Rahm Emanuel on his triumphs and failures in Chicago

Emanuel takes “Nightline” through his hometown and looks back at his achievements as well as the issues for which he was criticized in the city.
7:06 | 02/28/20

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Transcript for Rahm Emanuel on his triumphs and failures in Chicago
You can see down town from here. Reporter: For Rahm Emmanuel, the former mayor of Chicago, this library. How you doin', more important. Nice to see you. Lookin' good. Reporter: These people in Chicago's little Italy neighborhood. Miss you, miss you. Reporter: All part of his legacy. I take it you enjoy it. Yeah,'s people. Reporter: He's had a long career in politics, probably best known as president Obama's chief of staff. He's lass also served as six years in congress. To me, it's home. When you know you've found home, and you can't let go, that's where you always come back. Reporter: He served two terms and was the city's first jewish mayor. His grandfather was known as big what would your grandfather say about this time running this city that you both love. I try to not cry while talking about grandpa. One is that I put myself out there. You believe in something, put it on the table. Reporter: What would he be disappointed by? He'd be disappointed about poverty that we didn't get all those done. Reporter: He muses on grandfather's impact and his time in politics in his new book titled "The nation city, why mayors are now running the world", especially now as national politics both home and abroad have become so contentious. I had no idea that by 2020 the prime minister of England would be the former mayor of London. Bloomberg, buttigieg, Sanders, all mayors, more now running than anytime in 100 years. Anything you think about government as how it really impacts the way you go about live, work and play, is it Washington? It's pretty much local government. Reporter: Emmanuel's own term as mayor was filled with highs and lows. By the numbers, you had many successes as mayor. But the Chicago sun times op Ed gave you an F for collaboration. Why did that happen? Because when I locked and loaded on something and I thought it was important, and then basically pursued it to get it done. Reporter: You're not bothered by having enemies. What garnered the enemies? Reporter: A little more than a year into his first term as mayor, Chicago public teachers staged a strike, the first in nearly 25 years. Eventually, Emmanuel achieved his objective of lengthening the school day. There have been 500 homicides this year. Reporter: While in office, Chicago witnessed two of the bloodiest years in its history, the murder rate eventually going back down. But it was the 2014 police shooting of la Kwan McDonald that took the biggest toll on his mayorship. With accusations of a coverup by his administration and police department, after Emmanuel's office initially resisted releasing video of the shooting. I said all along, and I want to repeat, the reforms are to be effective and lasting, it needs to be done with police and not to police. Reporter: An inspector general report did not implicate his office in the coverup. Why did you fight to have the video kept private? Every city, entity, state, when they're investigating something they hold all the investigation material until it's done. Chicago's no different. A long practice, but it illustrates all the levels of distrust. Reporter: Did you make mistake? Oh, yeah. Reporter: 2018 Emmanuel announced he would not serve another term. Your successor said it was because you couldn't win. That's all hypothetical. I've never lost an election. I will never forget the honor it has been to serve alongside you, the people of Chicago. Reporter: Though his chapter as mayor is over, his transition to author and pundit swift. Since July of 2019, a contributor here at ABC news. He's never been afraid to lend his opinion on the race for the white house I'll say one thing about Bernie Sanders. His playbook is no different than Donald Trump's. Reporter: On this day, he shut the pundit image and wants to show us his hometown his way. When Bloomberg was in our town -- Reporter: While Rahm Emmanuel earned his combatant, hardscrabble reputation, we found a man at peace with himself. Very much in love with his city, and dare we say, a softer side. They're running' hundreds of people through here every day. The school's doing well. Reporter: Spearheading a partnership with Chicago local schools to build a trade facility. We can see kids that can see all the buildings going up. It represents power, opportunity, the future. You keep the cubs hat. How long have you been in this session? In is the third week right now. What made you decide? The jobs are here. The training. If they work it right. If I'm to ask, what's the Five years from now, you'll be making $45 an hour. Reporter: Next stop, marianos. What are you running for? Nothing. I ain't running' for nothing! Reporter: A grocery store built in the side of the Ida B. Wells. This was an inequity. Is it different today? Are there eight grocers in neighborhoods that didn't exist before? Reporter: And off to the train. One of the things critics say about you is they call you mayor 1%. Mm-hm. Reporter: That you cared more about what happened downtown, and oh, by the way, to the other communities. Nobody in the 1% cared about the free community college, raising the minimum wage. I understand the criticism. I'm proud of the fact that we kept the revenue growing so I could invest it. Reporter: When I read your book, it reminded me of every book I had read by someone Mo was planning to run for president. Then I'd be the first one to ever run with a second wife. So no. Here's the deal. I've gone to work for two great presidents. I have no interest in running for that job. I have a very good interest in making sure there's a democratic president but no interest in running for president. Reporter: From his immigrant grandparents, today Rahm Emmanuel, his family, his city, manifestation of what's possible. Complicated, combative, some may question portions of his record but not his love for his city or his efforts T make his ancestors proud and his hometown Bert. Chicago has a pull on my heart, my soul. It's where my family start. I really do. I think it's the best city. And next, bringing black

This transcript has been automatically generated and may not be 100% accurate.

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