Jake advises clients on the federal income taxation of domestic and cross-border business transactions and business entities, with an emphasis on secured lending and structured finance.

Jake provides counsel on a broad spectrum of tax matters. He has an active practice structuring and negotiating loan facilities on the borrower and lender side. He also advises on federal income tax issues in asset-backed securitizations, loan acquisitions and other structured finance transactions. He regularly represents market participants in securitized debt and grantor trust offerings, particularly in connection with real estate assets.

Jake provides domestic and international tax planning to financial institutions, private investment funds, REITs and private and public companies, including with respect to trade or business analysis, withholding tax issues, choice of entity considerations and treaty qualification. Additionally, he has experience advising on the federal income tax aspects of equity and high-yield debt offerings, fund formation, lease arrangements and mergers and acquisitions.

On a pro bono basis, Jake has aided Afghan asylum seekers in applying for work authorization and reviewed cases for the Mid-Atlantic Innocence Project’s screening committee. In addition, he has trained military volunteers who assist military families in federal income tax return preparation.

Relevant Experience

  • Advises borrowers and lenders on the tax structuring of loan facilities and the negotiation of tax provisions in loan agreements, including the allocation of tax risks and withholding issues
  • Represents global financial institutions with respect to federal income tax considerations in warehousing facilities for real estate assets
  • Represents issuers, sponsors, underwriters and other parties in connection with the federal income tax aspects of purchases, sales, financing and securitization of forward and reverse performing, reperforming and nonperforming mortgage loans, REO, auto loans and other financial assets, including through bespoke structures
  • Counsels portfolio managers on U.S. trade or business considerations in collateralized loan obligation transactions
  • Advises clients on tax-efficient structures for non-U.S. and tax-exempt investors, including blocker formation and issues regarding FIRPTA, U.S. withholding and UBTI
  • Provides U.S. bilateral tax treaty planning for transnational companies

Awards & Recognition

  • Selected as One to Watch for Tax Law, The Best Lawyers in America, 2022-2024

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