Les Jacobowitz

Les is a partner in the New York office.
Les Jacobowitz, partner

Les works in the finance, real estate, project finance, health care, and bankruptcy groups. He has nearly 30 years of experience representing a broad range of issuers, underwriters, and financial institutions in domestic and international transactions involving $25 billion or more, as well as restructurings and workouts of an additional $23 billion. Les has also worked with governmental entities, private companies, banks, investment banks and funds in all aspects of financing, including the lending, securitization, real estate, public finance, not-for-profit, energy, and infrastructure financing areas.

He represents clients in diverse transactions involving commercial and economic development, nursing homes, hospitals, assisted living facilities, airports, university and student loans, multifamily and single family housing, stadiums, infrastructure, privatization, energy and utility, resource recovery, and general obligation.

Special Recognitions

In November 2011, he was named in the annual rankings of The Financial Times for his standout innovative work with Fannie Mae, Freddie Mac, The Federal Housing Finance Agency and the US Department of the Treasury in connection with their $24 billion programs to stabilize the housing finance market. Les worked on an international toll bridge facility that was selected by the Institutional Investor as one of its deals of the year.

For his work coordinating and financing nine adult day care facilities for people with AIDS in the city of New York and the surrounding suburbs, he received special recognition from New York state and the AIDS organizations. He also received an award from the Louisiana State Bar Association for his pro bono work with New Orleans Legal Assistance, the Housing Authority of New Orleans, the City Council, and the US Department of Housing and Urban Development to preserve the ownership rights of low income families that had been obtained over the years in their lease-to-own project.

Most recently, he received the Marc L. Fleischaker Pro Bono Award for his work helping the Center for New York City Neighborhoods launch its New York State Mortgage Assistance Program (MAP) with the Office of the New York State Attorney General.  MAP is a loan assistance program funded from the bank settlements stemming from the 2008 financial crisis and targets families trying to avoid foreclosure.

In 2000, Les served on the inaugural trade mission to China sponsored by the U.S. Department of Commerce and the U.S. Department of Housing and Urban Development as normalized U.S./China trade status was debated and enacted by Congress.

Bank Financing & Securitization

Les is experienced in financings involving asset-backed securities (ABS), collateralized debt obligations (CDOs), collateralized loan obligations (CLOs), and commercial mortgage-backed securities (CMBS), representing issuers, investment banks, funds, liquidity banks, and credit enhancers. He helped form the first trust certificate program securitized by low income housing bonds. Les also helped establish the first short-term option certificate program secured by outstanding debt, and securitizations relating to new asset classes such as television rights and timber revenues.

In the origination of several mortgage loans for a large financial institution, Les redrafted all of the loan documents to meet securitization guidelines and used various other closed transactions to provide model documents to best protect the lender in the issuance of the last large CMBS transaction consummated prior to the financial crisis. He has also helped to structure and prepare initial documentation for the securitization of mortgage loans and Real Estate Mortgage Investment Conduits (REMICs), including various forward delivery structures utilizing specially modeled swaps, and large programs involving the securitization of unrated bonds secured by mortgage loans, representing MBIA.

He recently represented Fannie Mae and Freddie Mac in the purchase by the US Department of Treasury of $13.5 billion of GSE securities backed by a portfolio of bonds, and bond liquidity and credit enhanced multistate pooled single family and multifamily transactions of $8 billion, the major successful US initiatives dealing with the recent housing crisis. For both programs, Les drafted many of the template documents and assisted in overseeing program implementation. These transactions involved nearly 100 state and local governmental issuers.

Recently, Les represented a mezzanine lender involving over 200 nursing home and other health-care related properties throughout the United States.  Shortly after closing, the $1.9 billion senior loan was securitized by the senior lenders.

Real Estate

Most of the transactions Les has been involved with have a real estate financing component.

One recent high profile real estate financing transaction included a $450 million financing for a multi-use project (including school, retail, residential rental, and condominium) on behalf of Rose Associates. He also represented the joint venture between Bank of America, N.A. and The Durst Organization to develop, finance, and restructure Bank of America’s new $1.2 billion New York City headquarters building and was instrumental in structuring this complex Liberty Bond financing.

Les assisted Silverstein Properties in the $1.6 billion financing of 3 World Trade Center involving three (3) separate layers of debt and complicated security provisions, including a partial backstop guarantee from The Port Authority of New York and New Jersey, as well as blending bond and CMBS structuring into one transaction. This was the largest unrated tax-exempt transaction ever done, where he represented large mutual funds, real estate funds, and opportunity funds.

He worked on the largest single family residential home sale in the US at the time for $120 million.

Public Finance

Les has served as counsel to issuers, underwriters, institutions, credit enhancers, and purchasers involving all aspects of public finance. He has particular knowledge in the housing, health care, economic development, and energy finance areas, as well as extensive experience in assisted living/senior housing, debt restructurings, education, infrastructure, international, not-for-profit, and privatizations.

He is experienced in the securitization of pools of unrated tax-exempt multifamily housing bonds. He worked on nearly 50 bond financings aggregating to approximately $1.8 billion of tax-exempt and taxable bonds for the New York City Housing Development Corporation. Les was also involved in the state of Connecticut’s first issuance of residual interest bonds and New York state’s first variable rate, multimodal financing. He also handled the following unique transactions in New York: the largest multifamily pooled financing; the first take-out financing of a bankruptcy project; all of the transitional housing facilities for the homeless, and the first two bond bank deals.

Les successfully completed six financings for an innovative homeless program. The bond proceeds from these financings were used to provide financing for the costs of constructing and equipping approximately 600 residential units for occupancy for homeless facilities in New York State. He recently closed a complicated private placement for a parking garage involving a for-profit subsidiary of a hospital through the federal bail-out recovery zone legislation enacted to stimulate the weak economy.

Recently, Les worked on a $175 million financing for a large university, secured by certain of its real estate assets, so as to deal with its liquidity issues.

Bankruptcy, Financial Restructuring & Work-Outs

Les serves as a bridge between the real estate, finance, and bankruptcy groups in work-outs of real estate, finance, and securitization transactions.

Les worked on various restructurings which included, inter alia, the closing of the “open” pooled nature of various programs, and unwinding of securitization programs. He has worked on several work-outs of multifamily housing loan, tax credit, and bond transactions involving extensive negotiation with government issuers, US Department of Housing and Urban Development (HUD), bankruptcy trustees, bond funds, tax credit syndicators, borrowers, underwriters, bond counsel, credit enhancers, bond trustees, and lending institutions.

He also took the lead in a pre-pack bankruptcy involving two securitizations, and worked on all real estate and finance related matters in the Section 363 bankruptcy sale of 12 single family housing developments containing approximately 150 homes from the second largest single family housing developer in New Jersey.

In 2013, Les prepared an in-depth analysis of Puerto Rico that presaged the significant financial troubles relating to its $70 billion in debt and $30 billion in pension liabilities. This included an analysis of (i) the constitutional and statutory framework governing the Commonwealth as a territory, (ii) general obligation and cofina bonds and the nature of their priorities, (iii) various other Commonwealth bonds including those subject to clawback, (iv) pension, pension bonds and OPEBs and (v) the role of GDB in Commonweath financing.

Litigation: Finance & Real Estate

Over the years and, in particular, during the financial crisis, Les has been asked to assist in cases involving real estate lending, bond financing, swaps and securitizations.

Les facilitated the settlement of a structured finance investment with a large foreign banking institution where the underlying fund had been unwound. The case, which involved claims of improper administration of the investment redemption request on the securities as well as failure to substitute the failing underlying securities, triggered by lack of pool diversification and shortfalls in asset thresholds, had been before the US District Court of the Southern District of New York and JAMS.

Another case involving arbitration of a real estate loan with a dispute on appraised value was before two federal district courts and the American Arbitration Association. Les served as both a fact witness, as well as an expert witness, with respect to real estate lending banking practices. In the proceedings, he acted as general counsel to the company overseeing the entire litigation/arbitration process, including brief preparations, AAA panel selection, discovery, deposition prep, and settlement negotiations.

He assisted a municipal entity with the Securities and Exchange Commission’s litigation of improper securities disclosure by the municipality providing an analysis that highlighted the SEC’s significant weaknesses in the case.

Energy & Environment

Les handled numerous energy transactions involving electric generation and micropower electric generation, energy efficiency financings, fuel hedging, resource recovery, renewable energy, solid waste disposal, and transmission facilities. He worked on several series of tax-exempt bonds involving Ogden Martin for mass burn solid waste disposal, resource recovery and electric generation facilities. The initial transaction was one of the first of this type of financing in the nation.

He also worked on the first short-term option certificate program, which involved tax-exempt energy, utility, and pollution control bonds purchased on the secondary market. Les completed the original issuance of bonds for a local industrial development agency for a resource recovery facility and the subsequent conversion of these bonds from a floating to a fixed interest rate. Les assisted a federal governmental entity in the negotiation of a $1 billion fuel hedging arrangement with various large commercial banks.

Les also represents an energy company in its financing of a $500 million solar energy farm in the Pacific Northwest, and a company on the financing and power purchase agreement negotiation relating to the generation of wind power in the Midwest.

Due to water shortages in the eastern part of the State of Washington, especially due to recent climate changes, the State and the US Department of the Interior approved the Yakima River Basin Integrated Plan to enhance the State’s reservoir system. As part of the effort to get all stakeholders to agree to the Plan, the environmental community and the Yakama Nation Tribe required that 50,000 acres of environmentally sensitive land be acquired by the State and set aside so as to mitigate the environmental impact of the water reservoir aspect of the Plan. Les was instrumental in assuring that the acquisition and the related $97 million financing was completed, working with the State’s Department of Ecology, Department of Natural Resources, Department of Fish & Wildlife, Treasurer’s Office, Legislature, and Governor’s Office, as well as the lead not-for-profit organization involved in the acquisition.

Infrastructure & Privatization

In order to deal with the tremendous increase in traffic over its three international bridge crossings due to the enactment of the United States-Canada Free Trade Agreement, the Niagara Falls Bridge Commission developed a 30-year expansion program. Les assisted in the securing of both federal and state tax-exempt status for the Commission’s bonds through the enactment of the Intermodal Surface Transportation Efficiency Act (ISTEA). This deal was selected by the Institutional Investor as one of the four “deals of the year.”

He also represented the Multi-Purpose Stadium Authority of Lackawanna County in its financing for the design, construction, and equipping of a multipurpose stadium facility located in Lackawanna County, Pennsylvania. The stadium, with a seating capacity of approximately 10,380, with expansion to approximately 12,500 for field seating, is now the home to the Scranton Wilkes-Barre Yankees, a Triple A affiliate of The New York Yankees.

He worked as special privatization counsel to the New York City Economic Development Corporation with respect to the disposition of Coney Island, Elmhurst, and Queens Hospitals. This transaction was one of the largest and most complicated privatizations ever undertaken in the United States.

Health Care

Les has more than 25 years of experience with the State of New York’s health care financing authorities. As bond counsel and underwriter’s counsel to the Dormitory Authority of the State of New York and its predecessor, the New York State Medical Care Facilities Finance Agency, he has worked on over 50 financings aggregating over $2 billion. He assisted The City of New York with its financial crunch by completing the issuance of nearly $600 million in Health Facilities Revenue Bonds. This transaction helped save New York City approximately $50 million.

He worked as bond counsel on one of the first publicly financed AIDS facilities in the country and on the first industrial development agency hospital financing under the IDA Reform Act. He represented a fund on a $2 billion health care receivables transaction with Genesis HealthCare Corporation. This transaction, which ultimately closed with another purchaser, revolved around the acquisition and financing of over 200 skilled nursing facilities and assisted living residences around the country.

He also worked on a pooled bond financing for nine AIDS adult day care facilities mostly for facilities located in New York City, with security provided by the State of New York Mortgage Agency. In addition, he handled the sale of two failed nursing homes in Connecticut.


Over the years, Les has represented numerous not-for-profit corporations supporting their corporate, tax, and financing needs. He worked with an entity selling and restructuring a portfolio of four (4) multifamily housing projects, two (2) of which had failed HUD REAC scores. He has also assisted numerous not-for-profit entities in their debt restructuring efforts with their various lending institutions.

Currently, Les is representing The Center for New York City Neighborhoods (Center) in its lead role for provision of counseling services to New York City residents impacted by Hurricane Sandy. In this representation, he has had to negotiate the subcontract between the Center and the overall prime contractor for Hurricane Sandy relief for the City as well as sub-subcontracts with various entities providing direct counseling services to residents due to the magnitude of the counseling relief required, all in conformity with the prime contract.

In addition, the firm is assisted the Center in the launch of its New York State Mortgage Assistance Program (MAP), a loan assistance program targeting families trying to avoid foreclosure. MAP is an enhancement of the Attorney General’s Homeowner Protection Program (HOPP), which provides struggling borrowers with free legal and housing counseling services. Since its launch in October 2012, the three-year, $60 million HOPP program has served more than 28,000 homeowners across the State and is funded, in part, from mortgage securities settlements stemming from the 2008 financial crisis. The national mortgage securities settlement involved the nation’s five (5) largest mortgage servicers, earmarking a minimum of $17 billion for nationwide homeowner relief.