Staff

Jessica Caffrey, Executive Director | jessica@cookcountylandbank.org

Jessica Caffrey is a Chicago real estate and community-development executive whose career has been defined by a fundamental belief that investment in places must also be investment in the people who live there. Over more than two decades working at the intersection of finance, real estate, government and community development, she has helped transform underused public assets into accessible housing, economic opportunity and stronger neighborhoods.

Since becoming executive director of the Cook County Land Bank Authority in December 2022, Caffrey has led the transformation of one of the nation’s largest land banks, which operates countywide across a region of 5.2 million people and 134 municipalities. Traditionally an organization chiefly associated with acquiring and disposing of distressed property, it is now a catalyst for equitable redevelopment that has generated $300 million in community wealth since its inception.

As Cook County currently has 38,765 severely tax-delinquent properties, and recent property-tax reforms create the potential to return thousands of them to productive use at scale, CCLBA’s mission places her at the center of one of the most significant public-land opportunities in the country. For Caffrey, that challenge is deeply personal. Born and raised on Chicago’s South Side, she spent her early years in Auburn Gresham and grew up in Calumet Heights. Those roots inform an approach to development that looks beyond individual real estate transactions to what investment can mean for a block, a family or a community. From her work in community development, she has found that properties others see as “eyesores” can become community “cornerstones.” Her goal for CCLBA is equally ambitious: to turn vacant and distressed land into community wealth and generational wealth, particularly in neighborhoods that have experienced decades of disinvestment.

Under her leadership, CCLBA has expanded its ambitions and strengthened the institutional capacity required to achieve them. Caffrey has increased financial and operational discipline, strengthened technology and data systems, expanded the team and implemented reforms arising from inherited operational and audit reviews. She points to her record of consecutive clean audits with no material findings as evidence of the effective and stronger accountability culture she has built. At the same time, she has expanded programs that cultivate emerging developers, connect them with lenders, and help local real estate entrepreneurs progress from initial rehab projects with CCLBA to larger portfolios that include several or more properties and new construction.

Her philosophy is captured in a distinction she makes about CCLBA’s work: “A transaction is a closing, but transformational is what happens to that block.” That approach increasingly means looking beyond individual parcels to assemble land strategically around housing, commercial corridors, transit and other community anchors. Recent examples include providing 46 parcels in Roseland for affordable housing and neighborhood revitalization and helping assemble dozens of parcels required for the CTA Red Line Extension, a transformative investment on Chicago’s Far South Side.

Caffrey also commissioned and led CCLBA’s landmark 10-year economic impact analysis, published in 2024. The independent study found that during its first decade, the Land Bank and its development partners generated more than $1.8 billion in direct and indirect economic impact and created or maintained more than 1,400 jobs. Following the 10-year impact report, CCLBA’s annual fiscal report for 2025 was its most successful to date, showing the agency exceeded its performance targets and generated a record $9.6 million in revenue.

Before leading CCLBA, Caffrey served for more than seven years as Cook County’s director of real estate, managing approximately 19 million square feet of County-owned real estate across a 234-property portfolio and playing a leadership role in the redevelopment of the historic Old Cook County Hospital. Earlier, as a development manager at the Chicago Housing Authority, she oversaw complex public-housing redevelopment and worked directly with residents, elected officials and community leaders. During her tenure at CHA, she directed a $200 million program that created more than 11,800 mixed-income housing units.

Those experiences shaped a leadership philosophy centered on participation and access: residents should be able to live in their communities, work in their communities and benefit from the investment occurring around them. Caffrey brings the same philosophy to CCLBA’s developer pipeline, where increasing local development capacity has become one of her most important efforts. Through quarterly Working With the Land Bank seminars that draw roughly 100 to 250 participants, CCLBA brings prospective and existing developers together with Land Bank acquisition specialists, City and County economic-development officials and lenders experienced in financing distressed-property redevelopment. Participants learn how to identify available properties, navigate applications, prepare scopes of work and demonstrate proof of funds and, critically, meet the capital providers capable of helping finance their projects.

Caffrey expanded this program when she joined CCLBA because she has seen that success takes more than simply attracting more applicants. True success is helping a first-time developer complete one rehabilitation, return for several more properties and ultimately gain the experience and capacity to undertake new construction and build a broad project portfolio. Mentorship has proved to be one of the most significant aspects of the seminars as Caffrey has enlisted many of the experienced developers who have grown through CCLBA’s pipeline to return to the seminars and share what they have learned with the next generation. In this way, CCLBA is not only expanding the pipeline of properties available for redevelopment; it is expanding the pool of local entrepreneurs capable of redeveloping them.

Caffrey is also expanding CCLBA’s own capacity to meet the coming increase in tax-delinquent properties. Cook County approved six additional positions to strengthen asset management, acquisitions, program management and administration, while Caffrey has also taken measures to upgrade CCLBA’s technology and data systems to prepare for a dramatically larger property pipeline. Together, these investments in people, systems and developer capacity advance Caffrey’s larger goal: to make CCLBA a national model for how public land can be used to expand opportunity, build generational wealth and give communities the tools to shape their own futures.

A growing national voice on equitable redevelopment, land banking and community wealth creation, Caffrey has spoken at the City Club of Chicago and the National Urban League Conference and is a member of the Urban Land Institute. She holds a bachelor’s degree from DePaul University, a master’s degree in real estate from Roosevelt University and is a graduate of the University of Chicago Civic Leadership Academy.