Orlando J. Cabrera


Direct: 202.677.4924
Fax: 202.677.4925
2100 Pennsylvania Avenue NW
Suite 350S
Washington, District of Columbia 20037


Orlando is a partner in the Real Estate practice and co-chair of the Affordable Housing industry team. He is widely recognized as a lawyer of choice in affordable housing for financial institutions, investors, syndicators, developers, public housing authorities, housing finance agencies, community development agencies, cities, and counties. His time at the United States Department of Housing and Urban Development (HUD) has helped him become a problem solver, especially on issues relating to HUD regulatory matters (including Native American housing issues), housing finance agency issues, low-income housing tax credits, private activity bonds, debt financing, non-federal state financing programs, tribal financing programs, and general real estate issues is impressive. As a former Assistant Secretary for Public and Indian Housing at HUD, Orlando’s tremendously helpful insight into affordable housing is invaluable.

During his time as the Assistant Secretary, Orlando oversaw the administration of a US $24 billion program, which included public housing, Section 8 vouchers, moderate rehabilitation (mod rehab), and most federal housing and community development programs for Native American tribes nationwide. Orlando has first-hand experience dealing with Community Development Block Grant – Disaster Recovery issues from working through more than a dozen natural disasters together with the Federal Emergency Management Agency and various state disaster recovery agencies.

Orlando has practical business experience from his time as the Executive Director and Chief Executive Officer of the Florida Housing Finance Corporation, the nation’s fourth-largest housing finance agency. In this position, he developed policies for managing the allocation of the low-income housing tax credit, private activity bonds, HOME Investment Partnership Fund, State Housing Trust Fund, and Local Government Housing Trust Fund. During his tenure at Florida Housing, he also served on the Board of the National Council of State Housing Agencies. Orlando also honed leadership skills as the president and chief executive officer of a major affordable housing developer operating in six states, where he led the company through the 2008 economic downturn and planned, disposed of, financed, constructed, or rehabilitated many affordable housing units.

Orlando is a frequent speaker at affordable housing conferences and often testifies before Congress on affordable housing and community development matters.


  • Handled and negotiated consent agreement in connection with a Fair Housing investigation by the United States Department of Justice for a major national investor in multifamily housing

  • Successfully counseled a major United States city in connection with a Fair Housing dispute with HUD

  • Successfully counseled a public company with respect to False Claims Act litigation undertaken by the United States Department of Justice

  • Represent public housing authorities seeking to recapitalize existing HOPE VI properties in year 15 transactions

  • Represent various public housing authorities seeking to assess risk in Rental Assistance Demonstration transactions

  • Restructured FHA-Insured private activity bonds avoiding bond defaults by a housing finance agency

  • Successfully advised affordable housing developers involved in criminal and civil actions undertaken by the United States Department of Justice and United States Attorneys in various Districts

  • Successfully advised project based contract administrators seeking to compel the United States Department of Housing and Urban Development (HUD) to comply with federal procurement law and keep HUD from unlawfully awarding PBCA contracts

  • Defended a Developer seeking to enforce its rights to equity payments as general partner under various limited partnership agreements

  • Represent Developers in Master Development Agreement negotiations

  • Drafted a close out plan for the largest Community Development Block Grant in US history to date


  • University of Wisconsin-Madison, Doctor of Law
  • University of Michigan, A.B.
  • District of Columbia 2010
  • State of Florida 1991
  • State of Illinois 1989
  • State of Wisconsin 1989
    • American Bar Association
    • District of Columbia Bar Association
    • Illinois State Bar Association
  • English
  • Spanish


  • Best Lawyers in America®, Real Estate Law, 2023-24
  • Orlando is one of only three recipients of the Office of Inspector General’s Golden Eagle Award for Public Integrity.

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