Staff

Jessica Caffrey, Executive Director | jessica@cookcountylandbank.org

Jessica Caffrey brings more than two decades of Real Estate leadership and hands-on experience to her role at Cook County Land Bank Authority.  After holding a series of progressive leadership roles within the County Government, she became Executive Director of CCLBA with dynamism and innovative intention. Under Caffrey’s leadership, the Land Bank continues to demonstrate its mission that there is a robust market for naturally occurring affordable housing in every community.

Before leading the CCLBA, Caffrey led the Real Estate portfolio for Cook County’s Offices under the President, which included 234 unique properties that covered over 19 million square feet.  Caffrey spearheaded the redevelopment and rehabilitation of the historically significant Old Cook County Hospital which was transformed into offices and a hotel and helped bring the Cook County Board of Commissioners vision into reality.  Caffrey managed and executed real estate acquisitions and dispositions on behalf of the County, which included negotiations, procurement, and executing all aspects of transitions from valuation to long-term strategic planning.

Before joining Cook County Government in 2012, Caffrey worked for the Chicago Housing Authority where among other responsibilities, she strategically planned and coordinated the redevelopment process for the Oakwood Shores community.  During this time, she managed a $200M redevelopment program to create a mixed-income community at the former Madden Park/Ida B. Wells site, and Altgeld Gardens creating more than 11,800 housing units in the process. As a widely respected real estate leader, Caffrey has a proven track record in successfully managing complex real estate initiatives and devising and implementing comprehensive strategic plans for property development.

Having now led the CCLBA for over a year Caffrey’s diligence has made an ineffaceable mark on the County.  Under Caffrey’s leadership, CCLBA has preserved and increased home values, helped return approximately $5M annually in property tax revenue to Cook County, and induced upwards of $14M in private sector investment in tax-distressed properties.  The result is an estimated $10.02 to $15.86 in economic impact to Cook County during FY 23, for every dollar from the Land Bank’s budget.

Caffrey received her bachelor’s degree from DePaul University and her Master of Science in Real Estate from Roosevelt University. Caffrey is also an alumni fellow of the University of Chicago’s Harris School of Public Policy’s prestigious Civic Leadership Academy. Most importantly, she is a proud mom to two and resides in the City of Chicago.

Darlene Dugo, Associate Director | darlene@cookcountylandbank.org

Darlene A. Dugo joined the Cook County Land Bank Authority in July 2016. She is responsible for overseeing property acquisition and disposition, and developing new strategies to assist the CCLBA acquire new properties and ready these properties for productive use. In this role, she works with other CCLBA staff and outside developers and private and public stakeholders.  In her position, Darlene also provides strategic leadership to the organization as part of the senior management team.

Darlene comes to the Cook County Land Bank Authority from Mercy Portfolio Services, a subsidiary of Mercy Housing, Inc. where she served (2009-2016) as Vice President responsible for operations, management, and oversight of the City of Chicago’s $168 Million Neighborhood Stabilization Program (NSP) Award.

For more than a decade-and-a-half before joining Mercy Portfolio Services, Darlene served as Regional Director, Housing and Community Development for Fannie Mae. Darlene was responsible for business development activities and operations for an 18-state Central Region with 20 Community Business Centers. Working through these centers, she helped to build public and private partnerships with lenders, developers, not-for-profits, housing finance authorities and municipalities.

Darlene received a Master’s of Science in Communications from Northwestern University, and a Bachelor of Arts with a concentration in Finance from DePaul University.  She is a licensed Illinois Real Estate Managing Broker.

Kenneth Gilkes, Jr., Associate Director | kenneth@cookcountylandbank.org

Kenneth Gilkes Jr brings over a decade of experience in real estate, economic development, and public administration to the Cook County Land Bank Authority. With a proven track record of resolving complex problems and driving organizational growth, Kenneth excels in project management, strategic planning, and fostering community partnerships.

Kenneth’s career spans the non-profit, public, and private sectors, focusing on equitable real estate and economic development. As the Director of Real Estate and Economic Development at Community Education Network, he led initiatives for acquiring and developing community assets, including a 400,000-square-foot school campus.

Prior to this, Kenneth served as a Tenant Representation Broker and Senior Analyst for Business and Economic Incentives at Jones Lang LaSalle (JLL), where he negotiated over $500 million in incentives for clients and conducted multi-state comparisons of statutory and discretionary incentives.

In the public sector, Kenneth worked for the City of Chicago’s Department of Planning & Development as a Project Coordinator for Special Service Areas. In this role, he managed multiple portfolios overseeing $4.5 million in economic development funds and implemented dashboard systems to evaluate program effectiveness.

Kenneth holds a Master of Science in Real Estate from Roosevelt University and a Master of Public Administration from the University of Illinois at Chicago. He completed his Bachelor of Arts in U.S. History at Fisk University. He also serves as an Adjunct Professor at Roosevelt University, teaching a graduate-level course on Public-Private Partnerships. In this role, he provides guidance on community engagement strategies, real estate financial analysis, and market evaluation for development projects.

Alex Simmons, Senior Planning Analyst  |  alex@cookcountylandbank.org

Alex Simmons was hired as the CCLBA’s Senior Planning Analyst and is responsible for conducting research, supporting strategic property acquisitions, and serving as the CCLBA’s liaison to planning projects and coalitions in Cook County. He is also responsible for maintaining the CCLBA’s website and providing ArcGIS and other spatial mapping analyses.

Prior to joining the CCLBA, Alex served as the Assistant Planner for the Village of Machesney Park, Illinois, where he conducted plan and building reviews, supervised the ArcGIS Department, and served as the primary zoning official for the Village. Prior to working at the Village, Alex was Planning Associate at Teska Associates, Inc., where he worked on a myriad of planning projects including but not limited to comprehensive planning, TIF, TOD, economic development, and corridor planning.

Alex received his Dual Master’s in Urban Design & Urban Planning from the University of Michigan in 2011, and his Bachelor of Arts in European History in 2008, also from the University of Michigan.

Elisha Sanders, Manager, Property Acquisition | elisha@cookcountylandbank.org

Elisha Sanders joined CCLBA as an Acquisitions Specialist, responsible for specializes in evaluating and acquiring property for the CCLBA.

Elisha joins us with over 16 years of banking experience in corporate and commercial (investment) banking.  Elisha has worked with major and community banks in various roles throughout the loan cycle—originations, monitoring performing and non-performing loans, foreclosures along with the acquisitions of bank owned property.

Elisha strong real estate background, interpersonal skills and knowledge of the community will be invaluable in helping CCLBA make a positive impact on ensuring the mission of CCLBA is accomplished. She also possesses a passion for providing value to the community.

Elisha holds a B.A. in Business Management from Robert Morris University, experience in Grant Writing and she is currently pursuing a Master’s degree in Urban Planning and Policy at The University of Illinois at Chicago.

Anthony Blakely, Senior Property Acquisition Specialist | anthony@cookcountylandbank.org

Tony joined the CCLBA in May 2017 after serving the real estate community in various positions over the last 20 years.  His most recent endeavor was the creation of a real estate company where sales volume grew to $30 M in 8 years.

Prior to entrepreneurship, Tony worked for Fannie Mae as their Middle Regional Field Specialist, covering 11 states within the National Property Disposition Center.  For over a decade, his duties included: REO vendor management, field quality control oversight, property valuation, and marketing issues.  Tony prides himself on, “improving communities one home at a time,” and sees the CCLBA as a broader platform to continue his mission driven work!

Tony holds a Bachelor of Science in Finance from the University of Illinois at Urban-Champaign, and is a licensed Illinois Real Estate Managing Broker.

Gene Kelley, Manager, Real Estate Management | gene@cookcountylandbank.org

Gene Kelley started with Cook County Land Bank Authority in April, 2017.  As a Senior Asset Manager, Gene oversees the preservation of properties acquired by CCLBA until they are sold to an end user for revitalization.  Once sold, Gene monitors the rehabilitation construction of the properties to ensure CCLBA’s standards are being upheld.  In addition, Gene coordinates and supervises the demolition of blight structures acquired by CCLBA.

Prior to joining CCLBA, Gene spent 14 years with Standard Bank and Trust Company in various roles.  Most recently, he managed Standard Bank’s portfolio of REO properties where he was charged with preservation and disposition of the assets.  He also performed draw inspections on a number of Standard Bank’s construction loans.

Gene holds a Bachelor of Science in Business Administration from the University of Illinois at Urbana-Champaign, as well as a Certificate in Construction Management from Purdue University Northwest.

Claudette Shivers, Paralegal | claudette@cookcountylandbank.org

Claudette Shivers joined the CCLBA as a closing specialist with 8+ years’ experience in real estate, delinquent tax properties, REO and distressed properties. She is responsible for assisting with the process of obtaining and drafting the legal documentation for the property acquisitions and dispositions.

Claudette has managed all phases of the closing process from getting transfer tax stamps to obtaining deeds for the client. Throughout her career, in real estate she has successfully closed on over a 1000 properties.

Claudette began working for the County in January of 2015 as a paralegal in the labor division of the Bureau of Human Resources Department. Claudette has a Bachelor’s Degree in Business Administration from the University of Chicago and a paralegal certificate from South Suburban College, an ABA approved program.