Opportunities for Strategic Debt Repurchases

February 15, 2017

In the current environment of heightened market uncertainty and potential interest-rate changes, opportunities are emerging for companies to take advantage of market prices to reduce their liability profile through the strategic repurchase of outstanding debt securities from debtholders seeking liquidity or quicker returns. For companies with available cash holdings or the ability to raise additional debt or equity capital, strategic debt repurchases may provide a cost-effective and efficient means of canceling outstanding debt, capturing discounts to par, reducing interest expense, enhancing strategic flexibility by deleveraging and potentially removing restrictive covenants, or potentially improving the company’s debt rating.

How best to effect debt repurchases

Cash repurchases of debt generally can be structured as open-market or private repurchases, cash tender offers, or redemptions pursuant to the contractual terms of the governing indenture. These methods vary in terms of implementation time, cost, and the portion of a given debt series that can be repurchased at one time. The scale of repurchases and the structure used may also depend on restrictive covenants in the company’s indentures and other agreements, as well as the availability of operating losses to offset any taxable gains resulting from the repurchases.

Open-market or private repurchases

A company can repurchase debt securities on the open market or through privately negotiated transactions, either directly or through an intermediary. However, such transactions must be structured in terms of timing and quantity so as to avoid triggering a de facto, or “creeping,” tender offer. This method allows companies to benefit from market volatility to repurchase an amount of securities discretely, quickly, and at a discount, with limited or no documentation.

Cash tender offers

Initiating a public tender offer allows a company to purchase up to an entire series of debt in a public transaction available to all debtholders, but also requires compliance with a number of regulations under the securities laws. Tender offers can be effected through a variety of structures intended to encourage efficient pricing and investor participation:

  • Early tender premiums. To incentivize early participation, early-tender premiums can be offered for tenders early in the tender-offer period.
  • Modified Dutch auction. A company can retain a degree of flexibility in the tender price and quantity by using a “modified Dutch auction,” whereby the company specifies a tender price range within which debtholders may tender their securities. The company then decides on a tender price according to the number of securities that debtholders have agreed to tender at that price.
  • Fixed spread. Alternatively, a company can set the tender price based on a fixed spread over the yield to maturity of a reference security (usually a US Treasury bond) with a corresponding maturity. This provides a degree of protection against interest-rate fluctuation during the time the tender offer is open.
  • Waterfall structure. Where there are multiple classes of debt securities outstanding, a company can make an offer for a maximum aggregate dollar value of all or select classes of debt with designated priorities.
  • Consent solicitation. Debt tender offers can also be conducted in connection with consent solicitations, whereby the company’s debtholders are solicited to agree to an amendment to restrictive covenants or other provisions of the underlying indenture.


The most straightforward, but also generally the most expensive, method of repurchasing debt securities is to exercise the redemption provisions built into the underlying indenture. The pre-agreed procedures in the redemption provisions of the indenture set forth a clear and certain process that can be accomplished quickly and without the need for new documentation.

Disclosure considerations and 10b5-1 plans

To mitigate potential risks, an issuer needs to consider whether it possesses “material non-public information” (MNPI) and must be cognizant of the timing of earnings releases and potential corporate developments such as strategic transactions. During a tender offer, these considerations sometimes require a company to delay or accelerate launch, extend deadlines, or provide supplemental disclosures.

One way to provide flexibility in implementing a debt repurchase is to establish a repurchase plan pursuant to Rule 10b5-1 of the Securities Exchange Act (a “10b5-1 repurchase plan”). A 10b5-1 repurchase plan is a written, prearranged plan setting out a schedule for repurchasing securities. As long as a 10b5-1 repurchase plan is adopted at a time when a company is not in possession of MNPI, the automated repurchases carried out pursuant to the plan will not be considered to have been completed on the basis of MNPI, even if the company subsequently comes into possession of MNPI during the course of the plan. Specified limits on repurchases under a 10b5-1 repurchase plan may be included to help avoid triggering a “creeping” tender offer.

Tax considerations

The repurchase by a company of its outstanding debt securities at a discount generally gives rise to cancellation of debt income (CODI) and a reduction in net operating losses (subject to certain exceptions for bankrupt or insolvent companies). The amount of CODI is generally the difference between the principal amount of the debt repurchased (or its accreted value, if applicable) and the repurchase price.

Summary of debt repurchase structures

 Open-market or
 private repurchases

 Cash tender offer  Redemption


Low to none  High  High (generally equal to
 outstanding principal plus
 a premium) 

 Speed of
 Fast  Slow — must stay open
 for 20 business days,
 but may include an early
 settlement date and, in
 some cases, can be
 reduced to five business
 Fast, but can only be
 effected at prescribed
 times pursuant to the
 governing indenture

 Minimal to none  Tender-offer disclosure
 statement and related
 Flexibility in terms of how
 much to repurchase and
 from whom
 Allows entire classes of
 debt to be purchased at
 once for a designated price
 Provides a pre- negotiated
 procedure for retiring all
 or a portion of an entire
 class of debt
 May only purchase a
 portion of outstanding debt
 over a certain period in
 order to avoid triggering
 a tender offer
 Must comply with tender-offer
 rules under the securities
 laws, including offering to
 all debtholders; convertible
 debt is subject to additional
 Limited flexibility —
 must follow procedures
 laid out in the indenture

Issuers should consult with their financial, legal, and tax advisors to determine the most effective liability-management strategy for a particular company.

This memorandum is a summary for general information and discussion only and may be considered an advertisement for certain purposes. It is not a full analysis of the matters presented, may not be relied upon as legal advice, and does not purport to represent the views of our clients or the Firm. Eric Sibbitt, an O’Melveny partner licensed to practice law in California and New York, and Adam Ajlouni, an O’Melveny associate licensed to practice law in California and New York, contributed to the content of this newsletter. The views expressed in this newsletter are the views of the authors except as otherwise noted. 

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