KANSAS CITY, Mo. (AP) — Sixteen-year-old Sylvester James Jr. was set on taking Ann Brennan to his junior prom at Bishop Hogan High in the spring of 1968. The Notre Dame de Sion sophomore, whom he met at one of his rock band's shows, was cute, lively, "a great girl," in his words.

She was also white, and the daughter of Kansas City Councilman Frank Brennan. James didn't want any drama in pulling up to her home. So "Syl," as friends knew him then, handed over his tuxedo to a white classmate and asked him to pick her up.

"I didn't want her to have repercussions. I didn't want to have repercussions," he told The Kansas City Star .

Nearly a half-century after that prom night, Sly James still negotiates life in a divided city.

As he approaches the final year of a mayoralty filled with brick-and-mortar trophies like a new hotel and airport terminal, his agenda includes a much harder-to-build bridge: one across the city's racial divides. Later this year, James said, he plans to introduce a new initiative to promote racial understanding and equity.

James' last-mile push is deeply linked to his personal story. Much of it has not been told publicly before, and few realize the extent to which he was shaped as a youth on both sides of the city's racial lines.

Like former President Barack Obama, whose white Kansas mother and grandfather left a lasting influence, young Sly James forged early bonds with white adults who offered shelter, direction and "an opportunity for me to get a very early glimpse of what society and America was like."

Much has changed since the spring of 1968, when Kansas City was convulsed by rioting in the wake of Martin Luther King's murder. Yet by multiple measures, the city remains one of the nation's most racially and economically segregated.

"Turn around," he asked a recent gathering of white congregants at All Souls Unitarian Universalist Church in Midtown. It's an exercise he's led countless times in public appearances.

"Who's not here? Who's not here?"

Answer: people who look like Sly James.

"We need to be intentional about making sure everybody has a seat at the table. ...I know the people in this city and I know they have a good heart," he told church members. "But old habits are hard to break, and if you want to break them you've got to set a course."

James knows he can't single-handedly remediate damage from decades of racially discriminatory government policies and personal prejudice. But he's used the power he has to make diverse appointments to boards and commissions, raise third-graders' reading skills and improve digital equity for low income residents.

He's also made himself the message. He said he has walked out of meetings downtown and in other centers of municipal power — he won't say which — where his is the only face of color.

"I've told people until you guys find some age differences, some gender differences, some color differences, I'm not coming back," he said.

As with Obama, James' early cross-racial relationships and success in a white-dominated world have bred suspicion and criticism that too much of his political and financial capital has gone to big-ticket development downtown and elsewhere.

"You're never black enough for people who think everything you ought to do in political office has to be tinged black," said James. "And you're always too black for people who think everything you do in political office is tinged black. I don't listen to or pay any attention to either. ...White people don't have a clue about the history of African Americans in this country and the vestiges of slavery. And I don't think most African Americans have understood that although those vestiges are still there, we have the power to change our own existence. We're still struggling with all of that stuff."

All of this informs his desire to leave behind a city more committed to diversity and inclusion.

The details of the new initiative remain under wraps.

But at the heart of James' story is his formative struggle as a teenager in the late 1960s. It is about a powerful father, a passion for music, and "a confused 16-year-old black kid from a weird existence" who made a life-altering jump over a fence.

"The one conclusion I don't want you to draw is that somehow there was a villain in this," James said in an interview in his City Hall office earlier this year.

By that he meant his father. Sylvester James Sr. was a Marine mess sergeant, boxer and, later in life, a self-made business success. For years he worked two jobs: chef at the Black Angus and a janitor cleaning office buildings at night.

"He was a mentor in a very silent and powerful way," the mayor told Father Justin Matthews, executive director of Reconciliation Services, an east side non-profit, in an interview published on its web site last year. "Just watching him struggling in life and eventually succeeding, watching him maintain a strong sense of self and his own identity when he succeeded was very powerful. He was a direct and simple man with a lot of character and dignity."

On one level, the tensions with his father, what James called "a test of wills," were the usual push-and-pull between generations. But in the upheaval of the late 1960s, nothing was the usual.

Sylvester James Sr. brooked no dissent in his two-bedroom bungalow where he raised his family with James' stepmother, Melva, a keypunch operator at the IRS.

Young Sylvester's birth mother was "barely present," the mayor said.

On Montgall, James shared a bedroom with his younger brothers, LaVance and LaFrance. When they misbehaved he was punished, as the one responsible for those under him.

"My old man was a tough guy. He was hardcore Marine," James said. "When my father said something, that was the way it was going to be."

He also gave his sons bitter early lessons about the price of being a black man in America. When Sylvester James Sr. won $25,000 for his steak butter recipe in a contest sponsored by Del Monte, he used some of the cash to buy an old Rolls Royce.

"Every time he was in that car he got stopped by the police. Every single time," James said. "It was never, 'Do you know how fast you were going?' It was always like, 'Is this your car?' And that's where I think he was most instrumental in our lives. He showed us how to deal with it, and deal with it with dignity. ...It cracks me up when I hear white men talking about how discriminated against they are. You have no friggin' idea what you're talking about."

More than anything, Sylvester and Melva wanted a good education for their kids. James' Baptist parents converted him to Catholicism and sent him to parochial schools. It was his first portal into the white world.

For a time, James was the only black student at Bishop Hogan and became its first African-American graduate. Friends said his personality also made him stand out.

"He had no fear," said Chipp Tate, the friend who picked up Ann Brennan on prom night. "And he was funny. He shows up and starts editorializing and commenting on what the teacher would say."

His life spun in a new direction sophomore year with the arrival of Tom Cassidy, a kid from Philadelphia who had formed a band with some friends at Southwest High School.

Before James started hanging out with the Amelia Earhart Memorial Flying Band, the group was "a bunch of white kids doing the blues," said band mate Tate. With James as lead singer, it turned into something more.

The band, later known as Manchester Trafficway, quickly became "the core of my existence," James said, with his white band mates his new brothers. They played a mix of music that crisscrossed the racial and commercial landscape: Motown, Hendrix, Zappa, Cream and the Buffalo Springfield to name some.

The band came together at a rich musical moment in late 1960s-early-1970s Kansas City, when the Vanguard Coffee House, the Cowtown Ballroom and other venues were thriving. There were free Sunday concerts in Volker Park, and battles of the bands at Catholic Youth Organization dances.

They started making good money, even acquiring a booking agent who came up with surplus dress blue Air Force jackets to go with the original aeronautical name.

"This is the HAPPENING SOUND!" trumpeted a promotional flier with their photo.

Ann Brennan first saw James at one of his concerts.

"A great singer, charming, a nice guy. We loved to dance," said Brennan, now a business consultant in Chicago.

She realized they "raised eyebrows" as an interracial couple, but didn't think her parents objected. Frank Brennan was a moderate Republican with a reputation as a conciliator who spent several days on the East Side following the 1968 riots.

James said that while her father struck him as "a cool guy" he didn't want to run the risk of a scene on prom night.

"It's one thing to engage with (black) people on a business or political level," he said. "It's another thing to see them dating your daughter."

Some of the band's audiences were not happy to discover that its lead singer was black, either. One appearance in Blue Springs ended with a police escort out of town. Band mates said James was unfazed.

"He was never one to panic over anything," said guitarist Chris Immele.

A scarier moment came as James headed home from an after-school job during the riot-induced curfew in April 1968. Turning the corner of 44th and Prospect, he drove straight into a National Guard checkpoint. The sky lit up with flood lights, and James was forced out of the car and onto the pavement.

As his relationship with the band deepened, James found himself increasingly stretched across two worlds, white and black, neither of which felt completely like home.

"It was awkward and sometimes I didn't know where I fit," he said.

Back on Montgall, he delivered The Kansas City Call on his bike and hung with friends and family, some deeply wary of the white world. The whole bifurcated experience left him feeling, he said, "like an oddball."

The dissonance took its toll. In the fall of 1968, he made a split-second decision that opened another path across the city's racial divide.

The elder James, a huge football fan, had arranged for a family outing to a Chiefs game. They were about to leave when the phone rang.

It was great news: The band had a chance to open for Jefferson Airplane, which was booked to play Memorial Hall in Kansas City, Kansas, that May. But they had an hour to get to the audition. Without their lead singer, James knew, there was no chance to land the gig.

A jazz lover who thought his son's music was "noise," Sylvester James said no, he was going to the game. The young James would have to choose between his band mate-brothers and his family.

He described what happened next to reporter Katy Bergen last year on The Beer Hour, one of The Star's Facebook Live productions.

"So we walked out to the car and I said, 'Oh, I forgot something.' Went back into the house, got my sweatshirt, got my school books, whatever I could put in my pockets and out the back door, over the fence and I was gone. I left home at that point. It was that serious. So I didn't go back home for five years. ... Don't regret a minute of it."

James jumped the fence into what he called "a kind of benign homelessness."

He had money — from the band and part time jobs, earnings his parents had forced him to save. It was enough to pay the tuition at Hogan and get by. He stitched together a patchwork of places to crash: friends, friends of friends, couches in band mates' homes. When the weather was good, he'd spend evenings with teens who congregated on the steps of the Nelson Gallery.

One of them was Anne Lund, a white student at Loretto Academy, who found James to be "just the sweetest person, a good listener" with a singing voice "like an angel." Also troubled.

She brought him home to Waldo where he met her two sisters and Anne's mother, Diane, a child psychologist at the Rainbow Mental Health Facility, then an inpatient unit of Osawatomie State Hospital. She became a formidable presence in his young life.

"Not exactly June Cleaver," as Anne Lund described her. A free spirit with a mouth like a sailor, "Meemaw," as she was known, made James a de facto family member — and patient.

Dinners stretched into impassioned late-night conversations between the therapist and the homeless teenager.

Asked what they talked about, James said: "Everything that a child psychologist would talk to a confused black kid from a weird existence about," he said. "Whenever I wanted to scream she let me scream. When I needed a hug she gave me a hug. She was a surrogate mother in a lot of ways."

"It was just him and her," Anne Lund recalled. "He showed up any time day or night and he'd be sitting on the wooden stool in the kitchen, and it would go on for hours. She just took hold of him and fulfilled something he needed at the time."

In 1980, when James graduated from Rockhurst College, Lund's husband, Bill, gave him the kitchen stool with a brass plate attached. It said, "Lest You Forget."

One of James' issues might have been drugs. He said his experimentation was not out of line with most of his peers. But it eventually brought him together with another influential white adult, lawyer Austin Shute.

Shute was a legal maverick. As a young assistant Jackson County prosecutor in the late 1950s, he was fired for alleging links between organized crime and local law enforcement. Later he was the go-to defense attorney for Kansas City's counterculture, with a client list that included the local Black Panthers and their leader, Pete O'Neal. In the 1990s, he represented former Royals star Willie Aikens when he faced federal drug charges.

He also worked with at-risk kids, and at some point his apartment became one of James' rotating crash pads. This one might have had a little extra allure. Among the other guests was a Playboy Bunny the bachelor Shute was dating.

Shute ran an anti-drug group called Project Pepperland that brought young speakers to schools and churches to talk about their drug use. A May 1969 story in the Lawrence Journal-World described James and band mate Immele as part of "a group of former drug addicts" who met with students at Lawrence High School.

According to the article, James "explained that he started on drugs because of curiosity from reading the newspaper. His friends who were using then told him how cool it was and like most people he started on marijuana and worked up to acid, speed and other things."

Fifty years later, James downplays his chemical explorations.

"It wasn't like I needed to go into rehab," he said. "I experimented like everyone else. But I did believe Austin when he said it was a trip to nowhere. I bought into what he was preaching and agreed to work on it."

Perhaps just as significant, Shute was the first lawyer James had ever met. He was fascinated when Shute talked about his cases and the life he'd made for himself in the law.

"Austin was a huge influence," James said. "Knowing him convinced me that I wanted to be a lawyer."

Life came at James fast after he graduated from Hogan in the spring of 1969. The band and part time jobs brought in enough money to rent his own place in Westport. Sometime during this period, "Syl" morphed into the hipper "Sly."

By October 1970 he was married with his first child. His wife, Karen Nelson, was a friend of Anne Lund's, who described her as "light blonde hair, big blue eyes, gorgeous." In spring 1971, the draft board called.

Although James was still estranged from his family, his father loomed prominently in the decision to enlist in the Marines. He'd heard about them from the ex-mess sergeant his entire life.

"I needed to prove I could do something that our father had drilled into our heads as extremely harsh and difficult," he said. And besides, the Marines had "the coolest uniforms."

He said he enlisted because waiting for the draft would have increased his chances of going to Vietnam. The 13-week boot camp in San Diego that began his four-year hitch was "the biggest physical and psychological challenge of my life up to that point."

When he finished, he regarded it as his greatest success. His deep identification with the Marines surfaces on social media, when he urges followers to "stay frosty," a jarhead admonition to remain cool and alert no matter what happens.

Looking back, James said the diversity of his early years helped prepare him for the culture of the Marines.

"You don't have a choice about who is in the bunk next to you. And they brook with no bullshit about race," he said. "When you're in a situation where you're going to Vietnam to fight and die, the last thing you're worried about is whether the guy who's going to be in your platoon or fire squad is black, white, purple, Jewish or green. You (care) about whether or not they can shoot and will they watch your back."

With the war winding down, James was able to do his hitch as an MP in Japan, the Philippines and California, where a second son (and future Marine), Malik, was born in 1973. But the marriage ended in 1975.

Six years later, he married another white woman, Licia Clifton, whom he had met as an undergrad at Rockhurst. She's now an adjunct art history professor at UMKC. They had two children, son Kyle and daughter Aja, named for the 1977 album by Steely Dan, one of his favorite groups.

That both of his wives have been white is of no significance, James said.

"Who do you marry? Who do you date? The women around you. And since I didn't have a huge hang up about the black and white (differences) it really didn't matter."

James reconciled with his father before he deployed overseas, a reunion made easier by the presence of grandchildren. Before his death in 1996, his father's maintenance and food service business employed more than 200 people in four states. The elder James had also become a Republican.

"We kind of slid back into it," his son said of their relationship. "We didn't really have a huge discussion about anything that had happened." One thing James did learn from his father: Diane Lund had kept the family informed about his safety and whereabouts as he bounced from couch to couch.

No handful of years can completely determine the path of a life. There were other mentors and milestones as James moved from law firm associate to accomplished trial lawyer to two-term mayor.

But James's late teens instilled a belief that racial divides can be narrowed by personal relationships.

"I respect that time," he said. "I was fortunate to have those experiences at an early age. They helped me learn to get along. It's just that simple. ...It was the best friggin' thing that ever happened to me."

Can those early years make a difference now, as James tries to lift levels of trust and understanding between races in the autumn of his mayoralty?

He sounds as if he wants to find out.

___

Information from: The Kansas City Star, http://www.kcstar.com