The following is a conversation between Dr.Helene Gayle, the President and CEO of the Chicago Community Trust and Denver Frederick, Host of The Business of Giving on AM 970 The Answer in New York City.


Dr. Helene Gayle, President and CEO of the Chicago Community Trust

Denver: A person’s career path often starts with working with a local organization, then tackling bigger issues on a national stage, and ultimately, being an integral part of an international enterprise.  But that isn’t always the case. For instance, my next guest has had leadership roles at the Centers for Disease Control, a US federal agency, the Gates Foundation, leading their HIV/AIDS programs, and the international human services organization, CARE. But now, she is turning her attention to helping improve the lives of people in one of America’s greatest cities. She is Dr.Helene Gayle, the President and CEO of The Chicago Community Trust.

Good evening, Dr. Gayle, and welcome to The Business of Giving! 

Helene: Thank you. Good to be here. 

Denver: Before I get into the Chicago part of your organization, let me ask you about the Community Trust piece, because I know there are some folks out there who are a bit unclear about what they are, where their money comes from, and how they work. So, fill us in. 

Helene: Great. Well, The Chicago Community Trust, as many people think because of the name “The Trust” first, they are confused — is it a bank? But when I say a “community foundation,” it still is something that a lot of people aren’t familiar with. 

And so, a community foundation is this wonderful creation that came about just over a hundred years ago, and our foundation was one of the earliest ones.  That was an opportunity for citizens that were concerned about their communities to pool their resources in an organization that could then distribute those resources to the greatest needs within the community. 

So, we have both an arm that focuses on donors and people who want to be generous to their communities, and then also an arm that focuses on where can those resources be used to create the greatest change and meet the greatest needs within a given community. So, it’s a wonderful opportunity for citizens to aggregate their resources, if you will, to make a difference in their own communities.

Denver: Would it be anything analogous to the concept of the United Way, where you collect money, and then the people at the Trust have an idea of what the needs are in the community and try to leverage that in the most intelligent way, to do the most good? Or would be something different than that? 

Helene: It’s very similar to the United Way. Obviously, United Way has primarily focused on workplace giving, and within the United Way system, people generally designate for a specific organization that they want to fund.  In a community foundation, people can give their resources in an unrestricted way so that we put it to use; or they can, through donor-advised funds, actually designate where they want their resources to go. 

So, we have a fair amount of latitude to invest in the ways that we think can make the biggest difference within communities, but we also are able to give resources to organizations that donors designate directly. So, there’s a bit of the same sort of direct designations as United Way has, but it’s all the same sort of idea: How do you aggregate resources that can then go to serve the greatest needs within a community?

Denver: Yes. Have impact

Helene: Exactly 

Denver: How many nonprofit grants do you give out?

Helene: The number of grants, I’d have to think about. So, we have about $3 billion in assets under management. We give out around $400 million every year, and we take in roughly about $350 million to $400 million every year.

Denver: In addition to grants, do you get involved in loans or impact investing or any things along those lines?

Helene: Well, we do now. We’ve started giving out loans and other ways besides just grants so that people can, in fact, invest in building small businesses or other things that loan or equity could be more useful for. So we’ve really gotten started in this whole area of impact investing, and I think it gives us a broader range of ways besides just grant funding to actually have long lasting, sustained impact within communities.

The millennial donors are different. They want to be more involved. They’re more directly involved with where they contribute their resources, and directly involved in a sense that they want to actually be thought partners; they don’t want to just give. 

Denver: When I think of a community foundation, I sometimes think of older donors because it’s a bit more of a traditional vehicle. How are you doing with the millennials? 

Helene: We’re looking at that issue and, clearly, the millennial donors are different. They want to be more involved. They’re more directly involved with where they contribute their resources, and directly involved in a sense that they want to actually be thought partners; they don’t want to just give. They also are very interested in this area of impact investing, and how do you make loans, how do you help start businesses, how do you think about things, in not the traditional nonprofit way. 

And so, we’re looking at these different kinds of approaches that will appeal to the next generation of donors because, as you said, I think, oftentimes, we find that the more traditional donor is no longer the donor of tomorrow. 

…until you look at untangling some of these issues – the issues of violence, poor health, lack of access to educational opportunities – they won’t be solved until you solve these root causes of this widening wealth gap that exists in Chicago.

Denver: I’m going to ask you, if you would, Helene, to paint a picture of the city of Chicago because we have a lot of listeners who aren’t familiar with Chicago. I think you’ve got some sports fans who know maybe the Cubs play on the north side and the White Sox on the south side, but Chicago is truly a tale of two cities. So, if you could just sort of give us a visual map of the city. 

Helene: I didn’t know Chicago very well before I moved there, and it’s been wonderful to discover some of the incredible contributions I’d forgotten: The Cracker Jacks were created in Chicago; We all know Sears and Roebuck; and so many things that Chicago brought us. But I think that in recent years, Chicago has been known more for things like the issue of violence and other things. And so, I think there is, as you said, a real tale of two cities.

On one hand, Chicago has one of the most incredibly dynamic downtowns ever. It’s beautiful, with the Lakefront and Millennium Park, and it has some of the wealthiest businesses in the world. On the other hand, you can go five-, six miles away from downtown and see very clear undervalued, disinvested communities, and that’s where a lot of the things that we hear so much about… some of the violence and other issues… that’s where that takes hold. 

Denver: Would that be more in the south part of the city?

Helene: Well, south and west sides of the city, primarily where communities of color, black and Latinx communities have ended up, based on a lot of long-standing issues related to residential segregation and some of the policies… federal policy and other that then ended up being enacted at the local level… that led to this extreme segregation and very persistent patterns that have really left communities out of the economic opportunity. 

And so it’s one of the issues that we’re trying to address at The Chicago Community Trust because until you look at untangling some of these issues – the issues of violence, poor health, lack of access to educational opportunities – they won’t be solved until you solve these root causes of this widening wealth gap that exists in Chicago.

Denver: And to underscore that 5- or 10-mile trip, from one of the more opulent areas to one of the more low-income areas… in Streeterville, which is one of the nicer areas, residents live up to age 90–

Helene: Yes, higher than the US average.

Denver: And in Englewood, which is in one of those areas that you were just speaking about, it’s age 60.  That is the largest divide in the United States. Now, I know that just can’t be because people who are living in Englewood don’t have access to health care; I’m sure it’s a part of it. But speak a little bit more as to the whole breadth of issues that create that horrific disparity.

Helene: It’s jaw-dropping when you think about this, and having spent so much of my life working in developing countries around the world, it’s been painful and shameful for me to come back to the United States and see these kinds of glaring inequities that manifest themselves in things like the health disparities. But, as you mentioned, this is more than just a lack of access to health services. 

In Chicago, there are several institutions. There’s one particularly on the west side that Rush University Medical System has spearheaded called West Side United that looks at what we call the social determinants of health. They looked at this glaring inequity in health and recognized that if you didn’t look at issues like jobs and employment, access to safe nutrition, public safety… so that people were able to walk and exercise, access to education, all of these root causes, if you will, that undergird these health disparities, improving health access alone was not going to do it. 

And so more and more, this issue of what we call social determinants of health – economics, education, safety, food, et cetera – are the things that people are focusing on more if they want to have an impact on these health disparities. Again, the health disparity is just kind of the tip of the iceberg. It’s more of a symptom than actually a cause. 

I think there’s a variety of different ways in which one can approach it, but I think at the core of it is the fact that these things didn’t happen because of individual behaviors alone. They happen because of policies that really systematically robbed people of the opportunity to be part of the economic engine of this nation.

Denver: Yes, and along those same lines, disparity in income. The wealth of white families is 10 times greater than African-Americans, eight times greater than Latinx. How do you think about a problem of that dimension at The Chicago Community Trust and get your arms around it, get the right mindset in terms of trying to tackle it, develop a strategy to take on something that large?

Helene: We’ve actually put as our highest organizational priority working to help close the racial wealth gap because we do believe that unless we tackle that issue, all these other factors, which are symptomatic of this racial wealth gap, are not going to be solved. So it’s so core, it’s so fundamental, and so we said this is going to be our highest priority. 

I think there’s a variety of different ways in which one can approach it, but I think at the core  is the fact that these things didn’t happen because of individual behaviors alone. They happen because of policies that really systematically robbed people of the opportunity to be part of the economic engine of this nation. And if you look at a recent report that came out that showed that through the practice of redlining and contract house buying, which were all federally-sanctioned policies, that $3 billion to $4 billion of wealth was robbed from the black community in Chicago; and it’s well documented. And so, these are public policies, and so I think a big piece of it has to be looking at: what are the kinds of public policies that can actually start to redress some of these issues? 

In addition to this, you look at a lot of the communities on the south and the west side in Chicago, and there has been widespread disinvestment in these communities. So, there has to be a plan to think about how do we start reinvesting in those communities. How do we give capital access to people who have the entrepreneurial spirit and the ability to start small businesses, but don’t have access to capital? So, we’re focusing on issues like that. 

We’re also focusing on the issue of debt because on one hand, you can create wealth, but if it gets taken away by discriminatory practices of fines and fees and other things… predatory lenders that just kind of keep people in this downward spiral of debt… you’re not going to be able to solve that. 

Dr. Helene Gayle and Denver Frederick inside the studio

Denver: That’s a great point, to tell you the truth. People overlook debt often when they’re thinking about this, but that can just paralyze you for the rest of your life.

Helene: Well, huge! And when you think about school debt, so many young people from backgrounds where they don’t have the ability to access the kinds of loans, or end up in schools where they get such a loan debt burden, don’t ever finish because they can’t economically, but then they carry this huge debt burden. 

So, we’re looking at all these issues around access, ways in which people can accumulate assets, whether that’s through entrepreneurship, whether that’s through better opportunities for jobs, but also looking at the debt side. And overall thinking about: what are both the policies as well as the programs that can make a difference? 

Denver: A great tool in this endeavor, too, which again I don’t think people fully understand… so I hate to ask you to teach us all here this evening, but I will… it’s the Earned Income Tax Credit. Speak a little bit about that and how it works.

Helene: So without getting too technical, Earned Income Tax Credit is something that we already have. It’s a policy that exists that allows low- and working-class families to get a tax credit, if you will, if they fall below a certain income level. This is something that could be expanded. It’s a way of giving working families, and oftentimes—I’ve talked to many of the people who get earned income tax credits—these are people who have done everything right.  They’ve gotten education. They’re working two and three jobs, but they still can’t make ends meet.

So, the Earned Income Tax Credit is something that gives a little bit of relief, gives a little bit of a cushion, if you will, to people who are already struggling to make ends meet. But as so many of these programs, it’s cumbersome. It’s complicated. People who are eligible for it don’t even know that they’re eligible. It comes as a lump sum at the end of the year. How many of us can manage on a lump sum once a year?

Denver: Give it to me every two weeks. That’s the way we operate our lives.

Helene: Exactly. If the periodicity of it was straightened out, if there was a way of helping with the applications that are very cumbersome, if there was a way of doing outreach to people who are eligible. And also another kind of wonky piece of this is that people have to constantly be figuring out: “If I get this, if I take this Earned Income Tax Credit, and I do make a little bit more money, do I then get kicked off of that just at the time where I’m starting to make a foothold?” 

So, we also have to start thinking about: Are we penalizing people for the very thing we want them to do, which is to get more economically viable, but then we pull the rug out from underneath them? So there’s a lot of these things that could improve the Earned Income Tax Credit system, that could give real relief to people who are just starting to get an economic foothold.

…at the end of the day, any problem can be solved if you have the right plan, political will, and resources, and if you have a community that comes together and looks at the whole picture

Denver: Let’s talk a little bit more about gun violence; you brought that up a moment or two ago. And for so many of us around the country, when we think of Chicago, we think of the news reports that come to us after a long weekend on how many people were shot. It’s just so tragic to hear all that. The income inequity you talk about exists in other cities, too, and all these other root causes, but it seems that there’s just this level of violence in Chicago, which is significantly greater than many of the other major cities around the country. Why do you think that’s occurring?

Helene: First, I always have to start by telling people: Chicago is really, overall, a very safe city. And so many friends, when they ask me “Do you feel safe to walk down the streets at night?” By and large, Chicago is a very safe city, and we know that violence is concentrated in certain neighborhoods. That doesn’t make it any better by any means, but I think it does highlight again this notion of the tale of two cities; and where we see violence, we also see concentrated poverty. 

I think it’s difficult to tangle out why Chicago, more than others. But I do think that when we look at some of the cities that have really made a difference, at the end of the day, any problem can be solved if you have the right plan, political will, and resources; and if you have a community that comes together and looks at the whole picture, which is partly public safety. We know that police have a role, but are we building a police force that’s working with a community, or is it working against the community? How do communities feel like they are being protected? 

We know that in Chicago, there’s a huge rate of unsolved homicides. If people are able to feel like there is no recourse for communities where they recognize that the violence is a huge problem; they want those homicides solved. Somebody wants to know who killed their son or daughter. So, there’s clearly a policing part of it, but there’s a huge part that has to do with: How are you putting together a more comprehensive plan that looks at policing, but also looks at economic development, also looks at education? 

This is not a short-term fix, and without a long-term plan that looks at: How do you interrupt violence in an immediate sense,  but also: How are you fixing the sustained problems that led to this, we’re not going to be able to get anywhere. But we know that there are cities that have made a dent. So, again, it’s back to political will, resources, and a plan.

Denver: Yes. And at the heart, Chicago has all those things; They really do. It’s an incredible city. I know they do not have an Office of Violence Prevention the way we did in New York and the way LA did, so there’s some things I think they’re going to be able to pick up and try to address. And I know you’re part of this Chicago Fund for Safe and Peaceful Communities, which was a pilot a few years ago, and it’s going to be going again this summer, right?

Helene: Right. And so we have put out resources through the summer fund that allows communities to come up with their own solutions for the summer around how they can deal with what we all know is a resurgence of violence during the summer months when young people are out in the streets, and it’s warm. So, we know that the summer months, there’s always an uptick in violence, and so these resources give communities the ability to come up with some of their own solutions that they think will make a difference. 

But again, I think as you point out, there are things that Chicago could learn from some of the cities like New York and LA and others, where they have had a sustained focus on this, that could make a big difference. I know you have one of your other guests who will be speaking, Arne Duncan, has really done so much in this arena and really starting to pilot how working with populations who are at high risk for violence, what are some of the ways he can make a difference?

Denver: When we think of The Chicago Community Trust, we think of people who give you money, and we think of grants going out, but I know you look at that organization as being so much more of what you can mean to the community and how you can impact it, beyond the money part, the money piece of it. Talk a little bit about some of the things you’re thinking of doing to make an impact in Chicago. 

Helene: I think when I look at an institution, it is both the things that it does in a tangible way. As you said, we receive donations and we also make grants to the communities, but we’re also an institution that is respected. We’ve been around for almost 105 years now. It’s seen as an organization that has always been a fair and honest broker for the community. 

So, I think in some ways, we have the ability to influence beyond just our dollars. We’re really thinking about: How do we use our voice as an institution? How do we help to convene others who are thinking about the same issues that we can? Because I think it’s by really developing those kinds of partnerships that we can have the biggest impact. 

So, we see our ability to be an influencer, to be a convener, to be a thought partner on some of these important issues for the community. And I think, we hope to build some of those aspects even more than we have in the past.

Denver: That’s great. You also look to engage the voices of the community, and often voices that don’t get heard quite often, and one of your tools for doing that is something called On the Table. Tell us about it.

Helene: I think it’s a great program, and I can say that because it started before I got there. But it’s a chance—taking this concept that sometimes, breaking bread together and having difficult conversations is the way that you can bring people together around issues. 

And so, we started about five years ago, six years ago now, these On the Table conversations. Every year in May, throughout Chicago, there are thousands of table conversations, dinner conversations going on where somebody voluntarily is a host, invites people around the table to talk about the issues that matter the most to them as citizens of Chicago. It’s a great chance for people to have a conversation and to share with people who they may not have talked to as much in the past.

This year, we did something a little bit different because in the past, it’s kind of been: Have a conversation about whatever you want to talk about. And this year, we said because we have this opportunity of a new mayor… and kind of historic mayor in many ways, one who is very focused on the issues of equity throughout the community… let’s have these conversations as a memo to the mayor. And so, people throughout the city use that as an opportunity to share with our new mayor : what were the things that were top of mind, and what did they want to see from her in her leadership? 

And so, it was a really galvanizing experience for the whole community to come out and share in this day of talking about lifting their voices, to actually say what they want to see out of our mayor for the next few years.

Denver: Let’s talk about your new mayor, Mayor Lori Lightfoot. It is an exciting time in Chicago. Tell us a little bit about her, and what you’re hoping to see from her administration.

Helene: Lori Lightfoot is somebody who came with incredible credentials, having been a lawyer for decades, an African-American, gay woman, who had never served in elected office before, although she had worked very closely in several different government posts. 

She came as kind of a fresh voice in a way, and I think really came in with a real commitment to these issues of equity, and really wanting to focus on some of the things she had been very involved in – police reform. These issues are very close to her and her administration, and she’s prioritized, she’s developed as an example the first ever Office of Equity within her administration. So, I know she’s going to focus a lot on these issues. She’s put a big focus on economic development in communities on the South and the West Side, and particularly the West Side, which has been particularly forgotten in a lot of these discussions. 

So I have high hopes for what she can do, or what she hopes to do. I think if you don’t have the vision, you’re not going to get there. She comes in with, I think, a very exciting vision. On the other hand, we all know Chicago politics are tough blood sport, but she’s come in and I think, in a way, that has been courageous. She shows that she’s willing to take on tough battles. And so, I’m incredibly energized, and I think a lot of people are incredibly energized by her vision, by her energy, by her courage, by her boldness. She’s known to be sharp; she’s known to be tough, and that’s what I think it’s going to take.

Denver: Well, interesting times, and you know you throw on top of that, you have a new governor out there as well, correct?

Helene: We do. We have a new governor who has also started out swinging. He’s accomplished a lot more in his short time in office than the previous governor did in his time. One of the biggest things is passing a budget. The state of Illinois went for years; that again preceded me, but went for years without passing a state budget. 

So, I think he’s really thought about what he wants to do. The fact that he’s looking and is really pushing for a progressive income tax, which could have a huge impact on these issues of equity. It has to be done right. It has to be done in a way that makes sure that it balances the needs of the whole population. But I think the fact that he’s come in with a point of view, that he also is very focused on issues of justice and equity, I think means that we’ve got a lot of reason for optimism for those of us who really care about these issues. 

Of all the cities I’ve ever lived in, and I’ve lived in a few, it is the most civically-minded city. It has a real spirit of collaboration, and people really love their city. I have never been in a city with this much civic pride. People bleed Chicago, if you will.

Denver: Helene, Chicago has a reputation of being one of the most collaborative philanthropic communities in the country. Have you found that to be the case? What’s been your general impression of the city and how it operates after a couple of years?

Helene: It’s one of the things that has struck me the most, coming in. Of all the cities I’ve ever lived in, and I’ve lived in a few, it is the most civically-minded city. It has a real spirit of collaboration, and people really love their city. I have never been in a city with this much civic pride. People bleed Chicago, if you will. And so, that is incredibly optimistic. 

But I still worry about how divided the city is, and how little different parts of the city know about each other. And, again, I think it’s a role that we can play as The Chicago Community Trust: How do we bring people together? How do you develop that kind of sense of proximity, so that people actually develop empathy and develop an understanding of what will change to make this a city that works for all. I think that’s what we all want – a city that works for all, not a city that works really well for some. But how do we make it a city that works well for all? And I think that’s what every Chicagoan actually wants; it’s just not always clear what it takes to get there. 

…what that election showed is that we had become more and more divided as a country. I started realizing that if I looked at my career on the global stage, the United States has always been a beacon for the rest of the world. We can no longer be a beacon for the rest of the world if we’re coming apart at the seams.

Denver: As I mentioned a little bit in the opening, you were trained as a pediatrician; then you got into public health. And as you look at your career trajectory, I don’t think anybody could have plotted how one thing led to another. Walk us through it a little bit as to how you got to where you’re at right now.

Helene: Well, you’re right. Had I thought 30-some years ago when I was finishing my training as a pediatrician that I would end up running a community foundation, in between running a global nonprofit, and doing global philanthropy, and working for the government for 20 years, who would have known? 

But I guess for me, I think I always had a central core and kind of overarching values that led me along the way.

I went into medicine because I wanted to have a tangible way in which I could make a difference. I grew up at a time in our nation where we were going through incredible social change, whether it was the civil rights movement, women’s movement, anti-apartheid…all these kinds of big sweeping social changes that really had a real impact on me as I was growing up. I grew up with a sense of wanting to make a contribution, give back, and hopefully have an impact at a large scale.

So when I went into medicine, I realized that as a  clinician, you can really make an impact on individuals’ lives, but if you focus on something like public health, you can actually have an impact at a population level. So, I went from thinking about individual impact in health to more of a population level. But the longer I was in public health, both at a national and then global level, I started realizing that at the end of the day, as we talked about earlier, a lot of the disparities in health are really more about the underlying social causes and economic inequality… other systemic ways that marginalize and hold people back.  And if you don’t focus on some of those root causes, you’re not going to be able to impact health either. And so that kind of led me to my work at CARE, where we focused on global poverty and all of those root causes of economic, education, social stigma, gender inequality, et cetera. And so I think that “How do you keep digging beyond the surface to getting at the root causes?” has always been at the core of my career and my trajectory. 

I think in a lot of ways for me, just like so many people, the 2016 election was a real wake-up call. And not to make this partisan, but I think that what that election showed is that we had become more and more divided as a country. I started realizing that if I looked at my career on the global stage, the United States has always been a beacon for the rest of the world. We can no longer be a beacon for the rest of the world if we’re coming apart at the seams. 

And so it made me feel like I needed to commit myself to making a difference here in the United States, and looking and addressing some of the very issues that kind of got me on this path to begin with – issues of inequity, social justice, race, and the role that race plays in America. So, I guess in some ways, it’s full circle, but it’s always been about: How do we create a more just, equitable world? How do we allow all people to participate in it and be able to realize their full potential? How do we link the global to the domestic in ways that can really make us all a better world? 

I want to be a part of making sure that Chicago can achieve its full potential, but I also think that it’s a city that people look to for leadership. And so, I think that if we can get some of these issues right in Chicago, it can have an impact. It can be an example for the rest of the nation, and maybe even the rest of the world on: What does it take to allow people to all participate equally?  And I think it’s a task worth focusing on. 

Denver: In many ways, it’s one of the first opportunities you’ve had to make a real impact in the community in which you live, and that’s actually pretty cool.

Helene: It is! I get up every morning, and I’m excited because I walk out of my door and feel like the people I see in the streets, maybe somehow, I can have an impact, and in such a city that is such an incredible city, that has brought so much to the nation, into the world. I want to be a part of making sure that Chicago can achieve its full potential, but I also think that it’s a city that people look to for leadership. And so, I think that if we can get some of these issues right in Chicago, it can have an impact. It can be an example for the rest of the nation, and maybe even the rest of the world on:  What does it take to allow people to all participate equally? And I think it’s a task worth focusing on. 

Denver: Well, we’re glad you’re the one focusing on it, I’ll tell you that. Dr. Helene Gayle, the Chief Executive Officer and President of the Chicago Community Trust, I want to thank you so much for being here this evening. For people listening, who would like to learn a little more about the Trust and the work you’re engaged in, tell us about your website and what people will find on it. 

Helene: So, if you go to our website, which is cct.org, I think you’ll find a lot about the programs, the history of The Chicago Community Trust, and a lot of the ways in which we’re really trying to bring voice to the communities that we serve. You’ll see a lot about our work within the communities, but we also have a lot of information that is important for donors. It gives information on how people can contribute to The Chicago Community Trust and its mission. So we want to serve both our donors, as well as our community, and hopefully be a source of information about what’s going right in Chicago, and how we can all join together to make Chicago the city that we believe it can be. 

Denver: Thanks, Helene. It was a real pleasure to have you on the show.

Helene: Thank you. Great to be with you again. 

Denver: I’ll be back with more of The Business of Giving right after this.

Dr. Helene Gayle and Denver Frederick


The Business of Giving can be heard every Sunday evening between 6:00 p.m. and 7:00 p.m. Eastern on AM 970 The Answer in New York and on iHeartRadio. You can follow us @bizofgive on Twitter, @bizofgive on Instagram and at www.facebook.com/businessofgiving.

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