It was a packed May weekend for Charlie Humphrey, with three art openings in 24 hours.

First, he made the rounds at "Glass & Steel: Art Transcends Industry" at the Pittsburgh Glass Center in Garfield, where he's currently in charge. The next evening he went to the 2008 Biennial at the Pittsburgh Center for the Arts in Shadyside, where he has been executive director since 2004. Then he zipped over to Oakland for the related Biennial at Pittsburgh Filmmakers, his baby since 1992.

There were bigger, more prestigious events that weekend -- the International opening at the Carnegie Museum of Art and a party at The Andy Warhol Museum, where he's on the board -- but Humphrey seemed content in these more intimate spaces, chatting and wise-cracking with artists, visitors and staff.

A casual observer wouldn't pick him out as an executive. With his long, lanky frame and characteristic jeans and T-shirt, he could be anyone.

But Humphrey is not just anyone. He's a fourth-generation scion of Pittsburgh's industrial wealth whose unorthodox upbringing far from the family fold was shadowed by his mother's alcoholism. As a result, he grew up straddling the line between insider and outsider. That, in turn, may have made him uniquely suited for the role he has assumed -- using his skills and his access to Pittsburgh's old-money foundations (Heinz, R.K. Mellon, Hillman, McCune, Pittsburgh) in the service of small, independent arts groups that give the city color and spice.

Comfortable in board rooms, confident enough to think big, or at least differently, driven enough to sweat the details and nagged by enough self-doubt to feel at home among notoriously insecure artists, Humphrey at 50 seems to have found his niche.

"Charlie has a track record of looking at an institution and figuring out different ways to run that railroad. That's what we need," says Janet Sarbaugh, senior director of the arts and culture program at the Heinz Endowments, which has funneled millions of dollars into his proposals over the years.

"If he says something is an important community asset, more people will take notice than might have. He's also an irreverent provocateur and instigator. When you tell him, 'We've always done it this way,' it's like waving a red flag in front of a bull."

Big foot print

"The stuff I do is small potatoes," Humphrey says. "The Glass Center, Filmmakers and the Center for the Arts have a huge programmatic footprint that's really significant in this market. But from a budgetary standpoint, it's miniscule compared to the Carnegie or the Pittsburgh Cultural Trust."

All the more reason to have someone championing their cause, says Carol Brown, former president of the Trust.

"Charlie's not one of the guys who measures success by budget size or their own clout," she said. "He's a very effective advocate for the people and places where art is actually made."

Filmmakers is the prime example. One of the oldest and largest media arts centers in the country, it occupies its modern, sprawling building on Melwood Avenue because Humphrey envisioned it and helped raise the $5 million to fund it. Then he extended the group's reach, working closely with Brown at the Trust to transform a Downtown porn palace into the Harris Theater, and securing some $300,000 to buy and refurbish the Regent Square Theater in Edgewood.

In 2004, when the Center for the Arts at Fifth and Shady avenues was circling the drain, Humphrey was invited to stage an intervention. On loan from Filmmakers, he helped pinpoint the problems, wrote a recovery plan, worked with the board to get funding from the state and private sources to keep the place afloat. Eventually he brought it under the Filmmakers' umbrella, paying off its debt by refinancing the Melwood building. Today, with an annual budget of $4 million, the two venues offer collaborations that neither could have accomplished alone.

"The synergy between Filmmakers and CFA exceeds my wildest expectations programmatically," Humphrey said. "The creative staffs working together have created all sorts of stuff that wasn't there before."

As for the Glass Center, a widely praised LEED-certified facility with a $1 million budget and $500,000 in liability, founders Kathleen Mulcahy and Ron Desmett were concerned enough about its viability to seek Humphrey's help.

"The center was going to need someone with a great rapport with the foundation community, who had run a nonprofit public-access school like Filmmakers and now PCA. No one we saw had those qualities but Charlie," said Mulcahy.

Again on loan, he wrote a second recovery plan, helped raise $25,000 to keep the doors open and another $400,000 to stabilize the operation for 18 months. A long-term solution is still in the works.

Even in his off hours, Humphrey champions the arts, talking up his optimistic vision for the city, writing articles and serving on the boards of Quantum Theatre, the New Hazlett Theater and Squonk Opera.

"He was totally instrumental in our growth," said Karla Boos, founder of Quantum.

Wrestling a pedigree

How big a role his lineage has played in his successes is, he says, an unknown.

"There's no way for me to quantify to what extent my extreme good fortune of birth has enabled me to do what I do," Humphrey says. "I suspect it plays a role, but I try never to capitalize on that. The insecure parts of me say maybe I'd be sweeping floors if not for my background, but I try not to speculate about it too much."

Humphrey's paternal great-grandfather, Arthur Luther Humphrey, was president of Westinghouse Air Brake. His maternal great-grandfather, Charles Donnell Marshall, cofounded McClintick-Marshall Steel, fabricator of parts for the Panama Canal and Empire State Building.

Charles Marshall's youngest daughter, Charlie's grandmother, grew up in the house that is now the Pittsburgh Center for the Arts (his interest in helping the center was civic, not familial, he says, though a few critics questioned his motives). She married Aiken Fisher, the son of Chester G. Fisher, who founded the global research and laboratory instruments maker Fisher Scientific. Aiken Fisher became president of the family firm and was a force in the Allegheny Conference on Community Development during Renaissance I in the 1950s.

"He was my model for civic engagement," Humphrey says.

The young Charlie started out slow, flunking first grade at St. Edmund's Academy in Squirrel Hill and thinking he was dumb for years after that. His parents divorced when he was 8, and his mother took the four children to Coral Gables, Fla., in pursuit of a bohemian life.

She had a serious drinking problem and a number of boyfriends, he says, notably a young Cuban beach club attendant who was in the picture for five years. When the son argued with his mother, which was often, the boyfriend would smack him around as she stood by and watched. (He says he forgave her, "because you just do," long before her death in 1986.)

School was no safe haven, either.

"Charlie was getting the crap beat out of him every day by other kids at George Washington Carver Middle School," in Coral Gables, recalls Rick Humphrey, his older brother by two years. "Our mom was totally out of it. He was just trying to survive. It was brutal."

Their mother eventually married an African-American man who was good to her and the children, but the union turned the family into social outcasts. His stepfather left after four years.

Finally, his grandparents stepped in, and he wound up at the Orme School, an elite prep school in Mayer, Ariz. He was back in the world of privilege, but trailing way behind on every level.

"We were so far over our heads socially, emotionally and academically, but Charlie didn't quit," said Rick Humphrey, who lives in Aspinwall. "It took him two years to catch up. He wound up class president two years in a row.

"Charlie's got great DNA," his brother continued. "He's smart, a hard worker and a good listener. But his upbringing was such that he had to fight for everything and nothing came easy. Both of us grew up ultra-competitive and hungry."

This background may explain the different sides of Charlie Humphrey's persona. There's the guy who wore a ponytail until four years ago (he saw a picture of himself, thought "What a moron," and cut if off); who dresses down, makes self-deprecating jokes and furnishes his office at Filmmakers with Gulf Oil castoffs whose leather seats look like they've been hacked by a madman with a meat cleaver.

There's also the guy who lives in a large, gracious home in Point Breeze, has a country house, likes nice cars and guitars, and whose daughters were debutantes at the Cinderella Ball.

Then there's the paradox of his rock band, The Shanks, which has two CDs and a following from occasional gigs around town. He writes most of the songs, plays guitar and sings lead. He also hates his own voice and suspects his bandmates are humoring him.

"The other members of the band are all great musicians," he says. "Why are they playing with me?"

"That," says brother and bandmate Rick, "is a typically conflicted remark. He's so insecure. ... If he believes it, why is he standing in front of hundreds of people?"

Because, Humphrey replies, "I want to overcome my fears, and I want to get better."

Circle of influence

Not everyone loves Humphrey for his efforts. As an outsider coming into a crisis, he has fired people, stepped on some toes and alienated some board members. He's also had a very public dispute with Dawn Keezer, director of the Pittsburgh Film Office, over supporting local filmmakers. But at local foundations, which he calls "unusually generous and enlightened," he gets a lot of praise.

It doesn't hurt that he's a donor-adviser to the Fisher Fund, created by his great-grandfather, which gives away $600,000 to $1 million a year for science education and, at times, the arts. But that money, he stresses, is not his own.

"In no way am I a philanthropist," he said. "That's out of my league. I'm three generations removed from the wealth created in my family."

Instead, he says, "I'm just a regular person who gives money to causes I care about."

From the Orme School, Humphrey went to Whitman College in Walla Walla, Wash., because, he said, "It was as far away from Miami as I could get."

There he studied philosophy, ran track, worked at a community radio station and met his future wife, Nina Gram. They moved to Humphrey's hometown for her to attend the University of Pittsburgh Law School. (The couple had two daughters, now in their 20s. They separated in 1994, and six years ago he married Laura Jordan, former director of finance at Filmmakers, who also has two daughters.)

Humphrey got a job at WQED-FM, where he did producing and fundraising for four years. After a stab at advertising, he got an offer from John Burstein, founder of In Pittsburgh News Weekly, who hired him as editor and then publisher. He was 28. "It was a blast," Humphrey says.

The paper thrived during Humphrey's six-year tenure. Then, in the Good Friday edition of 1992, he ran a Gary Huck cartoon of Jesus on the cross with the letters "TGIF." Some readers took offense, and Burstein wanted him to print an apology. Humphrey quit instead.

"Bail-Bondsman bravery," he calls it now. "I knew I wasn't going to starve."

The two haven't communicated since. Burstein, now living in Boston, still speaks highly of his ex-employee, but it's clear he's still smarting over being left in the lurch by someone he trusted.

"Walking out that way put me in a really tough spot," Burstein said. Humphrey keeps the cartoon in his office as a reminder of that part of his life -- not, he says, for any moral lesson. "I was wrong and I was right," he says, "as I continue to be about many things."

When he heard about the job opening at Filmmakers, Humphrey was one of many to apply (as a child he hoped to become a filmmaker himself). He wasn't the search committee's first choice -- too corporate, they said, based on the suits he wore to the interviews. But after four meetings, they hired him. Sixteen years later, it's still the center of his circle of influence.

How effective he can be in his latest mission remains an open question. "The Glass Center is a patient on drugs," he cautions. "When the drugs wear off there better have been serious therapy or it's gonna be a world of hurt."

These days he splits his time among the three locations. There is a risk that he's spreading himself too thin and that Filmmakers may suffer for it, but he sees it otherwise, saying, "I work with great staffs who probably do more and better work when I'm not hovering around."

Yet there will always be some free-floating doubts that are part and parcel of his personality. Asked if he's stopped worrying about the PCA's finances, he shakes his head. "That would be hubris. I never think I'm out of the woods."