouldn’t it be so important to me? Why shouldn’t it?”

Game 7 was for Scott Turow, a local boy who grew up rooting for his hometown team and kept at it after becoming a globe-trotting corporate lawyer and best-selling suspense novelist. Turow’s dad, a doctor who passed away 15 years ago, never showed his son much warmth. “He was just one of those guys whose tenderness for his children confused him,” says Turow, 67. Except when he took his son to Cubs games. “We were completely together in those moments,” he says. “It was one heart. It was the most complete communion we could enjoy.”

Since this improbable season took flight, when the Cubs stormed through baseball to win a Major League-best 103 games and kept it up through the playoffs, Turow has wondered what would happen if they actually won it all after 108 years of futility. “It’s character-building, when the Cubs stomp on your heart, and you have to put it back in your chest,” he says. “What will it be like for all of us not to live with the religion of suffering?”

He’s about to find out. The Cubs hung on to beat the Cleveland Indians, 8-7, in a spectacular 10-inning Game 7 Wednesday night, ending the most infamous drought in American pro sports: 108 years without a World Series. Chicago took a 6-3 lead into the bottom of the eighth before Cleveland got to Chicago’s weary closer, Ardolis Chapman, and tied the game at 6-6 on a two-run home run by Rajai Davis. But thanks to extra inning hits from two veterans, Ben Zobrist and Miguel Montero, Cubs fans can forget about 1908, the last year the Cubs won the World Series, the year the Model T made its debut. They can now scoff at the Curse of the Billy Goat, the supposed hex that a bar owner placed on the franchise in 1945 after his goat was kicked out of Wrigley. They can forgive the black cat that scurried in front of the Cubs dugout in 1969, foreshadowing a late-season collapse, and liberate Leon Durham, the first baseman whose costly error in the decisive Game 5 of the 1984 National League Championship Series helped send the Cubs home in October, yet again.

A special pardon should be extended to Steve Bartman, the bespectacled, headphone-wearing Cubs fan who made contact with a foul ball in Game 6 of the 2003 NLCS. The Cubs were five outs away from clinching the pennant: Cubs leftfielder Mosies Alou flipped out, thinking he would have caught the ball if not for Bartman’s interference. The Cubs collapsed and choked away the series. Bartman received death threats. He didn’t deserve abuse then. He should be welcomed back with a parade now.

Sure, the guys on the field and the coaches who directed them and the suits who orchestrated it all deserve plenty of credit, too. Boldface names like Bryant and Anthony Rizzo and Theo Epstein — the Cubs president and baseball prodigy who has ended World Series curses in Chicago and Boston — are now local legends. Hell, the entire roster, from shortstop Addison Russell to ace John Lester to the assistant to the assistant trainer, drinks for free in Chicago forever.

But once the national joke finally expired, and the Cubs finally ended their legendary losing streak – again, it actually did happen, that day has arrived – the players and front office were never going to shed the thickest tears, or call up the most vivid memories of lost loved ones, wishing they were here to see it. This win was always going to honor the fans, the ones who clung to their team like a cultural inheritance.

“Chicago’s always been the second city, never really been on top,” says Chris Hogan, 49. “The Cubs have given us this image as a loser. But Chicago can be on top of the world, we can feel it. It gives you goosebumps. I didn’t cry when my dad died. But I can’t help but get emotional now. He would have loved this.”

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This glorious day was no happy accident. The team’s transformation from laughingstock to World Series champions started in July of 2009, when the Tribune Co. sold 95% of the Cubs to the Ricketts family, which made their fortune founding online brokerage TD Ameritrade, for $845 million. The organization was floundering. “For years, the Tribune Co. used the Cubs as programming for its WGN superstation and Tribune newspapers,” says Jim Schein, clinical professor of strategy at Northwestern’s Kellogg School of Management, who has written a case study on the team. “Winning wasn’t paramount.”

The team’s facilities, from its Chicago home to its spring training camp in Arizona to the player development academy in the Dominican Republic, were the worst in baseball. Wrigley Field, the Ivy-walled ballpark opened in 1914, may be beloved, but it was also woefully out of date. Employees used cafeteria trays to protect the team’s computers servers from rain leaking through the ceiling. Many worked in construction trailers. “I don’t know what was more embarrassing,” Cubs chairman Tom Ricketts tells TIME. “The fact that half our people were in trailer offices, or that they had better offices than I did.”

The home clubhouse felt like a high school locker room. “We didn’t even have a batting cage,” says Ricketts. “Players had to hit off a batting tee to get loose and come in the game in the ninth inning. But before they put the ball on the tee, they would have to lower a board and a net, so when you hit the ball off the tee, you didn’t break a television. That’s not major league baseball. That’s crazy.”

The team poured $500 million into renovating Wrigley. “You can’t tell players you’re in a first-class organization, and give them third rate facilities,” says Ricketts. The overhaul led to sponsorship deals that rubbed many longtime fans the wrong way. Anheuser-Busch was made the team’s exclusive beer partner, pushing out Old Style, a regional staple affiliated with the team for 60 years. Billboards were added along the outfield wall, breaking up the tapestry of Ivy. This year, as part of a deal with Nuveen Investments, the Cubs erected a new 513-square-foot sign above the left field bleachers.

“You have to do stuff around the ballpark to generate revenues,” says Ricketts. “The team is a flow-through entity. All we do is we basically bring in all the money we can, pay all our fixed expenses and give the money to Theo to spend. Dollars don’t buy wins like they used to, but you want to give the baseball guys all the resources you can.”

In 2015, the team installed new video boards, including one in left field that’s 3,990 square-feet high. Owners of two rooftop buildings across the street from Wrigley unsuccessfully sued the Cubs, arguing that the right field board illegally blocked their view of the field (a perch from which they profited by turning their rooftops into ticketed venues). Video screens are standard at even big high school stadiums, yet many fans felt the boards and other Wrigley updates compromised tradition.

Winning, however, changes that tune. “I thought the signs and video boards were distasteful and disgusting,” says Matthew Furlin, 56, one of the ballhawks on Waveland Avenue who chase down home runs that sail over the bleachers and onto the city streets. He’s reclining on a rickshaw during Game 4, hoping to catch a moon shot; the new obstructions keep more balls in the park, cutting into his collection. “You don’t mess with a church,” Furlin says. “But you can’t argue with success. Well done. I take it all back.”

The Cubs lucked out when Epstein decided to leave Boston in 2011, after leading the team to its first World Series in 86 years in 2004 and another one three years later. Ricketts had just fired former general manager Jim Hendry, and was looking for someone to run the baseball operation. Ricketts says he surveyed about twenty owners, general managers, and agents around baseball, asking them who was the best fit for the Cubs. All but one had the same reply: Theo.

Ricketts and Epstein met for dinner in New York. “I didn’t really know him,” says Ricketts. “Here’s a guy, he’s like Cher or Bono. He’s just Theo. You don’t use the last name. He just has that profile. I just wanted to make sure he was someone I could communicate with and get along with. I was thinking I would meet someone quantitative, and maybe after winning so much, someone with a little bit of an attitude. I met the opposite. I met a very humble guy who made sure I understood it was about building a big organization filled with good people.”

Epstein signed on with the Cubs in October of 2011, and began overhauling the team. Among his first major acts: codifying the “Cubs Way” in a hefty development manual. “It comes from the way we hope our players play the game, and how we teach the game at the minor league level,” Epstein tells TIME. “So it can be really technical, like what foot to touch with on your way to second — I can’t tell you which one – or something more philosophical, like what characteristics we see in a high school kid that make us think he will be able to overcome the inevitable adversity that will face him in pro ball. If you have scouts that do a great job, dig really deep, he can find three examples of when a high school kid faced adversity on the field, three examples of when he faced adversity off the field, and how he responded. That might give you a bit better information to project how he might respond when all of a sudden he’s not the best player in pro ball. Does he want to quit and go home? Or does he want to figure out what his foundation is?”

Boston hired Epstein to run the Red Sox in 2003, when he was just 29. He became an early adopter of the advanced statistics revolution that came to be known as Moneyball after the Michael Lewis book. At a time when few were doing so, Epstein took a scientific approach to player evaluation and development, using advanced data and analytics to make decisions and find hidden value in players.

Those tactics have become widespread around the league, leading Epstein to reach deeper in Chicago. “In today’s landscape, it’s hard to get any kind of competitive advantage,” Epstein says. “It’s so flat out there. There’s so much publicly available information, let alone the common knowledge that the other 29 teams have as well. We’re not patting ourselves on the back for anything we do that might be super insightful or really thorough if we know the other teams are doing it too. It doesn’t get us ahead. So the rub lies in finding small insights, small things that you have first, that other teams don’t have.”

To that end, Epstein beefed up Chicago’s analytics operation. Tommy Hottovy, a former big league pitcher turned stats nerd, became the “run prevention coordinator,” charged with helping the team improve its defense. He travels with the squad, charting defensive positioning and pitch selections in the hopes of gleaning a small advantage that could lead to a hit saved here, a strike there and maybe, if it all adds up, another win. Hottovy works closely with catching instructor Mike Borzello – “the braintrust,” according to Cubs bullpen catcher Chad Noble – to prepare detailed scouting reports. Borzello, pitching coach Chris Bosio, and one of the team’s three catchers – Ross, Willson Contreras and Miguel Montero – hold a stream of meetings during games to work out kinks in the game plan. “This is something we’ve started to do in the last couple of years, because the information can be lost,” says Bosio.

Epstein also set out to train his players’ brain. The Cubs have a five-person mental skills team that offers mindfulness exercises, visualization drills, and meditation to all players throughout the organization. “The overriding philosophy is better humans make better players,” says Josh Lifrak, who runs the program. “Don’t let the moment get too large. Catch yourself thinking bad. That’s mindfulness. Not only knowledge, but action.”

The team has also taken up “neuroscouting,” a program Epstein started in Boston that, in essence, measures a hitter’s hand-eye coordination and reaction times to different pitches. Such tests aim to predict performance under pressure. Epstein guards details of the team’s neuroscience efforts as if they were state secrets. “I can’t give away that stuff,” Epstein says. “A long time ago we started this neuro program, and we were able to get a small advantage. It’s not a magic code, but some helpful information on how to evaluate young hitters, on how to help teach them along the way.”

When they hired Epstein, the Ricketts told fans that he would have to tear the team down to construct a winner. That’s never an easy sell, but the Cubs had little to lose. “Theo bought them credibility,” says former big league infielder Aaron Boone, now an ESPN analyst. “You need that to rebuild in a big market.”

During the first two years under Epstein, Chicago lost 101 and 96 games, respectively. “But the team was very transparent in what they were up to,” says David Axelrod, President Obama’s former senior political strategist and a devoted Cubs fan. “Everyone got invested in the project, got to know the kids they were drafting and followed their progression through the minor leagues.”

Among the young players the team acquired were three cogs of the championship team: first baseman Rizzo, 27, third baseman Bryant, 24, and shortstop Russell, 22. All three players had MVP-caliber seasons in 2016.

To construct a starting pitching staff, Epstein acquired both Jake Arietta and Hendricks via trades for spare parts. After washing out in Baltimore, Arietta revived his career in Chicago, winning the 2015 Cy Young Award. Hendricks, a Dartmouth graduate who was projected as a back of the rotation guy, had the lowest ERA in the majors this season. Epstein rounded out the trades with a few splashy veteran free agent signings, like inking ace Lester to a six-year, $155 million contract after the 2014 season, and signing outfielder Jason Heyward to an eight-year, $184 million contract. Heyward disappointed at the plate this season, but he was a stellar defender and also helped rally the club late in Game 7, calling a team meeting when a rain delay threatened to fracture their focus.

Perhaps most importantly, when Tampa Bay Rays manager Joe Maddon opted out of his contract after the 2014 season, the Cubs pounced. In his two seasons in Chicago, Maddon has led the Cubs to the National Championship series and now, the World Series title.

During the down years before Maddon’s arrival, Ricketts heard his share of gripes about the rebuilding process. You hired Epstein to lose 100 games? “Once in awhile, you’d meet someone who was frustrated,” says Ricketts. “I’d talk to them and just explain why we have to go about it in a certain way. I would joke about it. ‘Hey man, it’s been 105 years. What are you holding onto?’”


In the first at-bat of the deciding game, Cleveland ace Corey Kluber, who was trying to become the first pitcher in 48 years to win three starts in a World Series, left a 94 m.p.h. fastball over the fat part of the plate. Cubs center fielder Dexter Fowler connected, sending the ball over the outfield wall for the first ever leadoff home run in a World Series Game 7. Cleveland tied it 1-1 in the third, but Chicago caught Kluber again in the fourth: Bryant hustled home on a short sacrifice fly by Russell to center. Contreras doubled in another run. In the fifth, second baseman Baez hit another home run, knocking Kluber out of the game and giving Chicago a 4-1 advantage.

APTOPIX World Series Cubs Indians Baseball
Chicago Cubs' Dexter Fowler celebrates after a leadoff home run against the Cleveland Indians during the first inning of Game 7 of the Major League Baseball World Series Wednesday, Nov. 2, 2016, in Cleveland.Charlie Riedel—AP

The Cubs added another run that inning. And then Maddon made a controversial move: he took out Hendricks, who was cruising, after he issued a two-out walk. Lester, who hadn’t appeared in relief since 2007, came on and allowed the Indians to score two runs on a wild pitch. The decision looked foolish until the top of the sixth, when Ross, Lester’s go-to catcher who came into the game along with his pal, knocked a solo home run to center, extending Chicago’s lead to 6-3, and giving Maddon and the Cubs some cushion. Lester settled down, but Maddon again looked to his bullpen, pulling him for closer Aroldis Chapman with two outs in the eighth, and a man on first.

Before the game, Maddon said he regretting throwing Chapman in Game 6, a 9-3 Cubs blowout win. And it was clear Wednesday that Chapman was gassed. Brandon Guyer doubled and drove in a run, making it 6-4. Then Rajai Davis ripped a game-tying two-run home run, sending Progressive Field into pandemonium. In Wrigleyville, where thousands gathered to celebrate, stomachs were gutted yet again.

But the Cubs bounced back. Chapman, looking lost in the eighth, got out of the ninth, sending Game 7 into extra innings. After a short rain delay before the 10th, Kyle Schwarber, the young slugger who returned for the World Series from what was supposed to be a season-ending knee injury back in April, singled to lead things off and was replaced by pinch runner Albert Almora Jr. Bryant lofted a flyout to the centerfield wall; in a clever, and crucial, base running move, Almora Jr. tagged up to second, putting the go-ahead run in scoring position. After an intentional walk, veteran Ben Zobrist doubled to left, scoring Almora Jr. and giving the Cubs a 7-6 advantage. A Miguel Montero single added another insurance run.

Cleveland came within one run in the bottom of the 10th, but couldn’t make up the difference. And like that, the Chicago Cubs became World Series champions.


Game 7 was a rollicking capper to a historic season. After being swept in the 2015 National League championship series, Chicago began this year 27-8, baseball’s best start since the 1984 Detroit Tigers went 30-5 (Detroit also won the World Series that year). Aside from a rough patch right before the All-Star break, the Cubs cruised to 103 regular season wins, the best record in baseball.

The Cubs know from hexes, however. Over the past quarter century, regular season success has cursed postseason glory. Only four teams with baseball’s best record over that span went on to win the World Series. The Cubs flirted with potential disastrous early playoff exit in the National League Division Series. While leading the San Francisco Giants 2 games-to-1 in a best of five, Chicago trailed 5-2 going into the top of the ninth inning of Game 4. San Francisco had developed a habit of winning world championships in even years (2010, 2012, 2014). A Giants victory would have sent the series back to Chicago for a decisive fifth game. Wrigley’s confines are friendly. But Cubs fans would have rather gone for a February dip in Lake Michigan than have to suffer through winner-take-all duel in the early playoff rounds. The Cubs, however, rallied to score four ninth-inning runs to close out the series.

Chicago would face the Los Angeles Dodgers for the pennant. After falling behind 2-1 in the series, the Cubs reeled off three straight victories, clinching the league championship at Wrigley on a crisp Saturday night. With the Cubs up 5-0 in Game 6 and five outs from the NL championship, Hendricks surrendered a single. Five outs: that’s all the Cubs needed back in 2003 before the Bartman incident sent Chicago spiraling. Many Cubs fans dreaded this sign. An innocent single can beget another stunning collapse. “I thought. ‘Oh no! Oh no! Oh no!,” says Holly Swyers, an anthropologist at Lake Forest (Ill.) College and author of the 2010 book Wrigley Regulars: Finding Community In The Bleachers. “I’ll be OK. It’s not going to hurt as much as last time. But it will.”

The Dodgers, however, faded quietly. Chapman relieved Hendricks and induced double plays in the eighth and ninth innings to close out the series. Wrigley partied hard. For Cubs fans, just reaching the World Series was a monumental victory in itself. “It’s wonderful, but equally as strange,” said comedian Jeff Garlin in the days after the Cubs clinched the pennant and lost Game 1 of the World Series. “It kind of threw me for a …what’s it called? Don Draper had it happen in his life, everything was a…what’s the term I’m looking for, when your life just spins in a direction, you have no idea … you’re a writer, dammit help me man!! … Ah, ah, ah … oh it’s going to come to me.. ohhhhhh … your whole life just turns upside down, I’ll get the phrase … Ahhh, I got it! Existential crisis! I literally, I’m not even making this up, starting Saturday night, and through yesterday’s ballgame, I was approaching my work, approaching my marriage, approaching fatherhood differently. Everything sort of spun in a different way. Some for the good, some for the not good. It confused me. I’m not so confused anymore. By the way, existential crisis over.”

It almost wasn’t. Cleveland took a 3-1 series lead, and Chicago’s bats looked lifeless. Cleveland pitching held the Cubs to just two runs in their three wins. Yet even as the Cubs faced elimination, the clubhouse didn’t panic. “We’re in the World Series, what better place to be, right?,” said Ross after Chicago’s 7-2 Game 4 loss. “There are lot worse things. There are a lot of guys at home wishing they were down 3-1, going into a World Series game in Wrigley Field.”

“All we have to do is just chill, and have a little more fun,” said Montero. “That’s all.”

The Cubs were essentially channeling Maddon, Chicago’s impossibly chill manager. A sign hanging in their home locker room says “Don’t Let the Pressure Exceed the Pleasure.” This season he set up a strobe-light-equipped party room in Wrigley Field so the Cubs could celebrate home wins. After the Cubs held on for a 3-2 victory in Game 5 to send the series back to Cleveland, another locker room sign reminded Cubs players that on the team flight eastward, “Halloween costumes are encouraged.”

Maddon is known for his strategic acumen — though that rep may take a hit after Game 7 — and ability to get through to players. “During pregame workouts, or pregame batting practice, he’ll go up to guys and ask how they’re family is doing,” says Ken Ravizza, a Cubs mental skills consultant and longtime Maddon confidante. “Guys pick up on that. Athletes today have to know you care before they care about what you know.”

After the Cubs hired Maddon, Epstein dispatched him to Puerto Rico to chat with Baez, a first-round draft pick who hit just .169 upon reaching the majors in 2014. “He built trust with Javy,” says Epstein. “Javy’s a great guy, but he’s not quick to trust you. Joe went to his hometown, got to know him, went out of his way to show how he believed in him.” Baez was co-MVP, along with Lester, of the NLCS. “Joe has kind of deconstructed some of the norms you used to see in baseball, where young players are seen and not heard,” says Epstein. “He’s created an environment where players are rewarded for being themselves. As long as they prioritize winning they can have fun.”


After Game 7 finally ended, Scott Turow walked out to the backyard of his suburban Chicago home and let out a scream. It finally happened! he yelled at the top of his lungs. If only his dad were alive to see it. At least his son and grandsons did. “What is life going to be like without this incredible burden,” Turow says over the phone, as the Cubs are still spraying champagne in Cleveland.

Bill Shannon, the 63-year bleacher bum, spent the last few innings on his knees at home, praying for the Cubs to pull it out. “I don’t think I could have taken another inning,” he says. Bryant throwing to Rizzo for the last out, says Shannon, “was one of the greatest moments of my life. When you get to be my age, you don’t know if you’ve ever going to see it. I kept thinking of my all my friends at Wrigley, and so many that are gone. I feel privileged to have witnessed this. I felt like I was fighting with the Cubs every step of the way.”

As for Caldow, the goddess of the Wrigley bleachers? She watched Game 7 from Disney World with her daughter. Seems fitting. She said her half-century watching losing Cubs baseball was all worth it, just for this win. Once Chapman gave up the game-tying home run to Davis, she thought it was all over. Which made the victory that much sweeter. “Oh my goodness,” she says. “I need to let this sink in. Oh my goodness. Oh my God. Oh man.”

Correction: The original version of this story incorrectly described Game 4 of National League Division Series. The Cubs trailed the Giants 5-2 before scoring four runs in the ninth inning. The story also misstated Bill Shannon’s age in one reference. He is 82.

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