Anne Caprara knew she wanted to spend her life in politics when she was 13.

At Catholic school in Radnor, Pennsylvania — a suburb of Philadelphia — Caprara got her first taste after telling one of the nuns that it was unfair that only the boys got to play the candidates in the 1992 presidential race.

A small concession was made, and Caprara got to play Barbara Bush during a mock debate in the eighth grade.

“Honestly, I was hooked after that,” Caprara said. “I remember sitting next to Pat … who was the quarterback for the football team, and he was playing George Bush, and thinking ‘you’re not speaking up enough,’ so I did all the arguments, I debated the whole thing, and at the end of it I was like ‘yeah, this is what I want to do with the rest of my life.’”

Caprara — the oldest of five kids and an ardent Philadelphia Eagles fan — would go on to get a bachelor’s degree from American University in Washington, D.C., and a master’s from George Washington University. She worked her first campaign shortly thereafter for EMILY’s List out in the Second Congressional District of Oklahoma for a Native American woman running in the primary.

She lost that “uphill battle,” but the experience paid off.

How Caprara crafted the Pritzker win

Caprara, 39, was the campaign manager, and chief architect, behind Governor-elect J.B. Pritzker’s win Tuesday night. After his resounding victory, Pritzker tapped Caprara to serve as chief of staff for his administration.

Caprara has over a decade of experience in the political sphere. She has managed campaigns across the country and worked on Democratic gubernatorial, U.S. House, Senate, and, in 2016, presidential campaigns.

She was brought on to lead Pritzker’s campaign in March of 2017. She says the very first time she sat down with Pritzker one of the things they talked about was that in this day and age voters “value authenticity more than anything else” and having him traverse the state and meet people in small and large settings “was really key.”

“Working for somebody like J.B., who’s just a naturally talented candidate, what you really want to do is make sure that their skills are on full display throughout the course of the campaign,” Caprara said.

Anne Caprara talks to a staff member at the Pritzker Campaign headquarters in Chicago, Friday, November 9th, 2018. | James Foster/For the Sun-Times

Anne Caprara talks to a staff member at the Pritzker Campaign headquarters in Chicago, Friday, November 9th, 2018. | James Foster/For the Sun-Times

“It was always about putting J.B. and who he was — and when Juliana [Stratton] joined the ticket, her as well, because she’s just an incredibly authentic human, too — in front of voters at all times.”

The entire campaign was structured that way, Caprara said. Along with getting Pritzker and Stratton out in front of voters, Caprara also built up a sophisticated digital team and a huge field operation that included about 34 offices and 130 organizers.

Caprara shines at team building, say colleagues

Guy Cecil wasn’t surprised by the success of the campaign or how expansive it was.

He’s known Caprara since 2011. The two worked together at the Democratic Senatorial Campaign Committee before he recruited her to join him at Priorities USA, the Democratic Party’s largest super PAC and the primary political action committee supporting Hillary Clinton’s 2016 presidential campaign. Caprara was executive director of Priorities before becoming its senior advisor.

Cecil said he didn’t know if there is anyone else you’d want on your side when running a campaign. Caprara, he said, is “relentless in her pursuit of winning” and has a knack for providing a campaign with a sense of spirit and values “which is difficult to do when you’re under the day-to-day stress of a campaign.”

“I think in politics you have people that are good strategists, and then you have people that tend to be good tacticians, and Anne is one of the rare people that is both strategically and tactically incredibly smart,” Cecil said. “The most important thing I think is her ability to recruit and manage the strongest team possible and actually to get them all working together.”

Anne Caprara confers with a staff member at the Pritzker Campaign headquarters in Chicago, Friday, November 9th, 2018. | James Foster/For the Sun-Times

Anne Caprara confers with a staff member at the Pritzker Campaign headquarters in Chicago, Friday, November 9th, 2018. | James Foster/For the Sun-Times

At the Democratic Senatorial Campaign Committee, Caprara jumped into action during one unexpectedly tight race, building an on-the-ground team that helped Connecticut Democrat Chris Murphy win the 2012 Senate race.

For Pritzker, Caprara built a field operation that included people from the communities to “bring voters on board with you,” she said, which made the campaign, especially its senior staff, racially diverse and comprised of more women than men.

“I did that by design,” Caprara said. “I wanted people who came from different backgrounds and different places who brought different perspectives and made sure that when we tried to make decisions about the campaign that those folks were all getting listened to — that it wasn’t just me in a room with J.B. making a decision, but the group of us coming to a consensus about how we were going to handle something.”

Caprara says that she found the experience to be one of the most rewarding of her life and, in terms of the campaign, it made them better, she says.

Pritzker scandals tested Caprara

A series of scandals put the diversity of the staff to the test. Republican Gov. Bruce Rauner’s campaign ran ads featuring embarrassing wiretapped recordings of Pritzker talking to former Gov. Rod Blagojevich. In one, the two discuss the best candidate to fill former President Barack Obama’s Senate seat, and Pritzker makes disparaging remarks about leading African American politicians.

Then in October, the campaign was sued by 10 black and Latino workers who called it “a cesspool of racial discrimination and harassment.”  And less than two weeks before Election Day, two staffers were fired after appearing on social media in charcoal masks that bore a heavy resemblance to black face.

Caprara says that every campaign faces challenges and “in the modern day, the things that are out in the news, on social media, go through much less filters than they did in the past.” Campaigns have to be aware of that and they have to deal with it, she said.

And she insists the controversies should not reflect poorly on Pritzker or the campaign.

“With the Blagojevich tape and other things, we know who J.B. is in his heart, and the team — we wanted to work with him on how we were going to respond and how we were going to deal with that, and he took responsibility for the stuff he said and that’s all you can ask [of] somebody in this day and age,” Caprara said.

Governor Elect J.B. Pritzker's Chief of Staff Anne Caprara, at the Pritzker Campaign headquarters in Chicago, Friday, November 9th, 2018. | James Foster/For the Sun-Times

Governor-elect J.B. Pritzker’s Chief of Staff Anne Caprara, at the Pritzker Campaign headquarters in Chicago, Friday, November 9th, 2018. | James Foster/For the Sun-Times

“From a team perspective, dealing with all of these different challenges made us stronger, made us closer. We really trusted one another in terms of what advice we were giving, both to the candidate and to other people.”

A short break, then back to work

A few days after the election, Caprara said she was “elated, but exhausted.” She plans to go surfing in Costa Rica where she’ll spend about a week in the ocean, where no one can reach her and she can decompress by hanging out with surf friends who don’t follow politics.

Despite the upcoming downtime, Caprara said she’s looking forward to getting back to work for the state and for Pritzker. She called working with Pritzker and Stratton the “honor of her life.”

“I’m excited about the prospects of bringing new talent and old talent into the administration,” Caprara said. “Having a bright new day, I think, is going to be fun, interesting, hard at times but challenging in a really good way.”

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