Gail Smith, a lawyer, needed a few thousand dollars to help incarcerated mothers keep custody of their children, but she didn’t know where to look.

For one thing, it was not a popular cause. This was in 1985–at the height of Ronald Reagan’s popularity–when most people seemed more bent on cracking the heads of lawbreakers than assisting them. On top of that, the mainstream foundations in town were being deluged with requests from other not-for-profit groups advancing more conventional causes.

Smith finally found a sympathetic audience in the board of the Crossroads Fund; they listened and then delivered to the tune of $4,000.

“I can’t say enough about Crossroads–they were our first donor,” Smith recalls. “And that’s really important. There are a lot of foundations who won’t give you money if you don’t already have money to begin with. It’s strange, but you have to not need their money before they give it to you. They want a guarantee that your group is stable. Crossroads is much more open-minded to groups just getting started.” Within a matter of months after the Crossroads grant, Smith had raised about $80,000 for her organization, Chicago Legal Aid for Incarcerated Mothers.

Commendations like Smith’s make the struggle at Crossroads a little more bearable. They are a relatively small foundation dedicated to a big cause–nothing less, in fact, than “a more equitable distribution of power and wealth in this country,” according to Sarah Bradley, who cochairs the group.

Along the way they have seeded a wide variety of organizations devoted to causes so obscure, radical, or controversial that they’re usually overlooked by the larger foundations. “The kind of groups we fund are not likely to get money from the mainstream foundations, like the Chicago Community Trust,” says Bradley. “At least, not at first.”

“Crossroads has always been in the vanguard of foundations,” adds John Hetman, coordinator of member services for the Donors Forum, an association of 150 Chicago-area philanthropic foundations. “They fill a vital need in seeding and serving new groups. They fund the small grassroots organizations that struggle with critical social issues that other foundations are hesitant to address.”

Last year, for instance, Crossroads gave money to 40 organizations, whose causes ranged from opposing Nicaragua’s Contras to promoting Afro-American art. At times, the group’s funding seems at cross purposes. For example, Crossroads has offered something of a lifeline to local groups advancing equal rights for gays. Yet last year it also awarded $2,500 to Venceremos, a group that advocates better relations with the Castro government in Cuba–which has a long-standing record of jailing and mistreating homosexuals.

“The fact that we fund Venceremos doesn’t mean we tolerate or endorse everything Cuba’s government is doing,” says Norman J. Groetzinger, a former Crossroads board chairman. “The problem is that almost all information about Cuba is controlled by the U.S. government. And we feel that Chicagoans should be exposed to other avenues of information about Cuba.”

The largest Crossroads grant last year was $5,000. It was awarded to the LeClaire Courts Resident Management Corporation, a group of tenants who manage their own south-side housing project. A typical grant is about $2,000.

“We don’t pretend that our money will cover a full-time salary or yearly rent,” says Judy Hatcher, the associate director of Crossroads. “But the extra one or two thousand at the margin is very critical. It helps pay all sorts of office expenses, and it has a strong morale-boosting factor. It says, somebody out there thinks your work is important.”

Crossroads, formed in 1980, was the brainchild of Robert Johnson, then director at the Wieboldt Foundation. “Bob had read about the Funding Exchange, which is a national coalition of groups very similar to ours, and he decided Chicago needed one,” says Bradley. “We wanted a board of activists, people who were not much different than the organizers of the groups we were funding.”

The notion at the time was to raise funds from the sons and daughters of progressive, wealthy families. And they have received contributions from such donors as Robert Weissbourd, whose father, Bernard, is a successful developer of downtown real estate.

Over the years, however, under the direction of executive director Jacqueline Schad, Crossroads has broadened its fundraising base. It appeals for donations as small as $25 and raises money at special parties where donors pay a nominal sum to mingle, over drinks, with celebrities like Neil Tesser, jazz critic and WBEZ disc jockey.

Hetman explains Crossroads’ unusual position in Chicago’s donor community: “There are not many foundations in Chicago that raise their money the way that Crossroads does. You have some family foundations, which are basically supported by family-run businesses. There are large organizations, like the John D. and Catherine T. MacArthur Foundation. Their assets are $2.3 billion, and they gave away $121 million last year. Some foundations are established by a posthumous endowment. The board members then invest the endowment and give away the interest.”

“Our job is tough because we have no endowment,” says Bradley. “We start all over every year. We raised about $200,000 last year and awarded about $120,000 in grants. The rest of the money went for staff, office expenses, and general overhead.

“Some of our donors come out of families with long histories of philanthropic involvement. You have other people who didn’t realize that they were wealthy until they became adults and they inherited money. They get embarrassed–having wealth wasn’t their self-identity–and they want to invest it ethically.

“Other than that, we have to do a lot of fund-raising. We worked very hard to democratize our funding base. We started with a small group of people, and now we have dozens of donors. You can give us $1,000 or $5; we have no minimum. We have coffees. We invite people to events. It’s unpredictable. You can ask people for money for five years and not get anything. Then suddenly you get a big check.”

Over the years, their mission has broadened as well.

“We’ve gone through an evolutionary experience,” says Groetzinger. “We all had a strong notion for bringing about social change through democratically controlled, geographically based organizations. But then you see that a lot of the new residents of Chicago come from Central America, where their lives were disrupted by U.S. involvement. So we give to groups that are moving to change foreign policy.

“It’s an incredible educational experience. With the gay-lesbian community, you’re dealing with a predominantly white, middle-class community. So it’s not a class issue, and some of us wondered if that’s where we should be spending our money. We struggled with that one for a long time, and everybody came to understand that issues of oppression are the same everywhere.

“I don’t think that any of us would have predicted we would fund an arts group. But we came to understand the importance of films in the whole movement toward social change. So we fund arts projects so long as they are linked to organizing. We’re not interested in a movie made by a dispassionate observer for profit.”

Crossroad’s also has funded organization’s involved in labor struggles, even though that was not initially a priority.

“Almost all of us came out of one of four movements: civil rights, antiwar, women, and the gay and lesbian movements,” says Groetzinger. “As a result, many of us had a strong bias against labor. We saw it as a reactionary force in foreign relations or civil rights. But you have to overlook your prejudices and see that the rank and file are different than the people on the top.”

After layoffs at Stewart-Warner, a Lakeview-area auto-parts factory, left thousands of Chicagoans without jobs, Crossroads made a decision to fund the Coalition to Keep Stewart-Warner Open.

“We formed two-and-a-half years ago to put pressure on the company to maintain its work force here,” says Michelle Couturier, staff person for the Stewart-Warner coalition. “The company once had a work force of about 7,000 here. Now it’s down to 1,500, as Stewart-Warner moved much of its operations to a division in Tennessee.”

Most of the Stewart-Warner group’s $43,000 budget comes from church groups: the Campaign for Human Development, a foundation wing of the Chicago archdiocese, and the Committee on the Self-Development of the People, sponsored by the Presbyterian church. Last year, the group received $3,000 from Crossroads.

“We were turned down by a whole lot of groups before Crossroads gave us money,” says Couturier. “Their initial reaction was that we’re a bunch of kooky union activists and neighborhood people who are losers. We were told by a whole group of foundations that we were too risky to get involved with. A lot of them get their money from corporations, and they didn’t want to give money to groups that beat up on corporations. Or they sent us nice letters saying we’re too politically charged, or our focus is too narrow. That means we are focused on Stewart-Warner and not the overall industrial decline in America. It’s kind of frustrating when you’re working on a local problem and then you’re asked to focus on national issues.”

Crossroads has also helped groups through the awkward early stages of organization, among them, of course, Chicago Legal Aid for Incarcerated Mothers.

“They’re great for giving advice, and I can always use it,” says Gail Smith. “This is basically a one-woman operation: me. I type my own grant applications and handle almost all of the cases. Last year I saw about 160 individual clients, and I taught about 285 in my classes at the correctional institutions.

“We’re pushing for more alternatives to incarceration. There are an awful lot of women who are in jail for minor economic crimes. Their children are often sent to foster homes, which doesn’t make any [economic] sense. The state pays about $17,000 to lock up a woman, and for one child in foster care it costs about $4,000.

“I do a lot of legal guardianship, so children can be taken care of by a family member while the mother is in jail. I fight for more visitation rights; but I’d like to see more alternative sentencing. That doesn’t mean letting someone off the hook but giving them an appropriate sentence. I had this one client who got two years for a forgery case in which she stole about $1,500. That’s ridiculous. [When she got out] she had to fight her mother-in-law to get her three-year-old son back, but she won. She’s in drug-counseling classes now and working as a receptionist, and the boy is so happy. Well, I told this story to a group of women in prison, and you should have seen their faces light up. They want to believe that they can make their lives better.”

Smith hopes to receive more money from Crossroads, once the foundation reviews proposals being considered for next year’s grant-giving cycle.

“Sometimes it can get very frustrating,” says Bradley. “We know the needs out there are great, and yet our budget is only a couple of hundred thousand dollars. But I suppose you have to take a long-term view. We came into existence at the outset of the Reagan era–a very tough time for progressive organizations. And yet a lot of us have survived. We’re all hoping for better days as we move into a new era.”

Art accompanying story in printed newspaper (not available in this archive): photo/Bruce Powell.