Pride, Progress, and Purpose: A Conversation with Jennie Brier & Ray Crossman

Each June, Pride Month offers a time to celebrate the achievements, contributions, and resilience of LGBTQ communities. An important vehicle for that work is the LGBTQ Community Fund, an initiative of The Chicago Community Trust established in 2010 to provide support and advocacy for the LGBTQ community and organizations across the region.

In recognition of Pride Month, current co-chair Jennie Brier sits down with Ray Crossman, the committee’s longest-serving current member, who joined the fund in 2018. As academics, longtime colleagues and personal friends, they bring both professional insight and personal commitment to their work—Jennie as a historian focused on gender, identity, and the AIDS crisis, and Ray as a psychologist, higher education leader and past university president, and longtime advocate whose own lived experience has shaped his dedication to LGBTQ communities. Together, they reflect on the fund’s evolution, its impact, and what the future may hold.

Ray, what brought you to serve on this committee and for so many years?

Ray: I came to the fund through relationships. I had the good fortune of knowing many of the people who helped start it, folks like Jim Alexander, Patrick Sheahan, and many others who were deeply involved in Chicago’s LGBTQ and philanthropic communities. Those connections grew out of earlier work I’d done at the Center on Halsted and other advocacy and community-building efforts across the city. When I moved to Chicago more than 20 years ago, these were the people doing the work, and over time those relationships turned into an invitation to join this effort.

What’s kept me here is the uniqueness of the fund and the way it operates. There really isn’t another fund like it in the country. We’re able to raise money and then decide how to direct those funds. That includes supporting well-established LGBTQ organizations, but more so, smaller, grassroots groups that don’t have access to consistent resources. There’s a real sense of purpose and impact in our work, and that’s what’s kept me engaged over time.

How did your career in academics prepare you for your role on this committee?

Ray: I’ve been a psychologist, faculty member, and university administrator for nearly 35 years, but what has most informed my work on the fund is my lived experience. I’ve been living with HIV for more than 40 years, and so I understand what structures and systems work, which failed both me and adjacent LGBTQ communities, and what needs to change.

Jennie: My work as a historian who believes that people can and should be historians of their own lives has guided my service on this committee. I am also a scholar of feminism and queer history, and finally, a public servant and clear eyed about what it means to work at (and have been educated at) a public institution like UIC. I think about all this as I move into my first term as co-chair of our committee.

What has been your proudest achievement during your time with the fund?

Ray: We’re a committee of 15, and I’m most proud of our collaboration. Three things stand out from our efforts. First, we’ve grounded our grantmaking in research and community input. We’ve conducted needs assessments over the years and, more recently, held listening sessions with both current and prospective grant partners. That process ensures that we’re not making assumptions about what communities need; we’re hearing it directly and then aligning our funding priorities accordingly. Second, we moved to an annual funding cycle. Increased momentum in our fundraising and deliberations has made grantmaking happen every single year for about 5 years now. And third, during COVID, we made a deliberate shift toward trust-based philanthropy. That meant moving away from project-specific funding and instead supporting general operations. It was an important acknowledgment of our partners’ wisdom and competence.

Is there anything you wish the fund could be doing differently?

Ray: One thing that’s become clearer in recent years is that funding, while essential, is only one part of what organizations need. Through our listening sessions, we heard that many of our grant partners are looking for opportunities to connect with one another. They want spaces where they can share challenges, exchange ideas, and build relationships. In response, we recently hosted a gathering to bring people together, and the response was extraordinary. The level of engagement and energy in the room underscored how much that kind of forum is needed. It was gratifying because it showed that we had listened and responded in a meaningful way – to strengthen the broader ecosystem by fostering connection and collaboration.

Jennie: I was struck by how many of our grant recipients are actively engaged in historical work. While we don’t tend to think about the historical needs of communities, we heard clearly that history means something to people well beyond the academy. LGBTQ communities, and our grant recipients in particular, are doing historical work–thinking about what it means to record, collect and preserve history, history as a glue between community organizations, and how we use history to forge change. They see history as helping them show that they are more than the sum of their parts.

What do you hope to see the fund do in the future?

Jennie: As a pre-cursor to your answer, I will just say,I’d like to see us all imagine different forms of allyship–chosen and biological familial connection. I’m thinking of how to shift our understandings of families such that we all think about our biological and chosen families: you are the parent of a trans-child or your mom’s best friend’s child—your cousin—are all your kin. I think this expanded notion of family is deeply linked to all the work of the Trust.

Ray: We need to continue building generosity here in Chicago, bringing more people into this work, and ensuring that LGBTQ organizations have the support they need to thrive. The fund also plays an important role in shaping how philanthropy shows up, both within the Chicago Community Trust and beyond. That means continuing to center community voices, investing in what works, and advocating for a vision of support that is responsive, inclusive, and forward-looking. If we can continue to grow in those ways, I think the next decade holds a lot of promise.