If Philadelphia can claim a steady parade of philanthropic captains in the last two centuries - from Benjamin Franklin to Walter and Leonore Annenberg - it is also true that the continued supply of such leadership lately has been somewhat in doubt. In terms of really big givers, after Gerry and Marguerite Lenfest - who have donated more than $1 billion of their fortune in the last decade and a half and promise to disburse the rest - who will come next?

John S. and Leigh Middleton have the means to be next, and in fact have been quiet philanthropists for some time. Now - reluctantly - they may be ready to step up their visibility and fully embrace the mantle. Late Wednesday afternoon at the Philadelphia Museum of Art, they will accept the Philadelphia Award, the venerable medal whose previous honorees include Edmund N. Bacon, Richardson K. Dilworth, Leopold Stokowski - and the Annenbergs and Lenfests.

For the Middletons, accepting the award signals a problematic shift in how they think about their place in civic life. They would much prefer to operate anonymously.

"We did not want to have to be outed. It's very uncomfortable for us," Leigh Middleton, 55, said during an interview last week. "We're spotlight avoiders," said John, 59, on whom the spotlight has shone nonetheless in his role as a Phillies co-owner.

Still, the Middletons understand that philanthropy is to some extent about leverage, a realization that has played out over their eight-year involvement with Project HOME, which provides services to homeless Philadelphians.

"Several people have said to us over the years that you can't maximize the good you do if you stay in the shadows the whole time and remain anonymous," John said. "We found, particularly with Project HOME, three or four of us will go meet with people, and [executive director] Sister Mary Scullion will say, 'The Middletons are giving X, we want you to give Y,' and you can see it makes a difference to someone you're trying to solicit money from that you are in there and saying we want you to give, and not staying on the sidelines.

"Ultimately, at some point, when you have the capacity that we have, you have to rethink what you are doing and the way you are doing it. There is a responsibility that comes with that."

Already, the Middletons have made some impressive gifts: tens of millions to Project HOME and the University of Pennsylvania; $16.2 million to the Philadelphia School District and other educational institutions; and major support, along with the Lenfests, to expand Teach for America.

"To come into contact with them you would not suspect they are who they are," said Susan Sherman, Independence Foundation president and a Project HOME trustee. "They are just lovely, modest people who are doing the right thing."

Scullion, in fact, had no idea who they were when a banker friend called her and asked if the couple could tour Project HOME. "I wasn't sure what the agenda was, but a couple of days later I got a check for $100,000. That usually doesn't happen after a tour," she said. Soon after, another check arrived. "So I picked up the phone and asked whether they wanted to get more involved." Leigh Middleton joined the board.

Having enough money to give it away in serious chunks came relatively recently for the couple. In 2007, Middleton sold privately held cigar maker John Middleton Inc. - started by his family as a Philadelphia tobacco shop in 1856 and at the time the world's third-largest cigar maker - for $2.9 billion to Altria Group, parent of Philip Morris USA. He was 52.

"I sold the business, and I wasn't sure what I should do with my life," he said. "But Leigh was pretty darned sure what I should do with my life, and essentially told me, 'Look, you won't need to work anymore, you have all the money you will ever need, and if you continue to work it will only be out of ego. You need to take your experience and turn to helping other organizations, nonprofits, and use the money you made to help them do it.'"

So he did. Leigh, who had done some social-service work as a junior at the Shipley School, was already on Project HOME's board, and the couple poured their energies into the organization. "I had read Lisa Richette's The Throwaway Children [the late judge's 1969 book on the juvenile justice system in Philadelphia], and I was struck by how unfair life can be," Leigh said.

Of all the city's needs, why homelessness? Several qualities that appealed to the Middletons came together in Project HOME. "I would say that what we're most drawn to is trying to help people who can't help themselves - they may have mental illness, drug addiction, vulnerable people in society," Leigh said. "It has always seemed to us that it is easier to raise money for things like cultural institutions than these kinds of groups. It's not very glitzy."

John was impressed with Project HOME's focus on metrics - its tight handle on finances, success rates, and goals. "I guess that's just my business training," he said. "I don't think you can be CEO of a company as long as I was CEO, and grow it from what it was to what it was when we sold it, without approaching your daily life that way.

"Strategically, you have to have a vision, you have to take that vision and translate it into a strategy, and take the strategy and translate it into tactics, and create goals for those tactics, create milestones for those tactics, and constantly monitor your progress against the long-term goals, and make sure you're on track and be able to identify when you are off track, and make adjustments and move forward. There is a discipline to doing that."

But he was wary of grafting his business-think onto his nonprofit ventures. Then he met Jim Yong Kim, a cofounder of Partners in Health who is now president of the World Bank. Kim was president of Dartmouth College when he started to ask Middleton some pointed questions about Project HOME's ultimate ambitions.

"The interesting thing for us is that we had been working with Project HOME for three years, and it was like a lightbulb went off. What Jim talked about, how you should be running these charitable organizations, was precisely how Project HOME was running. It was Jim who encouraged us to dream bigger and stop trying to nibble at the problem."

What could be bigger?

One day, at a Project HOME meeting, Middleton stopped a conversation with cofounders Scullion and Joan Dawson McConnon. "They were talking about some project they were thinking about, and I said, 'Let me ask you a question. What do you have to do to end homelessness? What does the solution look like?' And they looked at me and said, 'You know, John, we've never had the luxury of thinking about that question because we've always been living hand-to-mouth.'

"I said, 'Well, go away and think about it,' and after six months and a lot of interaction, they came up with a strategic plan. I said, 'OK, let's go do it.' "

The Middletons were fully supportive of the $300 million plan to end chronic homelessness, and to them, "do it" meant making a gift of $30 million. "It took my breath away," Scullion said of the moment she learned the size of the gift, the largest in Project HOME's history. "It was almost like, did I hear that correctly?"

In a recent speech honoring the Middletons, Kim put their philosophy this way: "John and Leigh understand that it's not enough just to feel compassion. It's not enough to want to do the right thing. You've got to actually know if you're making a difference, and if you're not, you've got to rethink, look for other inspirations, find better ways of doing it, and keep going at it, because the point is not your generosity. The point is what you actually accomplish on the ground."

When Arthur Rubenstein was dean of the University of Pennsylvania's medical school, he approached the Middletons for a gift and was rebuffed. Penn's medical school was consistently ranked at the top of the field, and "it was hard for me to understand how I was benefiting a broader goal. I declined," Middleton said.

Penn returned with another idea, involving homelessness. "I said, 'You're kind of getting there, but it's a little narrow for me.' Then Arthur said to me at one point that if you really want to be in the elite of medical schools, there are five areas you have to be great in, and one is neuroscience, and he said Penn is good but has the ability to get a lot better, so we decided to go after that and give them money that allowed them to recruit some of the top people around the world and get them started."

Middleton, though, sees the heretofore-anonymous gift of $16.3 million to Penn Medicine's Neuroscience of Behavior Initiative as an investment. "The expectation is you're going to go out and find grants to sustain this over time. We're venture capital."

The Middletons, who grew up in the Philadelphia suburbs and live on the Main Line, have two grown children and spend some time skiing and golfing. John is busy at alma mater Amherst College as chairman of the board's building and grounds committee. They go to a lot of Phillies games. Like the Lenfests, they dabble in art.

"We collect a little bit. We tend to look more than we buy," John said. Here, again, modesty may be at work; ArtNews last summer included them in the Top 200 list of the world's most active collectors.

The family business now, they say, is philanthropy. And again, inspiration comes from the Lenfests, who in turn cite Walter and Leonore Annenberg as their inspiration - suggesting, perhaps, the continuity of a certain philanthropic lineage.

"One of the things Gerry has done very well and we've tried to emulate is provide up-front seed money," John said. "There are problems Gerry could have solved himself - you need a check, I'll write you a check. Instead, Gerry's tendency is to give part of X, but then use that to get other people.

"The purpose is to raise people's consciousness of that issue. It's really trying to make the Philadelphia region aware of these issues and get people involved with them. Because eventually we're all going to die, and when we die, if the work we've done falls apart, then you haven't left an enduring impact on the world. And that's what we would like to be able to do."



Amount that cigar maker John Middleton Co. sold for in 2007.


Amount the Middletons are giving to Project HOME.


Donation to the Philadelphia School District and other educational institutions for training in workforce and professional development.


Donation to Penn Medicine's Neuroscience of Behavior Initiative.EndText