January 30, 2023

Volume XIII, Number 30


January 27, 2023

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COVID-19: Tax Considerations in the Time of the Coronavirus Pandemic - Part 1

We are living in an unprecedented time in which COVID-19, unheard of six months ago, now has grown into a pandemic that significantly impacts all aspects of our daily lives.  The personal toll of the pandemic is reflected in increased rates of illness and death, the widespread cancelling of events, and the increasing ubiquity of working from home.  Not surprisingly, and within a very short period of time, COVID-19 has also significantly impacted the transactional and investment landscape.  Market values of private equity portfolio companies and potential targets are more difficult to ascertain with certainty, and are likely to have declined significantly, causing many potential deals to be placed on hold.  Businesses of all sizes face reduced cash flows which will undoubtedly impact their debt servicing capacity.

Transactional and private-investment-related tax considerations in a bear market are undoubtedly different than those associated with a bull market, but careful tax planning can continue to add meaningful economic value.  As a consequence, tax considerations have suddenly shifted towards concepts such as “loss harvesting”, “cancellation of indebtedness”, etc.  This article, the first installment of a multi-part series that will address transactional and other tax considerations in an economic downturn,  provides a general overview of some of the tax tools that have suddenly become useful in this new environment, as well as some of the tax traps for the unwary that taxpayers are more likely to encounter.  Subsequent articles will address some of these issues in more detail.

General Deal Structuring Considerations

  • Due to uncertainty regarding the valuation of businesses, acquisitions may be structured with increased rollover percentages and earnouts.  Depending on the classification of the target and the acquirer, increased rollover percentages will require careful planning in order to utilize structures that allow for a partial tax-basis step-up.  

  • Declining stock values and the increased use of earnouts may potentially impact the qualification of transactions that previously were eligible for “tax-free reorganization” status.

  • Due to declining stock values, employee stock options may be underwater, in some cases necessitating transaction bonus plans or retention pools in order to incentivize key employees who are critical to facilitating a transaction.

  • As more companies incur tax losses, additional steps may be taken both to preserve those losses and to monetize them in a deal.  Lenders may be able to craft strategies to take control of loss companies while maintaining net operating losses.  Further, sellers may be more receptive to structuring transactions as asset sales if loss carryforwards are available to shield significant amounts of corporate-level tax.

  • Certain limitations on the deductibility of interest are more likely to impact businesses.  Increasing numbers of insolvent businesses will be required to determine whether they may continue to deduct original issue discount (“OID”) and conversely debt holders may have the opportunity to stop accruing OID.

  • Disposing of worthless assets may give rise to tax deductions.


  • Debt restructurings (including debt amendments and debt-for-equity swaps) can potentially be taxable events that cause taxable income for the borrower and lender.  Borrowers faced with defaults should consider cancellation of indebtedness mitigation strategies prior to engaging in any restructurings.

  • Depressed asset values present an opportunity for internal group restructurings to occur with minimal taxable gain, and to structure transactions to allow for the harvesting of tax losses.

  • Guarantors may be called upon to make payments on the debt of insolvent issuers.

Fund Structuring

  • Distressed debt investments, which give rise to unique tax issues related to effectively connected income (“ECI”) and the market discount rules, are likely to become more common.  Secondary debt purchasers that traditionally did not have ECI concerns will need to address ECI that may result from significant modifications.

  • Clawback provisions in private equity funds are more likely to be utilized.

  • Previously-issued profits interests are more likely to be underwater.

  • More foreign companies may become subject to the passive foreign investment company (“PFIC”) rules.

  • Investment funds may be required to involuntarily reduce the tax basis in their assets.

Policy Considerations

  • Pending federal legislation will impact the liquidity of companies, their ability to monetize losses, and mitigate the cost of capital.   Examples of such pending legislation include proposals providing loans and loan guarantees to distressed businesses, to reinstate net operating loss carrybacks and allow refundability of business credits, and to increase the limitation on deductible interest expense.  This could be significant for certain acquisitive and other transactions.  For example, an increase in the limitations on deductible interest expense can make debt financing for an acquisition more attractive.  Alternatively, a relaxation on the limitations on the use of NOLs in connection with an ownership change may enable sellers to extract value for their NOLs.  While the final outcome of these proposals is yet to be decided, the White House and Congress are moving quickly to finalize a relief package. We are in the early stages of the policy implications, and it’s not too late to engage in legislative discussions with the appropriate stakeholders.

Copyright 2023 K & L GatesNational Law Review, Volume X, Number 80

About this Author

Adam Tejeda, KL Gates Law Firm, New York, Tax Law Attorney

Mr. Tejeda counsels clients on a wide range of tax matters associated with domestic and international business transactions. He focuses his practice primarily on tax planning in connection with inbound and outbound investments; cross-border financings; domestic and cross-border mergers and acquisitions; multinational IP planning; advising US based clients with regards to Subpart F; corporate and tax aspects of joint ventures and other partnership issues; hedge fund and private equity fund structures; tax planning with respect to the tax consequences of overseas...

Mary Baker Burke, KL Gates Law Firm, Tax Attorney
Government Affairs Advisor

Mary Burke Baker is a government affairs advisor in the Washington, D.C. office. Mary focuses on federal tax matters affecting businesses—including domestic and multi-national corporations and all types of pass-through entities—and individuals. Her practice covers tax policy, tax reform, regulatory and other guidance, tax administration and technical tax issues, with particular emphasis on the OECD and the European Union, accounting methods, energy and medical device issues, and FBAR compliance matters for individuals.

Mary consults with and...

Jay Buchman Tax Lawyer K&L Gates Law Firm

Jay advises clients on the tax aspects of a broad range of domestic and international transactions. In particular, Mr. Buchman focuses his practice on advising private investment funds on a broad range of matters related to fund formation and operation, as well as on domestic and cross-border mergers and acquisitions, financings and joint ventures. Mr. Buchman also advises clients on the Opportunity Zone (OZ) provisions in the Tax Cuts and Jobs Act.