The Theo Factor: Epstein turns his vision into reality with Cubs

David Haugh
Chicago Tribune

Name the best sports executives in Chicago history.

George Halas tops many lists, but the founder and owner of the Bears fits more comfortably in our institutional memory as a coach, the job he did for 40 years.

Bill Veeck, the late White Sox owner, deserves consideration for his innovative ways, but the Sox never won a championship on his watch.

Jim Finks ran the Cubs and Bears, and he drafted many of the players who won Super Bowl XX after he resigned in 1982 when Halas hired coach Mike Ditka without consulting him.

Jerry Krause celebrated six championships as general manager of the Bulls, a distinction that finally earned him induction into the Basketball Hall of Fame last September, posthumously.

John McDonough spent 24 years in the Cubs front office, including two as team president, before leaving to become CEO of the Blackhawks, where he changed the culture and presided over three Stanley Cup titles.

Stan Bowman has been the Blackhawks general manager since 2009, but perception often unfairly minimizes his impact because he inherited a roster that already had Patrick Kane, Jonathan Toews and other core players on a team that would win three Cups in five years.

Then there is Theo Epstein, on loan from Boston, who has done enough in six years in Chicago to belong among our city's permanent collection. With a shot at being the best ever, Epstein is only 43, with four years remaining on a contract extension he signed after the 2016 season.

Already in the Age of Epstein, the Cubs have rid themselves of silly billy goat curses and Steve Bartman jinxes and other peripheral nonsense that no longer fits the franchise narrative. Under Epstein, the Cubs have gone from lovable losers to perennial winners after he systematically reprogrammed a front office and a fan base so that gradually the recognizable red "C" has come to symbolize excellence, not futility.

Some baseball historians will point to the Cubs hiring Joe Maddon in October 2014 as the moment credibility arrived at Clark and Addison. Others cite the free-agent signing of pitcher Jon Lester two months later as the key move.

But the origin of real change — the dawn of Theocracy — started when Epstein opened his mind to the idea of leaving Boston, where he won two World Series, for the Cubs. The day was one of several that stand out in a tenure that has included unprecedented failure followed by unparalleled success.

October 2011: Tom Ricketts knew Epstein only from reputation. The two had never met, despite running in similar baseball circles since the Ricketts family bought the team in 2009. On that day, Ricketts promised to do something he had dreamed about since the day he started cheering from the bleachers as a University of Chicago student: lead the Cubs to a World Series. Ricketts knew hiring Epstein, one of baseball's brightest executives who had just completed a messy divorce with the Red Sox, would bring that dream closer to reality.

They arranged to meet at Ricketts' apartment in New York to avoid the sports paparazzi in Chicago and Boston, where Epstein's every Starbucks visit might be chronicled. A lifetime Cubs fan, Ricketts feared the worst.

"I didn't know him and was just worried," Ricketts recalled. "I didn't want to bring someone in with a big ego or someone who didn't treat people well."

Those fears dissipated soon after they sat down. Epstein exuded humility and humor, intelligence and insight, basically everything Ricketts had hoped. Everything Epstein has delivered.

"We sat down and the first thing Theo said was, 'I don't know what you expect, but it's not just me, it's a whole bunch of people, a group that works hard together, starting with scouting, training and building up to the GM, so you have to have a great organization,'" Ricketts said. "That was the first thing he wanted me to know at our interview, and I pretty much knew right then he was the right guy for us."

The move legitimized the Ricketts regime more than any other.

Oct. 25, 2011: Day one of the Epstein era in Chicago began with bold talk of a World Series and big words, with reference to The Cubs Way, whatever that was. After hearing Epstein outline his goals, I remember thinking if predecessor Jim Hendry was old school, Epstein was private school. Epstein's first official day at Wrigley Field, where he was approachable enough to pose with a picture of super fan Ronnie "Woo Woo" Wickers, was hailed as the beginning of Cubbie Camelot. Looking back, it also was prescient.

"When we build that foundation for sustained success and it ultimately results in a World Series, it's going to be more than just a World Series," Epstein said during his introductory news conference. "It's going to (affect) a lot of people, Cubs fans and Cubs families for generations who waited and waited for a World Series."

This was before enduring three of the longest seasons in Cubs history. Before firing managers Dale Sveum and Rick Renteria. Before hiring Maddon and signing Lester. Before everything that had to happen happened, Epstein foreshadowed it.

"To me, baseball is better with tradition," Epstein said that day. "Baseball is better with history. Baseball is better with fans who care. Baseball is better in ballparks like this. Baseball is better during the day. And baseball is best of all when you win. That, ultimately, is why I'm here today."

February 2013: The 197 losses the Cubs suffered in Epstein's first two seasons — the worst consecutive seasons in franchise history — were by design, a plan Epstein acknowledged one day at the team's spring training facility in Mesa, Ariz. Those were the days when pragmatism in the front office always mattered more than any punishment inflicted on the field.

"What I want to avoid is the middle ground," Epstein explained matter-of-factly. "It'd be nice to make the playoffs or get a protected draft pick (awarded the bottom nine teams). We're not hiding that. There's no glory in 78 wins instead of 73. Who cares?

"We're going to see where we are and take a real cold assessment in the middle of the season. If we have a legitimate chance to push for a playoff spot, then 2013 can become our primary focus. If we think a playoff spot's not in the cards, there will be no concern for appearances or cosmetics whatsoever. We'll continue to address our future and trade off some pieces that would keep us respectable."

Five months later, on July 2, 2013, executing the strategy Epstein described months earlier in Arizona, the Cubs flipped starting pitcher Scott Feldman and backup catcher Steve Clevenger to the Orioles for two struggling pitchers, reliever Pedro Strop and a 27-year-old right-hander whom they immediately assigned to Triple-A Iowa. His name was Jake Arrieta.

"I don't think this team improves by trading Scott Feldman," then-Cubs pitcher Jeff Samardzija said of the deal.

Obviously, Epstein knew better.

November 2013: Imagine inviting Epstein to an event on the night of a World Series game. What now seems unthinkable after three straight NLCS appearances happened just four years ago when the esteemed Economic Club of Chicago put the Cubs president on the agenda. The presumption of availability was noted by Epstein, who dazzled the 800 local movers and shakers with his detailed outline of player development and better times.

Patience with Epstein's plan had begun to wear thin in some parts of town, creating an ongoing debate whether to believe in it or expect more of the same from the Cubs. "Stop telling people what your plan is, Theo. Start showing them," is what I wrote in the Chicago Tribune that winter.

In 2014, the Cubs surprised people by going 73-89 under Renteria as Anthony Rizzo, a favorite of Epstein's from their days in the Red Sox organization, hit 32 home runs and Arrieta went 10-5. The Cubs exceeded expectations that were as low as Epstein admitted they should be after a quiet winter in which the team made its biggest splash by introducing the mascot "Clark the Cub."

"If I was a fan of the Chicago Cubs following the offseason, I would have hoped for more this winter, honestly. I'm not going to hide the ball from you," Epstein said before spring training opened in 2014.

That June, Epstein raised eyebrows by trusting Cubs scouts and selecting a slugging catcher from Indiana with the fourth pick of the draft: Kyle Schwarber.

Oct. 13, 2015: This was the first landmark moment Epstein made possible, a home celebration of a postseason series victory. Never before had that happened at Wrigley Field, not until the Cubs closed out the rival Cardinals 6-4 in Game 4 of the NLDS. This was the series of the Schwarbomb that landed atop the video board in right field and the season of the Arrieta excellence, two players who symbolized the Epstein influence as much as any. This was a team bolstered by Kris Bryant, the talented No. 1 draft pick, and Jon Lester, the transformative free-agent signing. On the field, amid the giddiness, Epstein understood the significance of the step the Cubs had just taken toward becoming perennial champions.

"We beat the Cardinals — I mean, these are like older brothers who've been kicking sand in our face for 100 years,'' Epstein said that night, comparing the Cubs' breakthrough moment with his Red Sox past. "There's a lot of similarities to when we knocked off the Yankees in '04. That one put us in the World Series. This one just gives us a nice date on Saturday."

The Cubs would get swept by the Mets in the NLCS, but the message was clear: Epstein had his team on the brink of a World Series title quicker than everyone expected — except perhaps him.

Nov. 2, 2016: Epstein had stood here before, on top of the baseball world, but this view was different. This was unique. This was the Cubs, the most futile organization in all of sports that he had resurrected in five years. Epstein had help bringing the organization its first World Series championship since 1908, which he took great pains to acknowledge, but the moment generations of Cubs fans doubted ever would happen started the day he met Ricketts.

"I want to thank everyone who has ever put on a Cubs uniform and anyone who has ever rooted for the Cubs," Epstein said as the champagne sprayed in the Cubs clubhouse after an epic Game 7.

Around Epstein, players he shrewdly brought to the Cubs to make it all possible — shut-down closer Aroldis Chapman, speechmaker outfielder Jason Heyward, Rizzo, Bryant, Schwarber, Lester, Arrieta, et al. — celebrated like Little Leaguers. This was the joy Epstein envisioned, his promise fulfilled.

"It has been 108 years of love and support and patience waiting for a team like this to make it happen on a night like this," Epstein said. "You guys are all world champions tonight. I couldn't be more happy for you."

Eventually, Epstein turned his attention to the people who don't wear jerseys, the hard-working, anonymous folks he valued so much; the scouts, the analysts, the secretaries, the young executives trying to emulate him. Finally, Epstein indulged in a selfish moment.

"I'm relinquishing my presidential duties," Epstein announced, voicing plans for a monthlong bender. "Wake me up for the winter meetings."

It only seemed like a dream.

dhaugh@chicagotribune.com

Twitter @DavidHaugh

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