Shumpert Caldwell was 14 when he first met Jim Kenney.
The then-city councilman came upon the teenager spray-painting graffiti on a South Philadelphia wall.
"Whoa, what are you doing?" Kenney recalls shouting before ordering Caldwell into his city car for a ride to Benjamin Franklin High School.
"I told the principal, 'He's mine,' " Kenney said in a recent interview. "'If he's not at school, let me know.' "
That intervention did not keep Caldwell from weaving for years between the street life and the straight and narrow, a journey that included a jail stint for selling drugs. But Kenney's persistence paid off. Caldwell, now 35, is married, on the right side of the law, and, with Kenney's help, an aide to City Council President Darrell L. Clarke.
"Without Jim, I would probably be one of the worst people out there, robbing, shooting people," Caldwell said, still seeming mystified by a stranger's actions 21 years ago. "To have somebody have your back, somebody who doesn't know you at all."
That improbable intersection, those who know Kenney say, offers a small window into the man who seeks to become the Democratic nominee for mayor of Philadelphia.
Friends describe a passionate, if at times intemperate, man, loyal to a fault, driven to do what he perceives is right.
Over his 23 years on Council, that meant fighting for domestic partnership rights for gay and lesbian couples, ending a city policy of detaining immigrants for possible federal deportation, and reducing penalties for small amounts of marijuana.
It has also meant taking some stances or uttering words he later reversed or regretted.
He supported school vouchers. He pushed bills to end aggressive panhandling and forbid the homeless from camping on sidewalks. He opposed a civilian board to review police actions, and complained to a reporter in 1997 that too many restrictions were put on police use of force.
"I mean, come on, you can't use flashlights, you can't use clubs on the head, you can't shoot anybody," he said. "What's next? Are we going to hand them feather dusters?"
Another time, he flippantly suggested that a double-murder defendant's injured hand should be amputated rather than surgically repaired at taxpayer expense.
If those comments ring familiar, it is because Kenney's mayoral rivals have made the most of them. His past positions have come under fire, particularly from State Sen. Anthony Hardy Williams and Nelson A. Diaz, who contend that Kenney is not the progressive candidate he portrays himself to be.
Kenney the candidate says he is embarrassed by some of his past inflammatory statements. He dismisses many of his less-than-liberal stands as the views of a younger man who needed time to evolve. Today, at 56, he criticizes police brutality, supports a civilian review board, and pledges to end stop-and-frisk.
"Have I evolved on my stances on law and order?" Kenney said. "Yes, because they weren't the right answers to the problem."
Former City Councilman Angel Ortiz, a liberal standard-bearer, offers testimony to Kenney's philosophical journey.
"In the beginning, Jimmy and I were on the opposite of everything," said Ortiz, who is backing Diaz for mayor in the May 19 primary. "There were times during debates he would call me a left-wing socialist. But he evolved and became more accommodating. I didn't have to endure those rants any more, and we became friends."
A former colleague who is less convinced is Bill Green, who served with Kenney on Council for years - and sparred with him for years - before being appointed to the School Reform Commission.
"I don't believe he is a true progressive," said Green, who is supporting state Sen. Anthony H. Williams in the mayor's race. He contends Kenney's stands on issues such as LGBT rights and reducing pot penalties represent nothing more than riskless "pandering" to narrow constituencies. "He is calling himself brave for supporting things that were already popular."
Then there are those who see Kenney as too closely tied to powerful names not on the ballot. Is his history too intertwined with that of his onetime mentor, former State Sen. Vincent J. Fumo? Would Mayor Kenney - as rival Williams asked at a debate this week - do favors for one of his most powerful current supporters, labor leader John "Johnny Doc" Dougherty?
No and no, Kenney says.
The talk about Fumo, who went to prison on corruption charges long after Kenney left his payroll, especially irks him. "That is another thing that cracks me up," he said. "I have not worked for the guy in 24 years. I have not spoke to him in seven. When am I my own guy and not somebody's boy?"
A firefighter's son
Kenney grew up in South Philadelphia, son of a firefighter. He went to parochial elementary school, St. Joseph Prep, and La Salle University.
He credits the Jesuit priests who taught at the Prep for instilling in him a drive for public service: "They helped show me that you are not truly happy until you were serving others."
Drawn to politics, he volunteered in college to work for Fumo, who was one of the most powerful political figures in Pennsylvania before his conviction in 2009.
Kenney was Fumo's chief of staff for a time. He had started at the lowest rung, doing constituent service work, such as guiding people through the bureaucratic maze and helping the less-savvy file financial aid applications.
A former Fumo aide who knew Kenney in those years says the work shaped his views of government.
"He began to believe it could help people," said the former staffer, who did not want to be publicly connected to his past with Fumo. "It should address wrongs and improve the lives of people."
Kenney said the job certainly honed his people skills: "It helped build me into a person who cared for others, who wanted to serve others, and who got a kick out of fixing other people's problems."
Critics, including Green, say Kenney should not be given a pass for his long and close relationship with Fumo, whose machinations and misdeeds are often seen as representing the worst in Philadelphia politics.
But Fumo's career was not all misdeeds, and Kenney's time working with him meant meeting constituencies he had never known growing up in his tight-knit Irish Catholic world in South Philadelphia. One was the gay and lesbian community.
Mark Segal, publisher of the Philadelphia Gay News and a supporter of Kenney's, remembers meeting the young aide to Fumo.
"He said to me: 'I went to a Jesuit school. We were taught how to accept people,' " Segal said. "It grew from there. It grew to the point where there was not a piece of LGBT legislation that Jim did not have his name on it."
It was not always easy for Kenney. He drew heat from the local Catholic Church and acquaintances for his support for a 1998 bill to extend partner benefits to gay city employees.
John Murphy, president of the Jokers - the Mummers club of which Kenney is a member - said some in the club questioned Kenney's actions.
"There were guys who were saying, he does not know what he is doing," Murphy said. "The overall majority of guys stood by him. Sometimes the right thing is the right thing."
Segal said he is taken by Kenney's lack of artifice.
"With Jim, you know what you are getting," he said. "No polls are being taken to see what position he should take. He is going to take the position he believes in."
And take it with a passion that at times turns to irascibility. He is known for dark moods and occasionally angry, cutting remarks to those who thwart his legislative agenda.
"A lot of friends," Segal recalled, "including me, said, 'Jim, control your temper.' "
Kenney dismisses such concerns.
"Do I get red-faced and angry sometimes?" he said. "Yes, because I'm frustrated about the pace of things, frustrated that people are not able to meet their potential, and it bothers me. The main reason I'm running, I want to see if I can pull those levers myself and make it happen."
The race has pushed Kenney's limits in other ways. Not a naturally gregarious man, he has had to learn the art of selling himself to strangers.
"I enjoy it now. I didn't before," he said. "I didn't like glad-handing. It is easier now that people have seen me on TV and come up to me. It has loosened up my inhibitions. I'm not as self-conscious or embarrassed."
Seen as a front-runner in the race, Kenney said he at times indulges in the luxury of looking past the primary and picturing himself in the mayor's office, negotiating the myriad issues that wind up there.
"There are really serious problems," he said. "I think, how would I handle this? How would I handle that? I'm starting to think about the elements of particular issues as they relate to municipal unions, the schools, racial issues. How do I navigate all of these things?
"I know I have the experience to do it, but I need to put very good people around me. The thing that you learn, if you are smart, is, you might be the mayor, you might be the boss, you are at everyone else's whim. You have to figure out how to get all those people on the same page."
That note of humility was struck earlier in the interview, when he told of still enjoying the ribbing he receives when in the company of the Jokers.
"The key is, you are not so important," he said. "You do an important job and have important responsibilities. But you are not any more important than anyone else."
James F. Kenney
Residence: South Philadelphia.
Family: Separated; son, Brendan, and daughter, Nora.
Education: St. Joseph's Preparatory School (1976); B.A., La Salle University, political science (1980).
Occupation: Former city councilman at large.
Campaign website: http://www.kenney2015.com
Career: Administrative assistant to State Sen. Vincent J. Fumo (D., Phila.), 1980-84; chief of staff to Fumo, 1984-92; city councilman at large, 1992-2015.